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  • Cozy & Serene 1BR Escape
    From $162 per night (USD)

    VRBO

    Cozy & Serene 1BR Escape

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Our charming 1-bedroom apartment features a comfortable living area, a fully equipped kitchen, a bedroom, and ...

    From $162 per night (USD)

    VRBO

    Details
  • Close to Naperville:4BR Home + Parking, Pickleball
    From $350 per night (USD)

    VRBO

    Close to Naperville:4BR Home + Parking, Pickleball

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Make yourself at home in this spacious, fully furnished 4-bedroom townhouse, ready to go. It also comes with a ...

    From $350 per night (USD)

    VRBO

    Details
  • 3BR | Complete & Well-Located Apt in Hyde Park
    From $376 per night (USD)

    VRBO

    3BR | Complete & Well-Located Apt in Hyde Park

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Spacious and comfortable 3BR apartment in the heart of Hyde Park. This fully equipped and thoughtfully furnish ...

    From $376 per night (USD)

    VRBO

    Details
  • Sleek Style 3BR Haven - Free Parking
    From $266 per night (USD)

    VRBO

    Sleek Style 3BR Haven - Free Parking

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: A modern home that’s both stylish and practical, offering comfort and everyday ease. Spacious 3-Bedroom Lay ...

    From $266 per night (USD)

    VRBO

    Details
  • Modern 4BR Rogers Park Stay Near Loyola
    From $372 per night (USD)

    VRBO

    Modern 4BR Rogers Park Stay Near Loyola

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Gather your group and enjoy a comfortable Chicago stay just minutes from Loyola University, Lake Michigan beac ...

    From $372 per night (USD)

    VRBO

    Details
  • Spacious 5-bedroom house great for large groups
    From $665 per night (USD)

    Expedia

    Spacious 5-bedroom house great for large groups

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Light and airy custom built home across from Humboldt Park with expansive views of the Humboldt Park pond/lake. Spacious ...

    From $665 per night (USD)

    Expedia

    Details
  • Large Lakefront Retreat on Pistakee Lake - 6BR/3.5BA
    From $1976 per night (USD)

    VRBO

    Large Lakefront Retreat on Pistakee Lake - 6BR/3.5BA

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    16

    Welcome to your private lakefront escape in McHenry, IL on Pistakee Lake, perfectly situated near Fox Lake and the renow ...

    From $1976 per night (USD)

    VRBO

    Details
  • A chic second-floor plant-filled retreat in Chicago's Logan Square neighborhood.
    From $321 per night (USD)

    Expedia

    A chic second-floor plant-filled retreat in Chicago's Logan Square neighborhood.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Experience the charm of this Logan Square Greystone apartment, a chic second-floor plant-filled retreat in Chicago's vib ...

    From $321 per night (USD)

    Expedia

    Details
  • Charming 3-bedroom cottage with WiFi and AC in beautiful Geneva
    From $355 per night (USD)

    VRBO

    Charming 3-bedroom cottage with WiFi and AC in beautiful Geneva

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Geneva is waiting for you at this 3-bedroom cottage. This fabulous property boasts 1 king bed, 1 sofa bed, and 1 queen b ...

    From $355 per night (USD)

    VRBO

    Details
  • Experience a 3 bedroom historic apartment Rock Island, IL
    From $420 per night (USD)

    Expedia

    Experience a 3 bedroom historic apartment Rock Island, IL

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Nestled in Rock Island, IL, this historic 3 bedroom apartment offers a transformative living experience, blending timele ...

    From $420 per night (USD)

    Expedia

    Details
  • Charming 2-bedroom apartment in fabulous Chicago with WiFi, Game Space
    From $230 per night (USD)

    VRBO

    Charming 2-bedroom apartment in fabulous Chicago with WiFi, Game Space

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to your perfect Chicago getaway! A stylish & spacious Chicago stay perfect for families, friends, couples & busi ...

    From $230 per night (USD)

    VRBO

    Details
  • Serene Oasis Near Rock River | MGM Collection
    From $336 per night (USD)

    Expedia

    Serene Oasis Near Rock River | MGM Collection

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your tranquil retreat in Rockford`s charming north side! Nestled in a peaceful residential neighborhood, our ...

    From $336 per night (USD)

    Expedia

    Details
  • Lakeside Fun and Entertainment!
    From $335 per night (USD)

    VRBO

    Lakeside Fun and Entertainment!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This four bed, three bath home has everything you'll need to enjoy your time at The Lake of Egypt. Equipped with a canoe ...

