Chicago Rentals
From $367 per night (USD)VRBO
Kasa | Fresh & Bright 2 BD + Laptop Friendly | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $367 per night (USD)VRBO
From $309 per night (USD)VRBO
Kasa | Comfy Studio + Fast Wifi | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $309 per night (USD)VRBO
From $267 per night (USD)VRBO
Kasa | Inviting 1 BD + Pet Friendly | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $267 per night (USD)VRBO
From $173 per night (USD)Expedia
Spacious Loop 1BR w/ Pool, Gym, nr. the L & Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Chicago Loop furnished one bedroom a ...
From $173 per night (USD)Expedia
From $182 per night (USD)VRBO
Crisp Gold Coast 1BR nr. Mariano Park & Oak St. Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Gold Coast with views over the city. It’ll be easy to s ...
From $182 per night (USD)VRBO
From $531 per night (USD)VRBO
Kasa | Comfy 2 BD + Gym Access | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $531 per night (USD)VRBO
From $236 per night (USD)VRBO
The Upscale Getaway Near Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This cozy apartment features custom furniture in every room and a fireplace to warm up next to on a chilly night. Make u ...
From $236 per night (USD)VRBO
From $473 per night (USD)VRBO
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful bright & sunny Wicker Park 3 bedroom, 2 bath 1,500 square foot apartment located on the top floor of a private ...
From $473 per night (USD)VRBO
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Luxe West Loop Studio w/ Gym, Pool, Coworking, walk to UIC, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...
Click For PricingVRBO
From $411 per night (USD)Expedia
Luxe South Loop 2BR w/ Spa, Pool & Gym next to Grant Park, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this cozy two bedroom Blueground apartment. You’ll love coming hom ...
From $411 per night (USD)Expedia
From $133 per night (USD)VRBO
Modern Logan Square 1BR w/ Roof Deck & Gym, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Logan Square furnished one bedroom apar ...
From $133 per night (USD)VRBO
From $676 per night (USD)Expedia
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 22
Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost eve ...
From $676 per night (USD)Expedia
From $252 per night (USD)VRBO
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roscoe Village Inn offers charming vacation rental homes in Chicago's trendy Roscoe Village neighborhood 5 miles north o ...
From $252 per night (USD)VRBO
From $185 per night (USD)Expedia
Spacious Loop 2BR w/ Gym, Doorman, walk to L & Parks, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this charming Chicago Loop furnished two bedroom a ...
From $185 per night (USD)Expedia
From $159 per night (USD)VRBO
Retro Apartment in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to a colorful paradise in one of Andersonville's best-kept vintage buildings. Located on the ground floor, full o ...
From $159 per night (USD)VRBO
From $297 per night (USD)Expedia
Modern Wrigley Oasis with Parking!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully designed in the heart of Wrigley. Steps away from Wrigley Field, bars, restaurants and shops! This modern oa ...
From $297 per night (USD)Expedia
From $804 per night (USD)VRBO
2 Suites, 2 Floors in Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: You will get 2 separate Suites that are directly above one another. Each Suite has 2 bedrooms and 1 bathroom. T ...
From $804 per night (USD)VRBO
From $1486 per night (USD)VRBO
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME!!! ABSOLUTELY NO PARTIES OR LARGE GATHERINGS! We reserve the right t ask ...
From $1486 per night (USD)VRBO
From $227 per night (USD)VRBO
Premium Lakeview 2BR w/ Patio, W/D, walk to Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Lake View East with balcony views over the city. It’ll ...
From $227 per night (USD)VRBO
From $168 per night (USD)VRBO
Fun / Bright / Cubs Apt | Near Wrigley!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: A short 10 minute walk from Wrigley Field (0.8 miles) , and everything the popular Wrigleyville has to offer. ...
From $168 per night (USD)VRBO
From $180 per night (USD)VRBO
Hip River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Rush & Division furnished one bedroom ...
From $180 per night (USD)VRBO
From $208 per night (USD)Expedia
Sleek West Loop 1BR w/ Gym, Pool, near Fulton Market, 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 $208 per night (USD)Expedia
From $255 per night (USD)VRBO
Airy Loop 2BR w/ Pool, Gym, nr. Financial District & the L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Chicago Loop with balcony views over the city. It’ll be ...
From $255 per night (USD)VRBO
From $173 per night (USD)Expedia
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North furnished one bedroo ...
From $173 per night (USD)Expedia
From $96 per night (USD)VRBO
Premium Logan Square 1BR w/ Roof Deck & Gym, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this comfortable Logan Square furnished one bedroo ...
