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  • COMPLETELY REMODELED, BEAUTIFUL LAKE VIEW FLAT!
    From $242 per night (USD)

    VRBO

    COMPLETELY REMODELED, BEAUTIFUL LAKE VIEW FLAT!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    11

    Perfect Lake View location for an AirBnB. SHORT walk to Brown/Red line trains, Wrigley Field, Southport Corridor, and a ...

    From $242 per night (USD)

    VRBO

    Details
  • Suburban Haven: Cozy Escape with a Touch of Luxury
    From $641 per night (USD)

    Expedia

    Suburban Haven: Cozy Escape with a Touch of Luxury

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    16

    This newly updated home is the perfect place to enjoy some peace and quiet. You’ll find plenty of seating for your whole ...

    From $641 per night (USD)

    Expedia

    Details
  • Chic Chinatown Apt w parking!
    From $452 per night (USD)

    VRBO

    Chic Chinatown Apt w parking!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1 ...

    From $452 per night (USD)

    VRBO

    Details
  • Downtown Brookfield Haven
    From $219 per night (USD)

    Expedia

    Downtown Brookfield Haven

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Consider this apartment your home away from home while you visit Brookfield. This adorable property features 3 welcoming ...

    From $219 per night (USD)

    Expedia

    Details
  • Centrally Located Condo with Parking and Deck!
    From $523 per night (USD)

    VRBO

    Centrally Located Condo with Parking and Deck!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    This condo is located with premier neighborhoods in all four directions. Very easy access to the expressway and subway. ...

    From $523 per night (USD)

    VRBO

    Details
  • Spacious 4BR\/2BA – Private Sun Deck In Chicago
    From $836 per night (USD)

    Expedia

    Spacious 4BR\/2BA – Private Sun Deck In Chicago

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Summary: Nestled in the Edgewater neighborhood of Chicago, @TheDreamRentals Skyline Escape is the perfect jumping off po ...

    From $836 per night (USD)

    Expedia

    Details
  • The Lyra: Luxury Group Getaway - Two Penthouses
    From $5540 per night (USD)

    VRBO

    The Lyra: Luxury Group Getaway - Two Penthouses

    Bedrooms:
    7
    Bathrooms:
    8
    Sleeps:
    15

    Summary: Welcome to The Lyra! 2 penthouses located in the same building and floor. With a primer location in The Loop, r ...

    From $5540 per night (USD)

    VRBO

    Details
  • Cozy 1-bedroom with WiFi and AC in charming Logan Square Chicago
    From $84 per night (USD)

    Expedia

    Cozy 1-bedroom with WiFi and AC in charming Logan Square Chicago

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in Chicago, this marvelous apartment is a dream. With a cozy bedroom and a comfortable living room featuring a f ...

    From $84 per night (USD)

    Expedia

    Details
  • Hinsdale Haven, Pet Friendly!
    From $356 per night (USD)

    VRBO

    Hinsdale Haven, Pet Friendly!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Keep it simple at this peaceful and centrally-located place. This one level, fully fenced, pet friendly home is perfect ...

    From $356 per night (USD)

    VRBO

    Details
  • 3 bedroom Condo on Lagrange
    From $415 per night (USD)

    Expedia

    3 bedroom Condo on Lagrange

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Discover the beauty of La Grange from this 3-bedroom apartment. Each bedroom features a welcoming queen bed, ensuring a ...

    From $415 per night (USD)

    Expedia

    Details
  • Stylish & Comfy 2BR\/2.5BTH condo w\/ Pool and Poker table near Med\/United Center
    From $386 per night (USD)

    VRBO

    Stylish & Comfy 2BR\/2.5BTH condo w\/ Pool and Poker table near Med\/United Center

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    Experience the charm of this spacious "Game House," minutes from downtown Chicago and the United Center! Perfect for rel ...

    From $386 per night (USD)

    VRBO

    Details
  • Modern and Stylish Private1BR Garden Apt in Logan Square With Free Parking
    From $108 per night (USD)

    Expedia

    Modern and Stylish Private1BR Garden Apt in Logan Square With Free Parking

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to our cozy and modern West Logan Square garden apartment in one of Chicago's up-and-coming neighborhoods! The ...