    From $335 per night (USD)

    VRBO

    Details
  • 1/2 mile to NU, 5min walk to Lake, Swim Spa Pool
    From $909 per night (USD)

    Expedia

    1/2 mile to NU, 5min walk to Lake, Swim Spa Pool

    Bedrooms:
    4
    Bathrooms:
    1
    Sleeps:
    9

    Welcome to one of Evanston`s most distinctive homes, nestled in the historic neighborhood. This spacious 5-bedroom retre ...

    From $909 per night (USD)

    Expedia

    Details
  • Galena Territory | 2BR/2BA Townhome w/ Fireplace & Scenic Views
    From $219 per night (USD)

    VRBO

    Galena Territory | 2BR/2BA Townhome w/ Fireplace & Scenic Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to this cozy 2-bedroom, 2-bath townhome in The Galena Territory—perfect for relaxing, reconnecting, and enjoying ...

    From $219 per night (USD)

    VRBO

    Details
  • Blueground | Elmhurst, pool, nr Elmhurst Art Museum
    From $92 per night (USD)

    VRBO

    Blueground | Elmhurst, pool, nr Elmhurst Art Museum

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this charming Elmhurst furnished one bedroom apart ...

    From $92 per night (USD)

    VRBO

    Details
  • Beautiful Water Front Homes With Lake/ Dock Access
    From $810 per night (USD)

    VRBO

    Beautiful Water Front Homes With Lake/ Dock Access

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    20

    Bring the whole family...and someone else's! These neighboring homes sit in Chapman Cove on The Lake of Egypt. Waterfron ...

    From $810 per night (USD)

    VRBO

    Details
  • 3BR Spacious Apartment in Chicago
    From $345 per night (USD)

    VRBO

    3BR Spacious Apartment in Chicago

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Spacious 3BR/1BA home in vibrant Rogers Park—perfect for up to 6 guests. Enjoy 900 sq ft of bright, comfortable ...

    From $345 per night (USD)

    VRBO

    Details
  • Grafton home located off main street.
    From $1071 per night (USD)

    VRBO

    Grafton home located off main street.

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to Rafton Inn 3! Newly listed as of May 2025, This cozy little home is nestled on a hill that allows a distant ...

    From $1071 per night (USD)

    VRBO

    Details
  • Exclusive Group Getaway in Vibrant West Loop
    From $1738 per night (USD)

    Expedia

    Exclusive Group Getaway in Vibrant West Loop

    Bedrooms:
    8
    Bathrooms:
    9
    Sleeps:
    22

    Summary: 'The Cubist' is the ultimate destination for your group's special occasion, offering four luxurious apartments ...

    From $1738 per night (USD)

    Expedia

    Details
  • Dog Friendly, Steps to Golf, Access to Pools! Adorable Inside and Out!
    From $353 per night (USD)

    VRBO

    Dog Friendly, Steps to Golf, Access to Pools! Adorable Inside and Out!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    <p>This fabulous, dog friendly, 2 bedroom, 2 bath townhome is just steps from the South Golf Course (1 of 4 golf courses ...

    From $353 per night (USD)

    VRBO

    Details
  • Rendelman Orchard's Farm Stay
    From $236 per night (USD)

    Expedia

    Rendelman Orchard's Farm Stay

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Stay at The Cottage at Rendleman Orchards, a remodeled 2BR historic farm home on an 800-acre orchard. Enjoy queen beds, ...

    From $236 per night (USD)

    Expedia

    Details
  • NEW Eco Stay by UChicago, Lakefront & Hyde Park!
    From $271 per night (USD)

    VRBO

    NEW Eco Stay by UChicago, Lakefront & Hyde Park!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy comfort and sustainability in this beautifully designed South Side retreat. Located in a modern, solar-powered gre ...

    From $271 per night (USD)

    VRBO

    Details
  • Brand-New West Loop 3BR + City Views for Families
    From $581 per night (USD)

    Expedia

    Brand-New West Loop 3BR + City Views for Families

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Summary: Experience brand-new luxury at 'The Lyric,' a stunning 3BR in in West Loop’s vibrant Fulton District. You' ...

    From $581 per night (USD)

    Expedia

    Details
  • Blueground | Elmhurst, pool, nr Elmhurst Art Museum
    From $93 per night (USD)

    VRBO

    Blueground | Elmhurst, pool, nr Elmhurst Art Museum

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this stylish Elmhurst furnished one bedroom apartm ...