From $96 per night (USD)VRBO
From $167 per night (USD)Expedia
Cozy Loop 1BR w/ Pool, Gym, nr. Merchandise Mart & L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $167 per night (USD)Expedia
From $202 per night (USD)VRBO
Modern Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
From $202 per night (USD)VRBO
From $756 per night (USD)Expedia
Stylish 6 Bedroom Home in Trendy Logan Square!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Our stylish and newly-built home in Logan Square has all of the space a family or group of friends traveling together ne ...
From $756 per night (USD)Expedia
From $3547 per night (USD)VRBO
New Construction Building in River North!
- Bedrooms:
- 10
- Bathrooms:
- 11
- Sleeps:
- 16
Summary: This listing is perfect for your Chicago visit. You will get 4 brand new construction units (finished September ...
From $3547 per night (USD)VRBO
From $297 per night (USD)VRBO
A home away from home! <No events allowed>
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
vacation rental cleaning protocol Major surfaces are sanitized and disinfected. Major surfaces include countertops, ...
From $297 per night (USD)VRBO
From $483 per night (USD)VRBO
Magic Factory Loft 2West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Spacious Bright & Spotlessly Clean in the Heart of Everything Chicago - Chef Kitchen 3 bedrooms, 2 full baths Sleeps 8 g ...
From $483 per night (USD)VRBO
From $87 per night (USD)VRBO
Modern Coach House 2BR/1BA/Den in Hyde Park/ Kenwood, walk to U of C & Lakefront
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Kenwood Coach House| Rear Coach House Fully Furnished! Near U of C Hospital Hospital Staff/ Clinical Rotations REQUIRE ...
From $87 per night (USD)VRBO
From $103 per night (USD)VRBO
Mod Loop 1BR, w/ Gym, Pool nr the Millenium Park by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $103 per night (USD)VRBO
From $134 per night (USD)Expedia
Crisp Loop 1BR w/ Pool, Gym, nr. Theatre District & the 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 $134 per night (USD)Expedia
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Cozy Loop 2BR w/ Pool, Gym, nr. Financial District & L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this sophisticated two bedroom Blueground apartment. You’ll love c ...
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From $99 per night (USD)Expedia
Ideal River North 1BR w/pool, gym, nr. L & Magnificent Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $99 per night (USD)Expedia
From $242 per night (USD)VRBO
Crisp Loop 1BR w/ Pool, Gym, near Theatre District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $242 per night (USD)VRBO
From $237 per night (USD)Expedia
Hip Loop 1BR w/ Gym, Pool, W/D, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $237 per night (USD)Expedia
From $99 per night (USD)VRBO
Cozy West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $99 per night (USD)VRBO
From $138 per night (USD)Expedia
Hip River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Rush & Division furnished one bedroom ap ...
From $138 per night (USD)Expedia
From $163 per night (USD)VRBO
Bright Loop 1BR w/ Gym, Roofdeck, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $163 per night (USD)VRBO
From $172 per night (USD)Expedia
Smart Loop 1BR w/ Gym, Roofdeck, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this bright one bedroom Blueground apartment. You’ll love coming h ...
From $172 per night (USD)Expedia
From $169 per night (USD)VRBO
Modern River North 1BR w/ Gym + W/D near Mag Mile by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...
From $169 per night (USD)VRBO
From $264 per night (USD)Expedia
52nd Floor, VIEWS, Pool, Balcony, Pool, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Penthouses at Grand Plaza PH#10 Experience elevated city living from this stunning penthouse, soaring 52 st ...
From $264 per night (USD)Expedia
From $488 per night (USD)VRBO
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Walk to almost everything Chicago has to offer- Downtown, Mag Mile, North Ave beach, zoo, and Lincoln park, restaurants, ...
From $488 per night (USD)VRBO
From $802 per night (USD)Expedia
Magic Factory Loft 3East 4 Bd/4 Ba Families Groups
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Our bright spacious 4 bedroom sleeps up to 14 - 16 guests in super comfy Sealy Posturepedic beds. Bedroom 1 - Queen, 3 ...
From $802 per night (USD)Expedia
From $385 per night (USD)VRBO
#1816 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $385 per night (USD)VRBO
From $382 per night (USD)VRBO
#1805 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $382 per night (USD)VRBO
From $433 per night (USD)VRBO
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In the heart of Lakeview, still close to downtown, museums and McCormick Place. A quick stroll to Lake Michigan and the ...
From $433 per night (USD)VRBO
From $349 per night (USD)VRBO
Urban Luxury Home In Downtown Chicago!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Enjoy a stay at a world travelers' custom designed home! **PLEASE READ DESCRIPTION BELOW AND CONTACT US BEFORE REQUESTI ...
From $349 per night (USD)VRBO
From $595 per night (USD)VRBO
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 18
Most incredibly located, sun-filled home with designer kitchen, marble baths, and open-concept living areas—perfect for ...
