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  • Urban Oasis - Chic Design - Game room\/Movie room
    From $431 per night (USD)

    VRBO

    Urban Oasis - Chic Design - Game room\/Movie room

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Located in a quiet and safe neighborhood, our property offers a unique blend of style, comfort, and entertainment. Step ...

    From $431 per night (USD)

    VRBO

    Details
  • Exquisite West Loop Jr 1BR w\/ Gym & Rooftop, nr Union Park, by Blueground
    From $163 per night (USD)

    Expedia

    Exquisite West Loop Jr 1BR w\/ Gym & Rooftop, nr Union Park, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in West Loop. . It’ll be easy to simply show up and start ...

    From $163 per night (USD)

    Expedia

    Details
  • Navy Blues 2BR\/2bath quintessential , private condo.
    From $191 per night (USD)

    VRBO

    Navy Blues 2BR\/2bath quintessential , private condo.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Private 2 be/2 bath condo located in heart of Chicago Ridge. Whether it’s a work trip, family vacation or a visiting fam ...

    From $191 per night (USD)

    VRBO

    Details
  • Spacious Inverness Home ~ 36 Mi to Chicago!
    From $572 per night (USD)

    Expedia

    Spacious Inverness Home ~ 36 Mi to Chicago!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Unwind in elegance with your whole family at this 4-bedroom, 4.5-bath vacation rental in Inverness, IL! This stunning pr ...

    From $572 per night (USD)

    Expedia

    Details
  • Bucktown Apartment near all amazing restaurants, shops and bar\/lounges
    From $200 per night (USD)

    VRBO

    Bucktown Apartment near all amazing restaurants, shops and bar\/lounges

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Recently renovated apartment in a two-story building. Sits right above our family-owned and operated chicken restaurant. ...

    From $200 per night (USD)

    VRBO

    Details
  • The Banksy 4bd Duplex - King bed - walk to United Center, close to downtown
    From $536 per night (USD)

    Expedia

    The Banksy 4bd Duplex - King bed - walk to United Center, close to downtown

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    United Center Greystone, modern 4 bedroom, 1 king bed, 3 queen , 2 bath 2 level duplex apartment with awesome outdoor li ...

    From $536 per night (USD)

    Expedia

    Details
  • Spacious 2BR, this hidden gem combines vintage allure with urban flair!
    From $130 per night (USD)

    VRBO

    Spacious 2BR, this hidden gem combines vintage allure with urban flair!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the charm of The Maestro, an amazing 2-bedroom, 1-bath apartment nestled within a stunning 1920’s era Chicago b ...

    From $130 per night (USD)

    VRBO

    Details
  • Luxe living awaits in our newly built condo in the artsy Bronzeville district
    From $350 per night (USD)

    Expedia

    Luxe living awaits in our newly built condo in the artsy Bronzeville district

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Step into luxury with our newly constructed, entire condo located in the heart of the vibrant Bronzeville Art District. ...

    From $350 per night (USD)

    Expedia

    Details
  • Chic 2BR Haven: Minutes from Downtown & Medical District
    From $96 per night (USD)

    VRBO

    Chic 2BR Haven: Minutes from Downtown & Medical District

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Welcome to your tranquil urban oasis in the vibrant heart of Chicago, IL! Nestled on a serene block near Douglas Park in ...

    From $96 per night (USD)

    VRBO

    Details
  • Classic West Loop 1BR w\/ Gym, near Fulton Market & I-90, by Blueground
    From $180 per night (USD)

    Expedia

    Classic West Loop 1BR w\/ Gym, near Fulton Market & I-90, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $180 per night (USD)

    Expedia

    Details
  • Chicago Big House Central
    From $352 per night (USD)

    VRBO

    Chicago Big House Central

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    12

    This listing is NOT new, although the rental platforms may show it new. This "whole house" rental is a combination of tw ...