    From $93 per night (USD)

    VRBO

    Details
  • The Prestige: Designer 3BR/2BA in Prime Location
    From $401 per night (USD)

    Expedia

    The Prestige: Designer 3BR/2BA in Prime Location

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to The Prestige- where luxury meets comfort. This spacious 3-bed, 2-bath condo sleeps 8 (3 king beds & 1 pull-ou ...

    From $401 per night (USD)

    Expedia

    Details
  • Luxury Unit with Rooftop Lounge & Spectacular City Views
    From $256 per night (USD)

    VRBO

    Luxury Unit with Rooftop Lounge & Spectacular City Views

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This listing is for a room within a hotel. ✦ Your room is 248 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...

    From $256 per night (USD)

    VRBO

    Details
  • Charming 2-Bedroom Apt. King Bed, Desk, Fast WiFi, A/C, Near Hospitals
    From $122 per night (USD)

    Expedia

    Charming 2-Bedroom Apt. King Bed, Desk, Fast WiFi, A/C, Near Hospitals

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy comforts of home in this recently updated, 1st floor, private 2-bedroom condo in the SW Chicago Suburbs. We offer ...

    From $122 per night (USD)

    Expedia

    Details
  • Galena Home with Golf Course View
    From $604 per night (USD)

    VRBO

    Galena Home with Golf Course View

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    This 5-bedroom, 6-beds home. It accommodates up to 12 people. We are family-friendly and dog-friendly. -6 Person hot t ...

    From $604 per night (USD)

    VRBO

    Details
  • Cozy 3BR Home – Family-Friendly, Near Schaumburg
    From $393 per night (USD)

    VRBO

    Cozy 3BR Home – Family-Friendly, Near Schaumburg

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your cozy retreat in Streamwood, IL. This inviting and thoughtfully home is perfect for families, business tr ...

    From $393 per night (USD)

    VRBO

    Details
  • Stunning Waterfront Rooftop in Heritage Harbor Sleeps 10-11!
    From $1073 per night (USD)

    VRBO

    Stunning Waterfront Rooftop in Heritage Harbor Sleeps 10-11!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    10

    Welcome to the Coast Carpe Diem! A stunning coastal-style retreat nestled along the harbor front with 360 degree roofto ...

    From $1073 per night (USD)

    VRBO

    Details
  • Eagle's Nest: 3 Bedroom Home in The Galena Territory
    From $467 per night (USD)

    Expedia

    Eagle's Nest: 3 Bedroom Home in The Galena Territory

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to the EAGLE'S NEST. Views for miles! Bright and airy 4 bed, 2 bath Galena Territory retreat that offers absolu ...

    From $467 per night (USD)

    Expedia

    Details
  • 1 Bedroom, 1 bath Condo in The Galena Territory
    From $221 per night (USD)

    VRBO

    1 Bedroom, 1 bath Condo in The Galena Territory

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the heart of the resort core you will find this lovely Long Bay Point Condo. It's located just a short distan ...

    From $221 per night (USD)

    VRBO

    Details
  • Guest suite sleeps 19 with 7 bedrooms just 10 miles from the U of I!!
    From $963 per night (USD)

    Expedia

    Guest suite sleeps 19 with 7 bedrooms just 10 miles from the U of I!!

    Bedrooms:
    4
    Bathrooms:
    7
    Sleeps:
    18

    Get ready to relax in this enchanting 4,000 sq foot 7-bedroom suite in Saint Joseph. With two king beds, one sofa bed, t ...

    From $963 per night (USD)

    Expedia

    Details
  • 4 bedroom, 4 bath house with multiple living areas in Galena Territory
    From $511 per night (USD)

    VRBO

    4 bedroom, 4 bath house with multiple living areas in Galena Territory

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Escape to a lovely 4-bedroom, 4 bath house in Galena Territory. This delightful property features 3 king beds, 2 twin be ...

    From $511 per night (USD)

    VRBO

    Details
  • Wembley Place Estate/Indoor Pool/Hot Tub/Game Room
    From $967 per night (USD)

    Expedia

    Wembley Place Estate/Indoor Pool/Hot Tub/Game Room

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    18

    Summary: Experience unmatched luxury in this stunning 8,000+ sq ft estate featuring soaring 9-ft ceilings and endless e ...

    From $967 per night (USD)

    Expedia

    Details
  • Come experience The Lake Shore!
    From $321 per night (USD)

    VRBO

    Come experience The Lake Shore!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Come experience the Lake Shore! A corporate apartment that boast comfort, class and the PERFECT location to explore any ...