    From $108 per night (USD)

    Expedia

    Details
  • Cloud9|Near Millenium Park|The Poppy
    From $2596 per night (USD)

    VRBO

    Cloud9|Near Millenium Park|The Poppy

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    Summary: Welcome to The Poppy! 2 apartments located in the same building. To ensure safety, all guests must pass our scr ...

    From $2596 per night (USD)

    VRBO

    Details
  • Cloud9|5 apartments @Licoln Park|The Walnut
    From $3033 per night (USD)

    Expedia

    Cloud9|5 apartments @Licoln Park|The Walnut

    Bedrooms:
    10
    Bathrooms:
    10
    Sleeps:
    20

    Summary: Welcome to The Walnut. 5 Apartments located in the same building. To ensure safety, all guests must pass our sc ...

    From $3033 per night (USD)

    Expedia

    Details
  • Cloud9 |@TheLoop|Indoor pool|The Pansy
    From $1902 per night (USD)

    VRBO

    Cloud9 |@TheLoop|Indoor pool|The Pansy

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Summary: Welcome to The Lotus! 2 apartments located in the same building. To ensure safety, all guests must pass our scr ...

    From $1902 per night (USD)

    VRBO

    Details
  • Cloud9|6 apartments @Licoln Park|The Willow
    From $3663 per night (USD)

    Expedia

    Cloud9|6 apartments @Licoln Park|The Willow

    Bedrooms:
    12
    Bathrooms:
    12
    Sleeps:
    24

    Summary: Welcome to The Willow. 6 Apartments located in the same building. To ensure safety, all guests must pass our sc ...

    From $3663 per night (USD)

    Expedia

    Details
  • Cloud9|4 Apartments @LincolnPark|The Cedar
    From $2270 per night (USD)

    VRBO

    Cloud9|4 Apartments @LincolnPark|The Cedar

    Bedrooms:
    8
    Bathrooms:
    8
    Sleeps:
    16

    Summary: Welcome to The Cedar. 4 Apartments located in the same building. To ensure safety, all guests must pass our scr ...

    From $2270 per night (USD)

    VRBO

    Details
  • Cloud9|Golf,Gym,CoWorking@LincolnPark|The Ash
    From $1640 per night (USD)

    Expedia

    Cloud9|Golf,Gym,CoWorking@LincolnPark|The Ash

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Welcome to The Ash, 2 Apartments located in the same building. To ensure safety, all guests must pass our scree ...

    From $1640 per night (USD)

    Expedia

    Details
  • Luxury Two-Level Townhouse | Patio | Lincoln Park
    From $1104 per night (USD)

    VRBO

    Luxury Two-Level Townhouse | Patio | Lincoln Park

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    16

    Summary: NEWLY RENOVATED TOWNHOUSE IN THE HEART OF LINCOLN PARK! This private luxury townhouse (duplex) is perfectly lo ...

    From $1104 per night (USD)

    VRBO

    Details
  • Chic 2-Bedroom\/1 Bath Apartment in Fully Renovated Rowhouse
    From $173 per night (USD)

    Expedia

    Chic 2-Bedroom\/1 Bath Apartment in Fully Renovated Rowhouse

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Chicago is waiting for you at this lovely 2-bedroom apartment. This delightful space offers all the comforts you need, f ...

    From $173 per night (USD)

    Expedia

    Details
  • Chic Modern NEW Loft near United Center, UIC\/IMD & Downtown W\/ Street Parking
    From $422 per night (USD)

    VRBO

    Chic Modern NEW Loft near United Center, UIC\/IMD & Downtown W\/ Street Parking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    10

    Discover luxury in our newly renovated 2nd floor loft in Tri-Taylor. With 13-ft ceilings, large windows, brick and moder ...

    From $422 per night (USD)

    VRBO

    Details
  • Charming 2-bedroom 1 bathroom with plunge pool, new gazebo @  Bridgeport Chicago
    From $207 per night (USD)

    Expedia

    Charming 2-bedroom 1 bathroom with plunge pool, new gazebo @ Bridgeport Chicago

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This Chicago unit 2 inviting bedrooms with 1 full bed and 1 bunk bed in Bridgeport . The cozy space includes new gazebo, ...