From $595 per night (USD)VRBO
From $237 per night (USD)Expedia
Downtown Guild #4 | Mag Mile, Gold Coast, The Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $237 per night (USD)Expedia
From $330 per night (USD)VRBO
Downtown Urban Oasis! Near Transit, Sites, Nightlife -- Huge Deck + Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy a stay at a world travelers' Windy City home! **PLEASE READ FULL DESCRIPTION BELOW AND CONTACT US BEFORE REQUESTI ...
From $330 per night (USD)VRBO
From $354 per night (USD)Expedia
Guild #2 | Gold Coast Mag Mile Best Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐚𝐭 𝐨𝐮𝐫 𝐪𝐮 ...
From $354 per night (USD)Expedia
From $458 per night (USD)VRBO
Brilliant Downtown Chicago 3-Bedroom Condominium
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Situated in downtown Chicago, right next to the Godfrey Hotel, this spacious and bright 3-bedroom, 2-bathroom condominiu ...
From $458 per night (USD)VRBO
From $116 per night (USD)Expedia
Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Close to everything you will need for a convenient visit. There's a cozy little thai restaurant and bakery right on the ...
From $116 per night (USD)Expedia
From $631 per night (USD)VRBO
Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line and Wrigley
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 20
Lots of room for you to stretch out and enjoy the great location in East Lakeview. Nearby to public transportation incl ...
From $631 per night (USD)VRBO
From $379 per night (USD)VRBO
#2016 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $379 per night (USD)VRBO
From $377 per night (USD)VRBO
#1915 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $377 per night (USD)VRBO
From $374 per night (USD)VRBO
#1905 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $374 per night (USD)VRBO
From $396 per night (USD)VRBO
#1613 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $396 per night (USD)VRBO
From $772 per night (USD)VRBO
Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Our unique Lincoln Park Rowhouse is located in the heart of Lincoln Park and is perfect for your next group gathering in ...
From $772 per night (USD)VRBO
Click For PricingVRBO
Upscale Lakeview 2BR w/ W/D, patio, walk to Wrigley Field, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Lake View East. It’ll be easy to simply show up and sta ...
Click For PricingVRBO
From $776 per night (USD)Expedia
Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 23
Find us on Insta @bangtel for the best rates! Host the best Bachelorette party at ALOHA 2.0. If you you want to be in a ...
From $776 per night (USD)Expedia
From $572 per night (USD)VRBO
Southwestern Escape in Logan Square that sleeps 12 with grill and backyard patio
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Find us on Insta @bangtel for the best rates! Come feel the spirit of the Southwest in one of Chicago's best neighborho ...
From $572 per night (USD)VRBO
From $181 per night (USD)Expedia
Amazing Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
From $181 per night (USD)Expedia
From $233 per night (USD)VRBO
Beautiful Streeterville 1BR w/ Deck & Pool, walk to Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Streeterville furnished one bedroom apa ...
From $233 per night (USD)VRBO
From $243 per night (USD)Expedia
Deluxe Streeterville 1BR w/ Gym & Pool, close to Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $243 per night (USD)Expedia
From $1234 per night (USD)VRBO
Entire house 1 city block from Wrigley Field.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
We are very excited to prepare this amazing 2 story (with basement) home for your future stays. We are located in the he ...
From $1234 per night (USD)VRBO
From $92 per night (USD)Expedia
Dreamy Uptown 1BR w/ Gym, Rooftop Pool, 2 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Uptown. It’ll be easy to simply show up and start livin ...
From $92 per night (USD)Expedia
From $239 per night (USD)VRBO
Downtown Guild #3 | Mag Mile Gold Coast The Lake!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $239 per night (USD)VRBO
From $351 per night (USD)Expedia
Guild #1 | Gold Coast Mag Mile Best Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $351 per night (USD)Expedia
From $839 per night (USD)VRBO
Stunning Lincoln Park Single-Family House with Fantastic Game Room
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 14
Looking for a place for your group to gather together? This single-family home is perfect and private! Whip up meals in ...
From $839 per night (USD)VRBO
From $259 per night (USD)Expedia
Chic Loop 1BR w/ Pool & Dog Run, near Chicago Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Chicago Loop furnished one bedroom ap ...
From $259 per night (USD)Expedia
From $127 per night (USD)VRBO
Bright and Cozy 1BR Apartment in Logan Square!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our 1-bedroom/1 bath apartment is perfect for getaway to Chicago. We're located in the trendy Logan Square neighborhood. ...
From $127 per night (USD)VRBO
From $842 per night (USD)Expedia
Large 4BR/3BA • Safe Old Town Location • Walk Everywhere
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
🛏 Sleeping Arrangements, Plenty of room for everyone to have their own space! Bedroom 1: King bed Bedroom 2: Queen bed ...