    From $352 per night (USD)

    VRBO

    Details
  • Villa Noir Chicago Victorian home 7 min to downtown, museums, shops & the beach
    From $550 per night (USD)

    Expedia

    Villa Noir Chicago Victorian home 7 min to downtown, museums, shops & the beach

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to Villa Noir - an expertly designed vacation HOME fully equipped with everything you need for a most enjoyable ...

    From $550 per night (USD)

    Expedia

    Details
  • Trendy River North 1BR w\/ Pool & Gym, near Riverwalk, by Blueground
    From $99 per night (USD)

    VRBO

    Trendy River North 1BR w\/ Pool & Gym, near Riverwalk, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in River North. . It’ll be easy to simply show up and star ...

    From $99 per night (USD)

    VRBO

    Details
  • Lux\/Clean\/Ideal Comfy\/Vibe\/King BED &Free Parking
    From $198 per night (USD)

    Expedia

    Lux\/Clean\/Ideal Comfy\/Vibe\/King BED &Free Parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Dreamsicle Lux Vibe is great for couples, friend adventurers, family fun time, and business travelers. Experience the co ...

    From $198 per night (USD)

    Expedia

    Details
  • 7B\/3BA Private Unit in Lincoln Park near Wrigley
    From $1202 per night (USD)

    VRBO

    7B\/3BA Private Unit in Lincoln Park near Wrigley

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    14

    Summary: Discover the vibrant heart of Chicago from our Amazing Fully Furnished 7BR Home. Located in the city's most pop ...

    From $1202 per night (USD)

    VRBO

    Details
  • Luxury Chic Condo Near Hot Attractions w\/FastWi-Fi
    From $244 per night (USD)

    Expedia

    Luxury Chic Condo Near Hot Attractions w\/FastWi-Fi

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Escape to this spacious "Home Away from Home" fully equipped with all you need for your comfort & enjoyment. Each of th ...

    From $244 per night (USD)

    Expedia

    Details
  • Lovely Oak Park Boho Vintage 3bd\/1ba. Located near public transit\/free parking
    From $325 per night (USD)

    VRBO

    Lovely Oak Park Boho Vintage 3bd\/1ba. Located near public transit\/free parking

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Gorgeous 3BR 1BA apt near downtown Oak Park & 10 mins from the Medical District, Pilsen & West Loop Chicago! Get the bes ...

    From $325 per night (USD)

    VRBO

    Details
  • 2 bedroom Pastel Loft 1 mi from the Chicago Lakefront, close to CTA transit!
    From $288 per night (USD)

    Expedia

    2 bedroom Pastel Loft 1 mi from the Chicago Lakefront, close to CTA transit!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Welcome to our chic and colorful lofted apartment in the lovely neighborhood of Roger’s Park in Chicago! It's convenient ...

    From $288 per night (USD)

    Expedia

    Details
  • Cozy Home Inn Glenview
    From $200 per night (USD)

    VRBO

    Cozy Home Inn Glenview

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    This home is located in beautiful Glenview area. Large backyard, 1 car garage and a drive way that can accommodate up t ...

    From $200 per night (USD)

    VRBO

    Details
  • Trendy Two Bedroom Unit-15mins to downtown!
    From $135 per night (USD)

    Expedia

    Trendy Two Bedroom Unit-15mins to downtown!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Trendy two unit apartment nested between South Loop and Bronzeville. The unit is in close proximity to McCormick,Winturs ...

    From $135 per night (USD)

    Expedia

    Details
  • Luxury Loft Collection 903 - Terrace - River North
    From $1019 per night (USD)

    VRBO

    Luxury Loft Collection 903 - Terrace - River North

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    16

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

    From $1019 per night (USD)

    VRBO

    Details
  • Luxury Loft Collection 902 - Terrace - River North
    From $988 per night (USD)

    Expedia

    Luxury Loft Collection 902 - Terrace - River North

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    16

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

    From $988 per night (USD)

    Expedia

    Details
  • Deluxe West Loop 1BR w\/ Rooftop, Gym & Grills, nr Park, by Blueground
    From $149 per night (USD)