    From $207 per night (USD)

    Expedia

    Details
  • Spacious 5-bedroom bungalow in delightful Chicago with AC, WiFi
    From $394 per night (USD)

    VRBO

    Spacious 5-bedroom bungalow in delightful Chicago with AC, WiFi

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    Make yourself at home in this 5-bedroom Chicago retreat. This adorable bungalow features 2 queen beds, 2 twin beds, and ...

    From $394 per night (USD)

    VRBO

    Details
  • Cozy Chinatown Apartment w free parking spot!
    From $417 per night (USD)

    Expedia

    Cozy Chinatown Apartment w free parking spot!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1 ...

    From $417 per night (USD)

    Expedia

    Details
  • Spacious, one-level condo next to Jackson Park
    From $330 per night (USD)

    VRBO

    Spacious, one-level condo next to Jackson Park

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Escape to this condo in picturesque Chicago. This beautiful rental features 3 queen beds spread across 3 bedrooms, ensur ...

    From $330 per night (USD)

    VRBO

    Details
  • Matteson Rental
    From $504 per night (USD)

    VRBO

    Matteson Rental

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Beautiful 2200 sq ft home, located in the south suburbs, near Tinley Park and just minutes away from I-57 and I-80! This ...

    From $504 per night (USD)

    VRBO

    Details
  • Chic 2-bedroom condo in amazing Chicago minutes from Lake Michigan
    From $375 per night (USD)

    VRBO

    Chic 2-bedroom condo in amazing Chicago minutes from Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Kick back and relax in this calm, stylish space in the heart of Chicago’s legendary Bronzeville neighborhood. This styl ...

    From $375 per night (USD)

    VRBO

    Details
  • Cozy spacious 1-bedroom condo in enjoyable Forest Park with fitness room, WiFi
    From $80 per night (USD)

    Expedia

    Cozy spacious 1-bedroom condo in enjoyable Forest Park with fitness room, WiFi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This awesome condo in Forest Park is the perfect home base for your trip. With 1 bedroom, a washing machine, fitness roo ...

    From $80 per night (USD)

    Expedia

    Details
  • Chic 2-bedroom apartment in vibrant Chicago with AC, WiFi
    From $367 per night (USD)

    VRBO

    Chic 2-bedroom apartment in vibrant Chicago with AC, WiFi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover the beauty of Chicago from this 2-bedroom apartment. This delightful space features 1 bunk bed and 1 full bed, ...

    From $367 per night (USD)

    VRBO

    Details
  • Wrigleyville 3BD Condo
    From $1590 per night (USD)

    Expedia

    Wrigleyville 3BD Condo

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...

    From $1590 per night (USD)

    Expedia

    Details
  • Wrigleyville Garden 3BR\/9beds Pod
    From $1482 per night (USD)

    VRBO

    Wrigleyville Garden 3BR\/9beds Pod

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...

    From $1482 per night (USD)

    VRBO

    Details
  • Historic Worker's Cottage with Vintage Charm Monthly Rental
    From $75 per night (USD)

    VRBO

    Historic Worker's Cottage with Vintage Charm Monthly Rental

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Cozy and serene, this restored 1880s worker's cottage is the perfect place to explore Chicago. You'll have the entire ho ...

    From $75 per night (USD)

    VRBO

    Details
  • Charming 2-bedroom home in fantastic Winnetka, IL location
    Click For Pricing

    VRBO

    Charming 2-bedroom home in fantastic Winnetka, IL location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located in beautiful Winnetka, IL, this adorable 2 bedroom, 1.5 bath home sits within a fantastic area known as the 'tre ...

    Click For Pricing

    VRBO

    Details
  • Luxury Designer Penthouse Combo |South| Gold Coast
    From $2274 per night (USD)

    Expedia

    Luxury Designer Penthouse Combo |South| Gold Coast

    Bedrooms:
    4
    Bathrooms:
    7
    Sleeps:
    20

    Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...