From $842 per night (USD)Expedia
From $92 per night (USD)VRBO
Luxe West Loop Studio w/ Gym, Pool, Coworking, walk to UIC, 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 li ...
From $92 per night (USD)VRBO
From $315 per night (USD)VRBO
❤️ Spacious and Airy Apartment With Parking On Site!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $315 per night (USD)VRBO
From $100 per night (USD)VRBO
Bright Loop 1BR w/ Gym, Pool, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cheery one bedroom Blueground apartment. You’ll love coming h ...
From $100 per night (USD)VRBO
From $207 per night (USD)VRBO
Trendy 2BR Apartment in Logan Square!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Whatever brings you to town, our bright and airy two-bedroom apartment unit is complete with everything you need to feel ...
From $207 per night (USD)VRBO
From $206 per night (USD)VRBO
Stylish and Cute 2BR Apartment Near Wrigley!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Chicago! Our 2-bedroom/1 bathroom apartment unit is perfect for getaway to Chicago. Stretch out on a plush ...
From $206 per night (USD)VRBO
From $147 per night (USD)Expedia
Gorgeous Loop 1BR w/ Gym, Pool, near Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright Chicago Loop furnished one bedroom apa ...
From $147 per night (USD)Expedia
From $99 per night (USD)VRBO
Gorgeous Loop 1BR w/ Pool, Gym, nr. Financial District by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated West Loop furnished one bedroom ...
From $99 per night (USD)VRBO
From $156 per night (USD)Expedia
Ideal Loop 1BR w/ Roof deck & Gym, near Michigan Avenue, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Chicago Loop furnished one bedroom ...
From $156 per night (USD)Expedia
From $467 per night (USD)VRBO
Woodlawn Oasis...10 Minutes to Dining & Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Fun times with family and friends at this stylish beautiful home located 10 mins from Hyde Park, (Tiger Woods) Golf Cour ...
From $467 per night (USD)VRBO
From $1098 per night (USD)Expedia
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to the Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up ...
From $1098 per night (USD)Expedia
From $281 per night (USD)VRBO
Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Vil ...
From $281 per night (USD)VRBO
From $334 per night (USD)VRBO
Kasa | Bright & Airy 2 BD + Fast Wifi | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $334 per night (USD)VRBO
From $311 per night (USD)VRBO
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Penthouses at Grand Plaza PH#5 Experience elevated city living from this stunning penthouse, soaring 52 sto ...
From $311 per night (USD)VRBO
From $313 per night (USD)Expedia
53 Floor MagMile Penthouse Views, Balcony, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: The Penthouses at Grand Plaza PH#6 This 2-bedroom/2-bath soars 53 floors above Chicago, featuring dramatic livi ...
From $313 per night (USD)Expedia
From $404 per night (USD)VRBO
Historic 1920s Private Bungalow Near Logan Square!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Before every reservation this home is Professionally CLEANED and SANITIZED thoroughly from top to bottom. The only room ...
From $404 per night (USD)VRBO
From $225 per night (USD)Expedia
Luxurious 3Br with parking on premises 🌔
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This unique place has a style all its own. Modern/cozy feel. Freshly renovated. Enjoy the hassle-free parking on the pre ...
From $225 per night (USD)Expedia
From $132 per night (USD)VRBO
Modern Lakeview 1BR w/ Gym, Pool, 1 block to Lincoln Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Lake View East with high floor views over the city. It’ ...
From $132 per night (USD)VRBO
From $463 per night (USD)VRBO
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $463 per night (USD)VRBO
Click For PricingVRBO
Large 12 room house steps to Park, Shopping and Restaurants, 10 minutes to beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Large Jumbo Georgian two story brick house centrally located on the North side of Chicago in a quiet neighborhood with t ...
Click For PricingVRBO
From $340 per night (USD)VRBO
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: Why pay $$$ Chi parking when you have a 2 CAR GARAGE DOWNTOWN? Our 4br/3.5ba rowhome has 4 levels & 2 ROOFTOPS; ...
From $340 per night (USD)VRBO
From $164 per night (USD)VRBO
Bright/Cozy/Hip 2/1 Apt | Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Enjoy Chicago as a Chicagoan and welcome to the historic now hip neighborhood of Logan Square. It is a must see ...
From $164 per night (USD)VRBO
From $347 per night (USD)Expedia
Chicago Riverhouse with private fenced in oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the ...
From $347 per night (USD)Expedia
From $144 per night (USD)VRBO
Mod River North 1BR w/ Gym, Pool, near L stop & Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near North with views over the city. It’ll be easy to s ...
From $144 per night (USD)VRBO
From $138 per night (USD)Expedia
Trendy River North 1BR w/ Gym, Pool, near L stop & Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $138 per night (USD)Expedia