    VRBO

    Deluxe West Loop 1BR w\/ Rooftop, Gym & Grills, nr Park, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $149 per night (USD)

    VRBO

    Details
  • Ideal West Loop Jr 1BR w\/ Rooftop, Gym & Grills, nr Park, by Blueground
    From $130 per night (USD)

    Expedia

    Ideal West Loop Jr 1BR w\/ Rooftop, Gym & Grills, nr Park, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $130 per night (USD)

    Expedia

    Details
  • Delightful West Loop 1BR w\/ Gym, near Fulton Market & I-90, by Blueground
    From $146 per night (USD)

    VRBO

    Delightful West Loop 1BR w\/ Gym, near Fulton Market & I-90, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in West Loop. . It’ll be easy to simply show up and start ...

    From $146 per night (USD)

    VRBO

    Details
  • Cozy 2 Bedroom unit
    From $120 per night (USD)

    Expedia

    Cozy 2 Bedroom unit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Trendy two unit apartment nested between South Loop and Bronzeville. The unit is in close proximity to McCormick,Winturs ...

    From $120 per night (USD)

    Expedia

    Details
  • Lovely vintage Oak Park 3bd 1ba perfectly located Chicago loop & public transit
    From $192 per night (USD)

    VRBO

    Lovely vintage Oak Park 3bd 1ba perfectly located Chicago loop & public transit

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Gorgeous 3BR 1BA apt near downtown Oak Park & 15 mins from the Medical District, Pilsen & Downtown Chicago! Get the best ...

    From $192 per night (USD)

    VRBO

    Details
  • Chicago Vacation Rental, 19 Mi to Downtown Area!
    From $122 per night (USD)

    Expedia

    Chicago Vacation Rental, 19 Mi to Downtown Area!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Explore the vibrant city of Chicago from the comfort of this 4-bedroom, 2-bath vacation rental. Located just minutes awa ...

    From $122 per night (USD)

    Expedia

    Details
  • Des Plaines Urban Retreat near Ohare, Mall, Casino
    From $224 per night (USD)

    VRBO

    Des Plaines Urban Retreat near Ohare, Mall, Casino

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Escape to our cozy 3-bedroom, 1.5-bathroom newly remodeled retreat in Des Plaines! Comfortable and tastefully decorate ...

    From $224 per night (USD)

    VRBO

    Details
  • McCormick 3B\/2Ba Family Oasis up to 8 guests with Parking-Optional\/Gym\/Patio
    From $787 per night (USD)

    Expedia

    McCormick 3B\/2Ba Family Oasis up to 8 guests with Parking-Optional\/Gym\/Patio

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    • Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...

    From $787 per night (USD)

    Expedia

    Details
  • Luxurious apartment McCormick Place 5 King bedrooms\/3bath Suite for groups
    From $1598 per night (USD)

    VRBO

    Luxurious apartment McCormick Place 5 King bedrooms\/3bath Suite for groups

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    • Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 1800 sq f Luxurious ...

    From $1598 per night (USD)

    VRBO

    Details
  • McCormick Patio skyline view 2b\/2b with optional Parking\/sleep 6
    From $561 per night (USD)

    Expedia

    McCormick Patio skyline view 2b\/2b with optional Parking\/sleep 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    • Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Private patio • Cit ...

    From $561 per night (USD)

    Expedia

    Details
  • Luxurious McCormick 3be\/2ba Suite\/up to 8 guests w optional parking\/Gym\/Patio
    From $715 per night (USD)

    VRBO

    Luxurious McCormick 3be\/2ba Suite\/up to 8 guests w optional parking\/Gym\/Patio

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    • Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 KING size bedroo ...

    From $715 per night (USD)

    VRBO

    Details
  • Luxurious McCormick 6 bed\/4 bath Suite for up to 12 guests w Jacuzzi\/Opt parking
    From $1458 per night (USD)

    Expedia

    Luxurious McCormick 6 bed\/4 bath Suite for up to 12 guests w Jacuzzi\/Opt parking

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    • Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Jacuzzi in the unit • 2609 sq f Luxurious unit ...