    From $2274 per night (USD)

    Expedia

    Details
  • Six-Bedrooms in Wrigleyville
    From $3213 per night (USD)

    VRBO

    Six-Bedrooms in Wrigleyville

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    16

    Enjoy the combination of your own 2 apartments in Wrigleyville - the city's center of nightlife, restaurants, and baseba ...

    From $3213 per night (USD)

    VRBO

    Details
  • Luxury Designer Penthouse Combo |North| Gold Coast
    From $2308 per night (USD)

    Expedia

    Luxury Designer Penthouse Combo |North| Gold Coast

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    20

    Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...

    From $2308 per night (USD)

    Expedia

    Details
  • Charming Chicago Apt
    From $362 per night (USD)

    VRBO

    Charming Chicago Apt

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Discover comfort and convenience in this spacious two-bedroom, two-bath apartment, ideally designed to accommod ...

    From $362 per night (USD)

    VRBO

    Details
  • Bliss in Brookfield - 5BR, 3BR
    From $439 per night (USD)

    Expedia

    Bliss in Brookfield - 5BR, 3BR

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    9

    Consider this house your home away from home while you visit Brookfield. This enchanting property boasts 5 bedrooms, inc ...

    From $439 per night (USD)

    Expedia

    Details
  • 3 Bedroomin the Medical Center!
    From $367 per night (USD)

    VRBO

    3 Bedroomin the Medical Center!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Summary: A couple houses off the popular Taylor St which has plenty of restaurants and bars! The Space: 3 Bedrooms 1 Fu ...

    From $367 per night (USD)

    VRBO

    Details
  • South Loop 4 Bedroom apt
    From $516 per night (USD)

    Expedia

    South Loop 4 Bedroom apt

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    9

    Summary: South Loop 4 bedroom apartment with 1.5 bathrooms. We are centrally located and very easy to get anywhere in th ...

    From $516 per night (USD)

    Expedia

    Details
  • Chic 2BR 2BA Condo with Balcony - River North Chicago
    From $793 per night (USD)

    VRBO

    Chic 2BR 2BA Condo with Balcony - River North Chicago

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Welcome to our chic 2-bedroom, 2-bathroom condo located in the vibrant River North neighborhood of Chicago! Per ...

    From $793 per night (USD)

    VRBO

    Details
  • Quick Drive to Downtown Chicago & Early Check-In
    From $418 per night (USD)

    Expedia

    Quick Drive to Downtown Chicago & Early Check-In

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Book your perfect Chicago getaway at this spacious condo, just minutes from downtown and the United Center! Ideal for gr ...

    From $418 per night (USD)

    Expedia

    Details
  • Musician's Quarters\n\nChicago Jazz , Season discount
    From $79 per night (USD)

    VRBO

    Musician's Quarters\n\nChicago Jazz , Season discount

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Host Chester of Musicians Quarters is offering a Super Cheap BACK TO SCHOOL OFFER. $79 PER NIGHT. From August 21st to Au ...

    From $79 per night (USD)

    VRBO

    Details
  • Luxury Designer Penthouse West |Pool| Gold Coast
    From $1049 per night (USD)

    Expedia

    Luxury Designer Penthouse West |Pool| Gold Coast

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center o ...

    From $1049 per night (USD)

    Expedia

    Details
  • 3BR House w\/ Paradise Garden Oasis and private pool in the heart of Schaumburg
    From $323 per night (USD)

    VRBO

    3BR House w\/ Paradise Garden Oasis and private pool in the heart of Schaumburg

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Schaumburg Oasis with a Pool and Hidden Garden, a true gem in the heart of Schaumburg! Uniquely located just ...

    From $323 per night (USD)

    VRBO

    Details
  • Stay Inn South Shore- Pool Table, Arcade, Sleeps 10, Pet Friendly
    From $563 per night (USD)

    Expedia

    Stay Inn South Shore- Pool Table, Arcade, Sleeps 10, Pet Friendly

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to our stylish South Shore retreat, perfect for families and special events. This spacious 4-bedroom, 3-bathroom ...