    From $321 per night (USD)

    VRBO

    Details
  • Hot Tub 2-BDRM, 2 full bath all comforts of home in Galena countryside
    From $497 per night (USD)

    Expedia

    Hot Tub 2-BDRM, 2 full bath all comforts of home in Galena countryside

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Cozying up to a fire or soaking in the hot tub next to a firepit is exactly what you need. Our fully renovated historic ...

    From $497 per night (USD)

    Expedia

    Details
  • Charming Cozy 2BR Haven w/Crib Near Hip WickerPark
    From $207 per night (USD)

    VRBO

    Charming Cozy 2BR Haven w/Crib Near Hip WickerPark

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    2B1B unit for 6 people plus a crib. Great West Wicker Park location (in coveted 60622 area code) just 0.9 miles from Dam ...

    From $207 per night (USD)

    VRBO

    Details
  • Cute & Cozy, 1bd Condo Apartment/townhouse
    From $253 per night (USD)

    Expedia

    Cute & Cozy, 1bd Condo Apartment/townhouse

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Enjoy a stylish experience at this centrally-located place. Unique split-level 1-bedroom condo with modern upgrades, sta ...

    From $253 per night (USD)

    Expedia

    Details
  • Lovely Garden Set up is Perfect for Your Morning Coffee or a Drink After Some Great Blues Music at Kingston Mines by AllSet Turnover
    From $426 per night (USD)

    VRBO

    Lovely Garden Set up is Perfect for Your Morning Coffee or a Drink After Some Great Blues Music at Kingston Mines by AllSet Turnover

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This perfectly located 2 BD/2 BA unit is waiting for you to call it home for your trip to gorgeous Lincoln Park! Make y ...

    From $426 per night (USD)

    VRBO

    Details
  • Lower level luxury
    From $197 per night (USD)

    Expedia

    Lower level luxury

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover Chicago like a true local in this stylish 2-bedroom lower-level retreat. Perfect for small groups, this tranqui ...

    From $197 per night (USD)

    Expedia

    Details
  • 1 GB Wi-Fi, 1 Reserved Parking Space, Sleeps 4
    From $202 per night (USD)

    VRBO

    1 GB Wi-Fi, 1 Reserved Parking Space, Sleeps 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Stay in this modern 1BR, 1BA apartment in Lakeview, Chicago, perfect for families, friends, or groups of up to ...

    From $202 per night (USD)

    VRBO

    Details
  • Cozy Condo, Sleeps 2!
    From $300 per night (USD)

    Expedia

    Cozy Condo, Sleeps 2!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Stay in the heart of Old Town, Chicago at this stylish 1-bedroom, 1-bathroom condo with a king bed, in-unit la ...

    From $300 per night (USD)

    Expedia

    Details
  • Stylish Sleeps 6 1 Free Parking
    From $274 per night (USD)

    VRBO

    Stylish Sleeps 6 1 Free Parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Stay in this modern 2BR, 1BA apartment in Lakeview, Chicago, perfect for families, friends, or groups of up to ...

    From $274 per night (USD)

    VRBO

    Details
  • Golf Course Oasis·Hot Tub·Family Fun·Club Pool
    From $359 per night (USD)

    Expedia

    Golf Course Oasis·Hot Tub·Family Fun·Club Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    ★ Golden Tee Arcade • Private Hot Tub • Premium King Mattresses • Right on the Fairway ★ Relax, play, and unwind at Seve ...

    From $359 per night (USD)

    Expedia

    Details
  • Right off of Main St in Robinson
    From $221 per night (USD)

    VRBO

    Right off of Main St in Robinson

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Need a simple, clean, and cozy place to stay in Robinson? You'll have the whole place to yourself! 2 Queen Beds, TV with ...

    From $221 per night (USD)

    VRBO

    Details
  • Stylish 3BR Home with Arcade Games Lounge - with private driveway parking.
    From $378 per night (USD)

    Expedia

    Stylish 3BR Home with Arcade Games Lounge - with private driveway parking.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Welcome to this delightful house in Broadview. With a full basement full of playtime arcade machines and three cozy bedr ...

    From $378 per night (USD)

    Expedia

    Details
  • Beautiful Remodeled 3 Bedroom Home Just Outside of St. Louis
    From $206 per night (USD)

    VRBO

    Beautiful Remodeled 3 Bedroom Home Just Outside of St. Louis

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our updated and spacious 3-bedroom split-level home in Granite City! The unique lay-out of this home includes ...