    From $1458 per night (USD)

    Expedia

    Details
  • Luxurious McCormick 5 bed\/4 bath Suite for up to 12 guests with optional parking
    From $1636 per night (USD)

    VRBO

    Luxurious McCormick 5 bed\/4 bath Suite for up to 12 guests with optional parking

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    • Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Luxurious unit for ...

    From $1636 per night (USD)

    VRBO

    Details
  • McCormick Place 6 twin beds + Sofa bed with Optional parking for up to 8 guests
    From $684 per night (USD)

    Expedia

    McCormick Place 6 twin beds + Sofa bed with Optional parking for up to 8 guests

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    • Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 6 twin size beds + ...

    From $684 per night (USD)

    Expedia

    Details
  • South Shore Retreat 5 bedrooms\/entertainment
    From $233 per night (USD)

    VRBO

    South Shore Retreat 5 bedrooms\/entertainment

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    This stylish place to stay is perfect for group or work trips. Enjoy a five minute stroll to Lake Michigan or drive five ...

    From $233 per night (USD)

    VRBO

    Details
  • Divine West Loop 1BR w\/ Gym & Rooftop, nr Union Park, by Blueground
    From $101 per night (USD)

    Expedia

    Divine West Loop 1BR w\/ Gym & Rooftop, nr Union Park, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $101 per night (USD)

    Expedia

    Details
  • Dreamy West Loop 1BR w\/ Rooftop & Dog Wash, nr L, by Blueground
    From $183 per night (USD)

    VRBO

    Dreamy West Loop 1BR w\/ Rooftop & Dog Wash, nr L, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in West Loop. . It’ll be easy to simply show up and start ...

    From $183 per night (USD)

    VRBO

    Details
  • Chicago New 2BR Home w 3 Beds and HighSpeed Internet
    From $355 per night (USD)

    Expedia

    Chicago New 2BR Home w 3 Beds and HighSpeed Internet

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Enjoy a stylish experience at this centrally-located home in the eccentric Wicker Park neighborhood of Chicago. ...

    From $355 per night (USD)

    Expedia

    Details
  • Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop,  2car Garage
    From $650 per night (USD)

    VRBO

    Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    16

    Luxurious Modern Retreat with 1000 sqft Rooftop Welcome to the Monticello - our stunning modern new construction, desig ...

    From $650 per night (USD)

    VRBO

    Details
  • Downtown Delight: Chic Stay near Chicago Theater! Pets are welcome!
    From $298 per night (USD)

    Expedia

    Downtown Delight: Chic Stay near Chicago Theater! Pets are welcome!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Each elegantly designed room at the hotel comes with plush bedding and modern amenities to ensure a comfortable experien ...

    From $298 per night (USD)

    Expedia

    Details
  • Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
    From $543 per night (USD)

    VRBO

    Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Bee's Knees - a blast from the past with a hollywood-glam twist. This 4 BR home is the perfect getaway for a ...

    From $543 per night (USD)

    VRBO

    Details
  • Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly
    From $178 per night (USD)

    Expedia

    Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Each elegantly designed room at the hotel comes with plush bedding and modern amenities to ensure a comfortable experien ...

    From $178 per night (USD)

    Expedia

    Details
  • Tranquil 1BR Urban Retreat in Hyde Park
    From $75 per night (USD)

    VRBO

    Tranquil 1BR Urban Retreat in Hyde Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to a cozy urban retreat in the heart of Chicago! Our fully furnished 1-bedroom apartment offers a stylish and co ...

    From $75 per night (USD)

    VRBO

    Details
  • Inviting Studio Apartment in Evanston
    From $65 per night (USD)

    Expedia

    Inviting Studio Apartment in Evanston

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Escape to our inviting studio nestled in the vibrant heart of Evanston. Perfect for solo travelers or couples seeking a ...