    From $563 per night (USD)

    Expedia

    Details
  • Landing at Element at Veridian - 1 Bedroom in Schaumburg
    From $170 per night (USD)

    VRBO

    Landing at Element at Veridian - 1 Bedroom in Schaumburg

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Element at Veridian unveils an exceptional portrait of living. A unique fusion of style and sophistication, our apartmen ...

    From $170 per night (USD)

    VRBO

    Details
  • Landing at Element at Veridian - 1 Bedroom in Schaumburg
    From $169 per night (USD)

    Expedia

    Landing at Element at Veridian - 1 Bedroom in Schaumburg

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Element at Veridian unveils an exceptional portrait of living. A unique fusion of style and sophistication, our apartmen ...

    From $169 per night (USD)

    Expedia

    Details
  • Updated 3 Bedroom Chicago Historic Andersonville
    From $510 per night (USD)

    VRBO

    Updated 3 Bedroom Chicago Historic Andersonville

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 3 bedrooms, and is step ...

    From $510 per night (USD)

    VRBO

    Details
  • Walk to the Beach! Theater-Coffee Bar-Games-Gym
    From $605 per night (USD)

    Expedia

    Walk to the Beach! Theater-Coffee Bar-Games-Gym

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    🌟 This property is managed by @LuxuryLodgingSTR , visit us on the web before booking here for extra savings! 🌟 ✨ I hi ...

    From $605 per night (USD)

    Expedia

    Details
  • Luxury Loft Collection 703 - Terrace - River North
    From $1189 per night (USD)

    VRBO

    Luxury Loft Collection 703 - Terrace - River North

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious bui ...

    From $1189 per night (USD)

    VRBO

    Details
  • Pulaski Mahal - Spacious 3bed\/2.5bath with Game Room. Close to Hwy, train.
    From $464 per night (USD)

    Expedia

    Pulaski Mahal - Spacious 3bed\/2.5bath with Game Room. Close to Hwy, train.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking a ...

    From $464 per night (USD)

    Expedia

    Details
  • Stylish 2BR Urban Retreat in River West
    From $420 per night (USD)

    VRBO

    Stylish 2BR Urban Retreat in River West

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Summary: Welcome to our contemporary 2-bedroom, 1-bathroom condo in lively River West. Ideal for business and leisure, t ...

    From $420 per night (USD)

    VRBO

    Details
  • Wrigleyville Suites Room 2
    From $253 per night (USD)

    Expedia

    Wrigleyville Suites Room 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...

    From $253 per night (USD)

    Expedia

    Details
  • Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n
    From $381 per night (USD)

    VRBO

    Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    LOOK FOR THE GREEN DOOR BLACKS IN GREEN LAUNCHES NEXT LEVEL TOURISM IN WOODLAWN In homage to the legendary "Green Boo ...

    From $381 per night (USD)

    VRBO

    Details
  • 2BD\/1 BA with summer patio in quiet Roscoe Village
    From $276 per night (USD)

    Expedia

    2BD\/1 BA with summer patio in quiet Roscoe Village

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/ ...

    From $276 per night (USD)

    Expedia

    Details
  • ❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square
    From $384 per night (USD)

    VRBO

    ❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Welcome to Chicago! Whether you’re in town to seal a business deal or have a short holiday breather, our warm three-bed ...

    From $384 per night (USD)

    VRBO

    Details
  • Bright 3BR\/1BA FREE Parking\/Laundry in Pilsen. Minutes from Downtown
    From $183 per night (USD)

    Expedia

    Bright 3BR\/1BA FREE Parking\/Laundry in Pilsen. Minutes from Downtown

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Escape to the vibrant heart of Pilsen and experience Chicago like a local in our charming home: -Fully equipped, modern ...

    From $183 per night (USD)

    Expedia

    Details
  • Perfect 2BD\/1BA FREE Garage Parking\/Laundry in Pilsen. Minutes to downtown.
    From $192 per night (USD)

    VRBO

    Perfect 2BD\/1BA FREE Garage Parking\/Laundry in Pilsen. Minutes to downtown.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover our 2-bed, 1-bath Pilsen gem! Adorned with local art, a workspace, and free parking & laundry, it's minutes fro ...