    From $206 per night (USD)

    VRBO

    Details
  • Modern 2BR Apartment in Medical District
    From $138 per night (USD)

    Expedia

    Modern 2BR Apartment in Medical District

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy your stay in this spacious, fully furnished 2-bedroom, 1.5-bath apartment in Chicago’s Medical District. With two ...

    From $138 per night (USD)

    Expedia

    Details
  • Spacious 4-bedroom house in Palatine with hot tub, firepit, and pool table
    From $184 per night (USD)

    VRBO

    Spacious 4-bedroom house in Palatine with hot tub, firepit, and pool table

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Discover this 4-bedroom house in Palatine. Guests will enjoy the entire main floor of this ranch house. They will find a ...

    From $184 per night (USD)

    VRBO

    Details
  • 2 Comfortable Suites Perfect for Families & Groups
    From $283 per night (USD)

    VRBO

    2 Comfortable Suites Perfect for Families & Groups

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    12

    Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...

    From $283 per night (USD)

    VRBO

    Details
  • O'Hare Suite Perfect for Families w/ Free Breakfast & Onsite Heated Pool
    From $149 per night (USD)

    VRBO

    O'Hare Suite Perfect for Families w/ Free Breakfast & Onsite Heated Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...

    From $149 per night (USD)

    VRBO

    Details
  • 2 Clean Suites Ideal for Groups & Families + Convenient Airport Access Nearby
    From $278 per night (USD)

    VRBO

    2 Clean Suites Ideal for Groups & Families + Convenient Airport Access Nearby

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    12

    Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...

    From $278 per night (USD)

    VRBO

    Details
  • Contemporary Suite Near Rosemont Theater, w/ Free Breakfast & Onsite Heated Pool
    From $149 per night (USD)

    VRBO

    Contemporary Suite Near Rosemont Theater, w/ Free Breakfast & Onsite Heated Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...

    From $149 per night (USD)

    VRBO

    Details
  • Relax in 2 Family-Friendly Suites w/ Heated Pool & Hot Breakfast Near Airport
    From $278 per night (USD)

    VRBO

    Relax in 2 Family-Friendly Suites w/ Heated Pool & Hot Breakfast Near Airport

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...

    From $278 per night (USD)

    VRBO

    Details
  • Enjoy A Clean & Quiet Suite w/ Kitchenette & Pool | Minutes from O'Hare Airport
    From $149 per night (USD)

    VRBO

    Enjoy A Clean & Quiet Suite w/ Kitchenette & Pool | Minutes from O'Hare Airport

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...

    From $149 per night (USD)

    VRBO

    Details
  • Experience Quiet Comfort in 2 Family-Friendly Suites w/ Pool & Free Parking
    From $283 per night (USD)

    VRBO

    Experience Quiet Comfort in 2 Family-Friendly Suites w/ Pool & Free Parking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...

    From $283 per night (USD)

    VRBO

    Details
  • Modern Suite w/ Free Breakfast & Onsite Pool Near Cumberland CTA Station
    From $149 per night (USD)

    VRBO

    Modern Suite w/ Free Breakfast & Onsite Pool Near Cumberland CTA Station

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...

    From $149 per night (USD)

    VRBO

    Details
  • Wrigleyville Retreat • 1BR • Sleeps 6 • Full Kitchen
    From $348 per night (USD)

    Expedia

    Wrigleyville Retreat • 1BR • Sleeps 6 • Full Kitchen

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Ruby's Garden is a modern 1BR Near Wrigley Field • 1 Block from the Stadium Sleeps 6 • Full Kitchen • AC • Perfect for S ...

    From $348 per night (USD)

    Expedia

    Details
  • Spacious 5BR 2BA Berwyn Home
    From $435 per night (USD)

    VRBO

    Spacious 5BR 2BA Berwyn Home

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Summary: Bring the whole family to this great place with lots of room for fun. Welcome to this gorgeous fully rehabbed ...

    From $435 per night (USD)

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    Details
  • Near Chicago - Sleeps 10 - Westchester
    From $268 per night (USD)

    Expedia

    Near Chicago - Sleeps 10 - Westchester

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    10

    Summary: 2-bedroom unit in Westchester and room for up to 10 — just 20 minutes from downtown Chicago. *2 bunk beds ( ...