    From $65 per night (USD)

    Expedia

    Details
  • Lovely Home 10 minutes from O'Hare Airport - Entire main floor
    From $275 per night (USD)

    VRBO

    Lovely Home 10 minutes from O'Hare Airport - Entire main floor

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    It is a lovely spacious and cozy home nestled in a peaceful neighborhood. We are not a five-star hotel but we sure are a ...

    From $275 per night (USD)

    VRBO

    Details
  • Cozy Spacious 3br
    From $153 per night (USD)

    Expedia

    Cozy Spacious 3br

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Nice and Spacious Cozy apartment nestled in the heart of chicago, top floor apt. With Double ovens when cooking for a ni ...

    From $153 per night (USD)

    Expedia

    Details
  • New home w\/view & party deck - 2nd Floor
    From $800 per night (USD)

    VRBO

    New home w\/view & party deck - 2nd Floor

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Prime Location: Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovat ...

    From $800 per night (USD)

    VRBO

    Details
  • Majestic King| Shops|Backyard
    From $292 per night (USD)

    Expedia

    Majestic King| Shops|Backyard

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Discover comfort and convenience in this stunning modern farmhouse. Nestled within, you'll encounter a luxurious king be ...

    From $292 per night (USD)

    Expedia

    Details
  • Beautiful Suburban Home 30 minutes from downtown Chicago!
    From $250 per night (USD)

    VRBO

    Beautiful Suburban Home 30 minutes from downtown Chicago!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Alone, with friends, or with family? Whatever your needs, this house is sure to fulfill your expectations. Full house in ...

    From $250 per night (USD)

    VRBO

    Details
  • Newly renovated 2 bedroom Garden apartment, Living room, bath,and full kitchen.
    From $175 per night (USD)

    Expedia

    Newly renovated 2 bedroom Garden apartment, Living room, bath,and full kitchen.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Keep it simple at this peaceful and centrally-located place to almost Everything. Newly renovated 3 bedroom apartment, o ...

    From $175 per night (USD)

    Expedia

    Details
  • Newly remodeled, 3 bedroom apartment 20 min from almost everything in the city
    From $230 per night (USD)

    VRBO

    Newly remodeled, 3 bedroom apartment 20 min from almost everything in the city

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Keep it simple at this peaceful and centrally-located place to almost Everything. Newly renovated 3 bedroom apartment, o ...

    From $230 per night (USD)

    VRBO

    Details
  • Opulence in Oak Park
    From $212 per night (USD)

    Expedia

    Opulence in Oak Park

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our newly remodeled, luxurious 4-bedroom, 2-bathroom retreat in Oak Park, IL. This opulent haven boasts elega ...

    From $212 per night (USD)

    Expedia

    Details
  • Modern Bungalow near the beach! 20 minutes to downtown!
    From $280 per night (USD)

    VRBO

    Modern Bungalow near the beach! 20 minutes to downtown!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    This stylish home is perfect for group trips. With only 26 minutes to Midway airport and less than 10 minutes to the nea ...

    From $280 per night (USD)

    VRBO

    Details
  • Cozy Basement with its own private entrance. 2 bedrooms and 1 full bath.
    From $125 per night (USD)

    Expedia

    Cozy Basement with its own private entrance. 2 bedrooms and 1 full bath.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This basement has its own private electronic keyless entry. It features 2 bedrooms, 1 full bath. Master bedroom has a w ...

    From $125 per night (USD)

    Expedia

    Details
  • 3 Bed Wrigley home w\/view & party deck - 3rd Fl
    From $800 per night (USD)

    VRBO

    3 Bed Wrigley home w\/view & party deck - 3rd Fl

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovated down to the s ...

    From $800 per night (USD)

    VRBO

    Details
  • Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by RedAwning
    From $422 per night (USD)

    Expedia

    Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by RedAwning

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined stre ...

    From $422 per night (USD)

    Expedia

    Details
  • ❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square
    From $378 per night (USD)

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $378 per night (USD)

    VRBO

    Details
  • Modern, Cozy & Chic 2 BR\/1BA Apartment in Lincoln Square\/Ravenswood, Chicago, IL
    From $188 per night (USD)

    VRBO

    Modern, Cozy & Chic 2 BR\/1BA Apartment in Lincoln Square\/Ravenswood, Chicago, IL

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our newly renovated apartment in the heart of Lincoln Square! This modern, cozy space features 2 bedrooms w/ ...