    From $192 per night (USD)

    VRBO

    Details
  • Chic River North Condo 2BR 2BA with Private Balcony
    From $886 per night (USD)

    Expedia

    Chic River North Condo 2BR 2BA with Private Balcony

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Summary: Welcome to our riverfront oasis nestled in the vibrant heart of Chicago's trendy River North neighborhood! Thi ...

    From $886 per night (USD)

    Expedia

    Details
  • A Home Away From Home!
    From $346 per night (USD)

    VRBO

    A Home Away From Home!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Discover the allure of this newly renovated Georgian house. Boasting ample space for family enjoyment. With its close pr ...

    From $346 per night (USD)

    VRBO

    Details
  • River North Central Home With Balcony
    From $596 per night (USD)

    Expedia

    River North Central Home With Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Summary: Enjoy a stylish experience at @TheDreamRentals centrally-located home in Chicago's River West neighborhood. Rel ...

    From $596 per night (USD)

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    Details
  • Windy City Welcome
    From $394 per night (USD)

    VRBO

    Windy City Welcome

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    The entire group will benefit from convenient access to various amenities from this centrally situated location. This re ...

    From $394 per night (USD)

    VRBO

    Details
  • Unique Chicago Penthouse Loft - Amazing Deal & Location
    From $421 per night (USD)

    Expedia

    Unique Chicago Penthouse Loft - Amazing Deal & Location

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Ideal for a Chicago getaway, a business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (n ...

    From $421 per night (USD)

    Expedia

    Details
  • Fulton market \/ Noble Square FREE parking, Laundry, 2.5 miles to Mag Mile!
    From $393 per night (USD)

    VRBO

    Fulton market \/ Noble Square FREE parking, Laundry, 2.5 miles to Mag Mile!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    BEST neighborhood in Chicago. This is the 1st real neighborhood west of all the high-rises, walking distance to restaura ...

    From $393 per night (USD)

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    Details
  • Palos Hills Rental
    From $580 per night (USD)

    VRBO

    Palos Hills Rental

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    2300 SF updated home is the GEM of the South suburbs, nestled in between Midway airport and Tinley/Orland Park! Our home ...

    From $580 per night (USD)

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    Details
  • Lincolnwood Rental\n
    From $580 per night (USD)

    VRBO

    Lincolnwood Rental\n

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    2000 SF renovated unit is 20 minutes away from O’hare Airport & 18 min to downtown Chicago! This property has 3 bedrooms ...

    From $580 per night (USD)

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    Details
  • Summit Rental
    From $580 per night (USD)

    VRBO

    Summit Rental

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Summary:   2340 SF renovated home is only 3 miles away from Midway airport, and approx. 16 min from downtown Chicago! Th ...

    From $580 per night (USD)

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    Details
  • Arlington Heights Rental
    From $580 per night (USD)

    VRBO

    Arlington Heights Rental

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2000 SF renovated unit is 20 minutes away from O’Hare Airport & 35 min to downtown Chicago! This property has 4 bedrooms ...

    From $580 per night (USD)

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    Details
  • Elgin Rental- Jay St\n
    From $580 per night (USD)

    VRBO

    Elgin Rental- Jay St\n

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2100 SF renovated unit is 7-9 min away from interstate 90, which takes you straight to O'hare Air & downtown! This prope ...

    From $580 per night (USD)

    VRBO

    Details
  • Chicago Rental - Vernon Ave
    From $270 per night (USD)

    VRBO

    Chicago Rental - Vernon Ave

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    2600 SF renovated unit in the South suburbs, and only 30 minutes south of Downtown Chicago! This property has 5 bedrooms ...

    From $270 per night (USD)

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    Details
  • Berwyn Rental
    From $344 per night (USD)

    VRBO

    Berwyn Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Summary: 1800 SF renovated home is only 5 miles away from Midway airport, and approx 26 min from downtown Chicago! This ...

    From $344 per night (USD)

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    Details
  • Pearly Gates | 3 Bed | Sleeps 5 | w\/ 2-Car Garage
    From $334 per night (USD)

    VRBO

    Pearly Gates | 3 Bed | Sleeps 5 | w\/ 2-Car Garage

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    9

    Summary: The Pearly Gates is located in the heart of Forest Park! Located just 10 miles from downtown Chicago, you can h ...