    From $268 per night (USD)

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    Details
  • Exclusive 40 acre retreat w/ Pool & Hot Tub!
    From $781 per night (USD)

    VRBO

    Exclusive 40 acre retreat w/ Pool & Hot Tub!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Your arrival at `The Farm` begins when you pull into the long, private drive lined with stately maple trees. As you roun ...

    From $781 per night (USD)

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  • Clay Street Retreat Entire home in Clinton, Illinois
    From $141 per night (USD)

    Expedia

    Clay Street Retreat Entire home in Clinton, Illinois

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stay comfortably in Clinton at this 1-bedroom house. The charming space features a queen bed and a sofa bed, perfect for ...

    From $141 per night (USD)

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  • 3 Bed, 2 Bath Spacious Galena Home
    From $871 per night (USD)

    VRBO

    3 Bed, 2 Bath Spacious Galena Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Escape to this scenic 3-bedroom, 2-bath retreat in The Galena Territory, where panoramic views, a private hot tub, and p ...

    From $871 per night (USD)

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    Details
  • Bright 3 BR Wicker Park Loft. 5Beds + 2 parking. 4-min walk to Damen Blue Line!
    From $428 per night (USD)

    Expedia

    Bright 3 BR Wicker Park Loft. 5Beds + 2 parking. 4-min walk to Damen Blue Line!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to your bright, design-forward home base in the heart of Wicker Park. This spacious 3-bedroom retreat sleeps gro ...

    From $428 per night (USD)

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    Details
  • Beautiful, Spacious 3BR Ukrainian Village Home w/ Deck, Garage & Room for Groups
    From $817 per night (USD)

    VRBO

    Beautiful, Spacious 3BR Ukrainian Village Home w/ Deck, Garage & Room for Groups

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to a spacious, beautifully furnished home in the heart of Ukrainian Village, designed for families, groups, wedd ...

    From $817 per night (USD)

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    Details
  • Your Logan Square Oasis with Lush Outdoor Haven!
    From $327 per night (USD)

    Expedia

    Your Logan Square Oasis with Lush Outdoor Haven!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Catalpa Court -- located in the heart of Chicago's beautiful Logan Square neighborhood :) Bright and spaciou ...

    From $327 per night (USD)

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    Details
  • Spacious 2BR - 10 mins from Downtown
    From $290 per night (USD)

    VRBO

    Spacious 2BR - 10 mins from Downtown

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your home away from home in Chicago — just 10 minutes from downtown! We’re conveniently located right by the ...

    From $290 per night (USD)

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    Details
  • 1 Mi to Metra: Estate w/ Theater, Game Room & More
    From $1604 per night (USD)

    Expedia

    1 Mi to Metra: Estate w/ Theater, Game Room & More

    Bedrooms:
    7
    Bathrooms:
    4
    Sleeps:
    8

    Wolf & Sub-Zero Appliances | 9,500 Sq Ft | 2 Mi to Glen Town Center Designed for memorable group stays, this Northbrook ...

    From $1604 per night (USD)

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    Details
  • Parisian Inspired Escape - Close to Town & NU
    From $708 per night (USD)

    VRBO

    Parisian Inspired Escape - Close to Town & NU

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your Parisian-inspired Evanston retreat, where curated art, design books, and stylish details meet modern com ...

    From $708 per night (USD)

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    Details
  • Modern Cozy Retreat by O’Hare
    From $293 per night (USD)

    Expedia

    Modern Cozy Retreat by O’Hare

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your modern Des Plaines retreat! This stylish home offers a bright open layout, fast WiFi, fully equipped kit ...

    From $293 per night (USD)

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    Details
  • Two Little Birds • 2 Studios • Firepit • Lake
    From $220 per night (USD)

    VRBO

    Two Little Birds • 2 Studios • Firepit • Lake

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Two Little Birds was designed for connection, comfort, and FUN. You’ll have access to two separate private studios, eac ...

    From $220 per night (USD)

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    Details
  • The Brass Key Residence
    From $465 per night (USD)

    Expedia

    The Brass Key Residence

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Step into The Brass Key Residence, a thoughtfully curated vintage-inspired home filled with antique treasures, timeless ...

    From $465 per night (USD)

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    Details
  • Park Views, Quality Furniture & Central Location
    From $132 per night (USD)

    VRBO

    Park Views, Quality Furniture & Central Location

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    50

    Comfortable furniture, well thought out kitchen and bathroom and the cozy queen size Nectar Hyrbid mattress in the bedro ...