    From $188 per night (USD)

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    Details
  • Bright 3BR\/1BA FREE Parking\/Laundry in Pilsen. Minutes from Downtown
    From $180 per night (USD)

    VRBO

    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 $180 per night (USD)

    VRBO

    Details
  • Perfect 2BD\/1BA FREE Garage Parking\/Laundry in Pilsen. Minutes to downtown.
    From $100 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 $100 per night (USD)

    VRBO

    Details
  • Quiet cozy home close to amenities
    From $51 per night (USD)

    VRBO

    Quiet cozy home close to amenities

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Relaxing overnight stay no fuss! Walking distance to forest reserve suitable for hiking or just going for a walk. Nice p ...

    From $51 per night (USD)

    VRBO

    Details
  • Windy City Welcome
    From $348 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 $348 per night (USD)

    VRBO

    Details
  • Landing at NEXT - 1 Bedroom in Near North Side
    From $140 per night (USD)

    VRBO

    Landing at NEXT - 1 Bedroom in Near North Side

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to the NEXT evolution of luxury living. Our apartments come in varied layouts outfitted with contemporary featur ...

    From $140 per night (USD)

    VRBO

    Details
  • Chic River North Condo 2BR 2BA with Private Balcony
    From $371 per night (USD)

    VRBO

    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 $371 per night (USD)

    VRBO

    Details
  • A Home Away From Home!
    From $270 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 $270 per night (USD)

    VRBO

    Details
  • River North Central Home With Balcony
    From $305 per night (USD)

    VRBO

    River North Central Home With Balcony

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Summary: Enjoy a stylish experience at this centrally-located home in Chicago's River West neighborhood. Relax indoors a ...

    From $305 per night (USD)

    VRBO

    Details
  • Fulton market \/ Noble Square FREE parking, Laundry, 2.5 miles to Mag Mile!
    From $299 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 $299 per night (USD)

    VRBO

    Details
  • Unique Chicago Penthouse Loft - Amazing Deal & Location
    From $304 per night (USD)

    VRBO

    Unique Chicago Penthouse Loft - Amazing Deal & Location

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Ideal for a Chicago Get-Away, business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (no ...

    From $304 per night (USD)

    VRBO

    Details
  • Inactive listing
    From $360 per night (USD)

    VRBO

    Inactive listing

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Delete this account no longer listing this unitaahdjdjdhdbrhdjdntnrgwgdhfjfkrjebdhehehdbfjfheheerehdbdbdvdjfkgjdbdvdhfjt ...

    From $360 per night (USD)

    VRBO

    Details
  • Lincolnwood Rental\n
    Click For Pricing

    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 ...

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    Details
  • Palos Hills Rental
    From $433 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 $433 per night (USD)

    VRBO

    Details
  • Summit Rental
    From $432 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 $432 per night (USD)

    VRBO

    Details
  • Arlington Heights Rental
    From $435 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 $435 per night (USD)

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    Details
  • Elgin Rental- Jay St\n
    From $454 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 $454 per night (USD)

    VRBO

    Details
  • Modern 2BR Furnished Apt w\/In-Unit Laundry!
    From $97 per night (USD)

    VRBO

    Modern 2BR Furnished Apt w\/In-Unit Laundry!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your perfect retreat nestled in the heart of Chicago. Our fully furnished 2-bedroom apartment is a stylish fu ...