    From $334 per night (USD)

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    Details
  • Hoffman Estates Rental
    From $464 per night (USD)

    VRBO

    Hoffman Estates Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    1400 SF renovated unit is 7-9 min away from interstate 90, which takes you straight to O’hare Air & downtown! This prope ...

    From $464 per night (USD)

    VRBO

    Details
  • Elk Grove Village Rental - Kingsbridge Rd
    From $464 per night (USD)

    VRBO

    Elk Grove Village Rental - Kingsbridge Rd

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    14

    1800 SF unit is located near O'hare Airport, Schaumburg, and Hoffman Estates, which gives easy access to plenty of bars/ ...

    From $464 per night (USD)

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    Details
  • Sonder The Burnham | One-Bedroom Apartment
    From $200 per night (USD)

    VRBO

    Sonder The Burnham | One-Bedroom Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Burnham is anything but a traditional red brick building. Step inside for modern upgrades with stainless steel appli ...

    From $200 per night (USD)

    VRBO

    Details
  • Des Plaines Rental
    From $464 per night (USD)

    VRBO

    Des Plaines Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary - 1400 SF renovated unit is 11 min away from O'Hare Airport! This property has 3 bedrooms, & 2 bathrooms. Master ...

    From $464 per night (USD)

    VRBO

    Details
  • Spacious 3BR Apt w\/ In-Unit Laundry
    From $354 per night (USD)

    Expedia

    Spacious 3BR Apt w\/ In-Unit Laundry

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    Summary: Discover comfort and style at our fully furnished 3-bedroom apartment. This modern home offers convenience and ...

    From $354 per night (USD)

    Expedia

    Details
  • Orland Park Rental -Huntington Ct
    From $491 per night (USD)

    VRBO

    Orland Park Rental -Huntington Ct

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Ranch home, with 1 car garage and driveway. The home features a spacious master bedroom, which also contains a desk for ...

    From $491 per night (USD)

    VRBO

    Details
  • Elk Grove Village Rental
    From $464 per night (USD)

    VRBO

    Elk Grove Village Rental

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    1900 SF unit is 5 min away from O'hare, and 12 min from downtown Schaumburg, which is like a bustling mini Chicago, incl ...

    From $464 per night (USD)

    VRBO

    Details
  • The Grand Kimball Lodge, Logan Square, Sleeps 14
    From $935 per night (USD)

    VRBO

    The Grand Kimball Lodge, Logan Square, Sleeps 14

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Summary: Welcome to The Grand Kimball Lodge, a truly unique getaway featured in Architectural Digest's "21 Best Chicago ...

    From $935 per night (USD)

    VRBO

    Details
  • Stunning Suite 2 @ Hotel Nemo Downtown
    From $119 per night (USD)

    Expedia

    Stunning Suite 2 @ Hotel Nemo Downtown

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Hotel Nemo is a boutique, corporate guest house stylishly designed for those who want to stay just around the c ...

    From $119 per night (USD)

    Expedia

    Details
  • Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville
    From $223 per night (USD)

    VRBO

    Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our spacious and stylish 3-bedroom, 3-bath condo located in the vibrant, historic Bronzeville community of Ch ...

    From $223 per night (USD)

    VRBO

    Details
  • Splendid Corner 3BR in the Loop | City Views
    From $694 per night (USD)

    Expedia

    Splendid Corner 3BR in the Loop | City Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...

    From $694 per night (USD)

    Expedia

    Details
  • Chicago Rental - W 64th St
    From $294 per night (USD)

    VRBO

    Chicago Rental - W 64th St

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    2200 SF renovated unit in the suburbs of Chicago, and only 30 minutes south of Downtown Chicago! This property has 5 bed ...

    From $294 per night (USD)

    VRBO

    Details
  • Spacious, Clean and Steps from Wrigley Field!
    From $408 per night (USD)

    Expedia

    Spacious, Clean and Steps from Wrigley Field!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy this beautiful space, just minutes away from the very best Chicago has to offer! This condo is walking distance fr ...