    From $132 per night (USD)

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    Details
  • Haven Suite- Modern 1BR Near Gurnee Mills, Six Flags, Naval Base, Area Hospitals
    From $142 per night (USD)

    Expedia

    Haven Suite- Modern 1BR Near Gurnee Mills, Six Flags, Naval Base, Area Hospitals

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in a peaceful, stylish retreat designed for quiet comfort and effortless stays. This modern lower-level apartment ...

    From $142 per night (USD)

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    Details
  • Massive Queen Anne Mansion for your whole family to stay!
    From $1329 per night (USD)

    VRBO

    Massive Queen Anne Mansion for your whole family to stay!

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    15

    This is your chance to stay in a historic Chicago mansion. This beautiful Queen Anne style mansion has an abundance of c ...

    From $1329 per night (USD)

    VRBO

    Details
  • Designer Loft 4E | Heart of Gold Coast/River North
    From $420 per night (USD)

    Expedia

    Designer Loft 4E | Heart of Gold Coast/River North

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Ch ...

    From $420 per night (USD)

    Expedia

    Details
  • Designer Loft 3E | Heart of Gold Coast/River North
    From $422 per night (USD)

    VRBO

    Designer Loft 3E | Heart of Gold Coast/River North

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Ch ...

    From $422 per night (USD)

    VRBO

    Details
  • Historical Apartment located on Franklin Park
    From $94 per night (USD)

    Expedia

    Historical Apartment located on Franklin Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Comfortable furniture, well thought out kitchen, large walk in shower, and the cozy Nectar Hybrid mattress will have you ...

    From $94 per night (USD)

    Expedia

    Details
  • Spacious Apt | 4 Queen Beds | Free Parking
    From $368 per night (USD)

    VRBO

    Spacious Apt | 4 Queen Beds | Free Parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Modern Chicago apartment in a quiet residential neighborhood, perfect for 8 guests. Features a full kitchen, high-speed ...

    From $368 per night (USD)

    VRBO

    Details
  • 3-bedroom house in delightful Aurora with cool AC and comfort
    From $383 per night (USD)

    Expedia

    3-bedroom house in delightful Aurora with cool AC and comfort

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nestled in Aurora, this beautiful house offers a comfortable retreat for guests seeking a relaxing getaway. With three b ...

    From $383 per night (USD)

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    Details
  • Luxury Retreat in Normal, IL - Movie Theater, Game Room & Hot Tub
    From $448 per night (USD)

    VRBO

    Luxury Retreat in Normal, IL - Movie Theater, Game Room & Hot Tub

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    16

    Welcome to Normal, Proudly Hosted by Together Oasis Homes. Located across from Shepard Park in a peaceful neighborhood ...

    From $448 per night (USD)

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  • Tremendous 2-bedroom bungalow with AC in charming Springfield
    From $157 per night (USD)

    Expedia

    Tremendous 2-bedroom bungalow with AC in charming Springfield

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This 2-bedroom bungalow is perfect for your escape to Springfield. Guests will find a nice queen bed and a twin bed, mak ...

    From $157 per night (USD)

    Expedia

    Details
  • Bohome Reserve:  Chicago Wicker Park • Sauna • Chef's Kitchen • Outdoor Lounging
    From $1756 per night (USD)

    VRBO

    Bohome Reserve: Chicago Wicker Park • Sauna • Chef's Kitchen • Outdoor Lounging

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Designer, plant-infused 4BR/3.5BA home in Wicker Park—crafted for retreat, work, and play. Unwind in the private sauna, ...

    From $1756 per night (USD)

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    Details
  • Spacious 4BR; 2.5BR; en-suite;FL basement;appliances;central air& heat included!
    From $478 per night (USD)

    Expedia

    Spacious 4BR; 2.5BR; en-suite;FL basement;appliances;central air& heat included!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Make yourself at home in this 4-bedroom Chicago townhome retreat. Each bedroom features a comfortable queen bed, perfect ...

    From $478 per night (USD)

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    Details
  • Garden Getaway ADU in Historic Blue Island
    From $228 per night (USD)

    VRBO

    Garden Getaway ADU in Historic Blue Island

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Classic Blue Island Stay Near the Metra If you're planning to explore the Chicago area but want to stay somewhere with ...

    From $228 per night (USD)

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    Details
  • Luxury Cozy Stay-Near Six Flags, Navy Base
    From $257 per night (USD)

    Expedia

    Luxury Cozy Stay-Near Six Flags, Navy Base

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Experience refined comfort in our newly renovated 2BR retreat. Minutes from Six Flags, Gurnee Mills, Naval Station, and ...