    From $97 per night (USD)

    VRBO

    Details
  • Chicago Rental - Vernon Ave
    From $229 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 $229 per night (USD)

    VRBO

    Details
  • Berwyn Rental
    From $364 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 $364 per night (USD)

    VRBO

    Details
  • Pearly Gates w\/ 2-Car Garage
    From $236 per night (USD)

    VRBO

    Pearly Gates w\/ 2-Car Garage

    Bedrooms:
    1
    Bathrooms:
    3
    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 $236 per night (USD)

    VRBO

    Details
  • Beautiful 2 bedroom 2 bathroom condo
    Click For Pricing

    VRBO

    Beautiful 2 bedroom 2 bathroom condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This 2 bedroom 2 bathroom condo is perfect for your Chicago stay. We offer all your essentials such as; toiletries, dish ...

    Click For Pricing

    VRBO

    Details
  • Hoffman Estates Rental
    From $399 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 $399 per night (USD)

    VRBO

    Details
  • Des Plaines Rental
    From $341 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 $341 per night (USD)

    VRBO

    Details
  • Elk Grove Village Rental - Kingsbridge Rd
    From $399 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 $399 per night (USD)

    VRBO

    Details
  • Orland Park Rental -Huntington Ct
    From $399 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 $399 per night (USD)

    VRBO

    Details
  • Elk Grove Village Rental
    From $399 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 $399 per night (USD)

    VRBO

    Details
  • Spacious 3BR Apt w\/ In-Unit Laundry
    From $94 per night (USD)

    VRBO

    Spacious 3BR Apt w\/ In-Unit Laundry

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $94 per night (USD)

    VRBO

    Details
  • Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville
    From $200 per night (USD)

    Expedia

    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 $200 per night (USD)

    Expedia

    Details
  • Family union get together
    From $316 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 $316 per night (USD)

    VRBO

    Details
  • Stunning Suite 2 @ Hotel Nemo Downtown
    From $105 per night (USD)

    VRBO

    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 $105 per night (USD)

    VRBO

    Details
  • Gold Coast Luxury Condo w\/ Rooftop Pool
    From $267 per night (USD)

    VRBO

    Gold Coast Luxury Condo w\/ Rooftop Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Summary: Enjoy a stylish experience at this centrally-located place.Located in the heart of Gold Coast, Chicago's most s ...

    From $267 per night (USD)

    VRBO

    Details
  • Chicago  Rental - Narragansett
    From $290 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 $290 per night (USD)

    VRBO

    Details
  • Chic Retreat Steps from University of Chicago
    From $65 per night (USD)

    VRBO

    Chic Retreat Steps from University of Chicago

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Discover the ultimate urban haven at 5461 S Drexel Ave in Hyde Park a true gem that beckons to both industrious professi ...

    From $65 per night (USD)

    VRBO

    Details
  • Cozy Well Maintained Bronzeville 2 Bed 1 bath Condo! 5 min to U of C
    From $108 per night (USD)

    VRBO

    Cozy Well Maintained Bronzeville 2 Bed 1 bath Condo! 5 min to U of C

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Quiet & Cozy Condo in Bronzeville. Updated with all new stainless steel appliances, this is the perfect getaway. This pr ...

    From $108 per night (USD)

    VRBO

    Details
  • The Grand Kimball Lodge, Logan Square, Sleeps 14
    From $1423 per night (USD)

    VRBO

    The Grand Kimball Lodge, Logan Square, Sleeps 14

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    The Grand Kimball Lodge is filled with enormous windows, a large, open concept layout, and Wes Anderson inspired decor. ...

    From $1423 per night (USD)

    VRBO

    Details
  • Chicago Rental - W 64th St
    From $278 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 $278 per night (USD)

    VRBO

    Details
  • Spacious, Clean and Steps from Wrigley Field!
    From $294 per night (USD)

    VRBO

    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 $294 per night (USD)

    VRBO

    Details
  • South Shore Home Near Lake for long-term stays, corporate travelers, and nurses
    From $135 per night (USD)

    Expedia

    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 $135 per night (USD)

    Expedia

    Details
  • Chicago Rental - W Berwyn Ave\n
    From $290 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 $290 per night (USD)

    VRBO

    Details
  • Chic 4-Bedroom Haven: Designer's Dream Home
    From $403 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 $403 per night (USD)

    Expedia

    Details