    From $408 per night (USD)

    Expedia

    Details
  • South Shore Home Near Lake for long-term stays, corporate travelers, and nurses
    From $163 per night (USD)

    VRBO

    South Shore Home Near Lake for long-term stays, corporate travelers, and nurses

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to our charming brick home in the picturesque South Shore community of Chicago! This fully furnished property of ...

    From $163 per night (USD)

    VRBO

    Details
  • Chicago Rental - W Berwyn Ave\n
    From $295 per night (USD)

    VRBO

    Chicago Rental - W Berwyn Ave\n

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    1800 SF renovated unit in the North suburbs, and only 20 minutes to Downtown Chicago! This property has 4 bedrooms, & 2 ...

    From $295 per night (USD)

    VRBO

    Details
  • Chicago  Rental - Narragansett
    From $294 per night (USD)

    VRBO

    Chicago Rental - Narragansett

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2000 SF renovated unit is 7 minutes away from Midway Air and 20 minutes from downtown! This property has 4 bedrooms, & 2 ...

    From $294 per night (USD)

    VRBO

    Details
  • Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
    From $129 per night (USD)

    Expedia

    Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...

    From $129 per night (USD)

    Expedia

    Details
  • Family union get together
    From $342 per night (USD)

    VRBO

    Family union get together

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy a peaceful and relaxing stay with your loved ones at this cozy suburban lodging. The two interconnected units prov ...

    From $342 per night (USD)

    VRBO

    Details
  • Gorgeous South Loop 2BR w\/ Jacuzzi & Rooftop, nr Colleges, by Blueground
    From $216 per night (USD)

    Expedia

    Gorgeous South Loop 2BR w\/ Jacuzzi & Rooftop, nr Colleges, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the best of Chicago, with this two bedroom apartment in South Loop. with balcony views over the city. It’ll be ...

    From $216 per night (USD)

    Expedia

    Details
  • Wheeling Rental
    From $420 per night (USD)

    VRBO

    Wheeling Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    1450 SF renovated unit is 23 minutes away from O’hare Airport & 35 min to downtown Chicago! This property has 3 bedrooms ...

    From $420 per night (USD)

    VRBO

    Details
  • Arlington Heights Rental
    From $504 per night (USD)

    VRBO

    Arlington Heights Rental

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2000 SF renovated unit is 20 minutes away from O’Hare Airport & 35 min to downtown Chicago! This property has 4 bedrooms ...

    From $504 per night (USD)

    VRBO

    Details
  • Luxury Retreat with Home Theater
    From $1156 per night (USD)

    VRBO

    Luxury Retreat with Home Theater

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    16

    Summary: Welcome to @TheDreamRentals opulent 5-bedroom sanctuary, where luxury meets entertainment in the heart of the c ...

    From $1156 per night (USD)

    VRBO

    Details
  • Chic 4-Bedroom Haven: Designer's Dream Home
    From $638 per night (USD)

    Expedia

    Chic 4-Bedroom Haven: Designer's Dream Home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Welcome to our Chic 4-Bedroom Haven in the heart of Ukrainian Village, Chicago! This meticulously curated home ...

    From $638 per night (USD)

    Expedia

    Details
  • Ideal South Loop 2BR w\/ Pool, Gym & Rooftop, nr L, by Blueground
    From $216 per night (USD)

    VRBO

    Ideal South Loop 2BR w\/ Pool, Gym & Rooftop, nr L, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Feel at home wherever you choose to live with Blueground. You’ll love this bright South Loop furnished two bedroom apart ...

    From $216 per night (USD)

    VRBO

    Details
  • Northbrook Rental
    From $504 per night (USD)

    VRBO

    Northbrook Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    1850 SF renovated unit is 22 minutes away from O’hare Airport & 25 min to downtown Chicago! This property has 3 bedrooms ...

    From $504 per night (USD)

    VRBO

    Details
  • Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground
    Click For Pricing

    VRBO

    Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...

    Click For Pricing

    VRBO

    Details
  • Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground
    From $218 per night (USD)

    Expedia

    Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the best of Chicago, with this two bedroom apartment in Lake View East. with balcony views over the city. It’ll ...

    From $218 per night (USD)

    Expedia

    Details