    From $257 per night (USD)

    Expedia

    Details
  • King Bed: Deck w/Grill: Fireplace: Smart TVs: Pool + Gym Access: EV Level 2
    From $454 per night (USD)

    VRBO

    King Bed: Deck w/Grill: Fireplace: Smart TVs: Pool + Gym Access: EV Level 2

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    This charming retreat offers a perfect blend of rustic charm and modern comfort. Enjoy stunning forest views, stargazing ...

    From $454 per night (USD)

    VRBO

    Details
  • Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access
    From $190 per night (USD)

    Expedia

    Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Pet friendly w/a fee · Fireplace · Pool access (indoor year-round, outdoor seasonal) · Fast 500 Mbps Wi-Fi · 2 bed · 2 b ...

    From $190 per night (USD)

    Expedia

    Details
  • 4BR Downtown Retreat | Free Street Parking
    From $556 per night (USD)

    VRBO

    4BR Downtown Retreat | Free Street Parking

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Charming Chicago retreat in quiet Bridgeport. This modern 4-bedroom apartment, featuring queen beds, 2 full baths, and a ...

    From $556 per night (USD)

    VRBO

    Details
  • Superb 6-bedroom house on Lake of Egypt. The view is beautiful.
    From $741 per night (USD)

    Expedia

    Superb 6-bedroom house on Lake of Egypt. The view is beautiful.

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    15

    Experience Lake of Egypt in this awesome 6-bedroom house. With 4 bathrooms, everyone has plenty of space to get ready co ...

    From $741 per night (USD)

    Expedia

    Details
  • Wonder Lake Extended-Stay Furnished 30-Day+ Waterfront Estate
    From $162 per night (USD)

    VRBO

    Wonder Lake Extended-Stay Furnished 30-Day+ Waterfront Estate

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    The Lake Shore House at Wonder Lake - `Luxury Lakefront Living. Extended Stays Elevated.` A 4BR/3BA Luxury Wonder Lake W ...

    From $162 per night (USD)

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    Details
  • Ravenswood Loft - Peaceful 2-bedroom apartment in vibrant Chicago
    From $336 per night (USD)

    Expedia

    Ravenswood Loft - Peaceful 2-bedroom apartment in vibrant Chicago

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Charming 2BR in Ravenswood Manor! This cozy, sunlit apartment sleeps 6 and features 2 bedrooms, 1 bath, a full kitchen, ...

    From $336 per night (USD)

    Expedia

    Details
  • Charming pet friendly bed & breakfast with Washer/Dryer and King size Bed
    From $157 per night (USD)

    VRBO

    Charming pet friendly bed & breakfast with Washer/Dryer and King size Bed

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Your cozy getaway awaits in Belleville at this adorable bed & breakfast. Guests can relax in two inviting living rooms, ...

    From $157 per night (USD)

    VRBO

    Details
  • Modern Spacious Retreat with Fast Wi-Fi, Yard & Workspace - 4BR and 2 Full Bath
    From $351 per night (USD)

    Expedia

    Modern Spacious Retreat with Fast Wi-Fi, Yard & Workspace - 4BR and 2 Full Bath

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to your comfortable home away from home! This modern 4-bedroom retreat sleeps up to 8 guests and is fully equipp ...

    From $351 per night (USD)

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    Details
  • Large and conveniently located
    From $416 per night (USD)

    VRBO

    Large and conveniently located

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Located in Chicago, enjoy what this 3-bedroom apartment has to offer. The space features one king bed and two queen beds ...

    From $416 per night (USD)

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    Details
  • Historic Brick Home Near River & Downtown!
    From $306 per night (USD)

    Expedia

    Historic Brick Home Near River & Downtown!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    7

    Step back in time at this beautifully preserved 1878 brick home in the heart of Savanna, where historic charm meets mode ...

    From $306 per night (USD)

    Expedia

    Details
  • Downtown Comfort – 4 Guests & Basement
    From $232 per night (USD)

    VRBO

    Downtown Comfort – 4 Guests & Basement

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy a cozy, family‑friendly stay just minutes from downtown. This 2‑bedroom home sleeps up to 4 guests and offers a br ...

    From $232 per night (USD)

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    Details
  • The Archer Homestead
    From $263 per night (USD)

    Expedia

    The Archer Homestead

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Enjoy a quiet country vibe on the west side of Springfield—just minutes from it all. This home features a brand-new kitc ...

    From $263 per night (USD)

    Expedia

    Details