Chicago Rentals
From $305 per night (USD)VRBO
51st Floor MagMile Penthouse Views Balcony Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Penthouses at Grand Plaza PH#7 Experience elevated city living from this stunning penthouse, soaring 52 sto ...
From $305 per night (USD)VRBO
From $324 per night (USD)VRBO
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple dir ...
From $324 per night (USD)VRBO
From $169 per night (USD)VRBO
Roomy South Loop 1BR w/ Pool, Lounge, walk to CTA Trains, 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 $169 per night (USD)VRBO
From $170 per night (USD)Expedia
Airy South Loop 1BR w/ Lounge, Pool & Gym near Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop with balcony views over the city. It’ll be e ...
From $170 per night (USD)Expedia
From $138 per night (USD)VRBO
Bright South Loop 1BR w/ Pool, Gym, walk to Museum Campus, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Central Station with views over the city. It’ll be easy ...
From $138 per night (USD)VRBO
From $382 per night (USD)VRBO
#2003 - 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 $233 per night (USD)VRBO
Best Location! Luxury 51st FL Amazing Views of Lake & City, Hotel-like Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
51st Floor! Best Value in Chicago! Luxe condo in a FANTASTIC location! Perfect for vacation, short-term housing or cor ...
From $233 per night (USD)VRBO
From $96 per night (USD)Expedia
Fantastic River North 1BR w/ Gym, Rooftop, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in River North with views over the city. It’ll be easy to ...
From $96 per night (USD)Expedia
From $870 per night (USD)VRBO
Stunning Designer Loft in Fulton Market, Sleeps 24 | Featured In Architectural D
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 24
Summary: 2 beautiful side-by-side apartments comprising 5,000 square feet (the entire 2nd floor) of a brick-and-timber l ...
From $870 per night (USD)VRBO
From $293 per night (USD)VRBO
#1516 - 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 $293 per night (USD)VRBO
From $401 per night (USD)VRBO
#1902 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $401 per night (USD)VRBO
From $408 per night (USD)VRBO
#1401 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $408 per night (USD)VRBO
From $311 per night (USD)VRBO
#1515 - 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 $311 per night (USD)VRBO
From $326 per night (USD)VRBO
Modern 4 Bedroom Apt Next to Park&Pool | Lakeview
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Ready to stay in MODERN Chicago? Our NEWLY FINISHED 2-level masterpiece has IMPECCABLE DESIGN, 4 bedrooms, IN-U ...
From $326 per night (USD)VRBO
From $755 per night (USD)VRBO
MAG MILE MEGA Entire Floor 4BD 4BA +Rooftop&Gym
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome! You've found a hidden gem in the Gold Coast / Streeterville neighborhood: Guests love our home because: - You ...
From $755 per night (USD)VRBO
From $639 per night (USD)Expedia
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertai ...
From $639 per night (USD)Expedia
From $163 per night (USD)VRBO
Roomy Ravenswood 2BR w/ Rooftop, BBQ, next to Brown line, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this cozy North Center furnished two bedroom apart ...
From $163 per night (USD)VRBO
From $148 per night (USD)Expedia
Modern South Loop 1BR w/ Pool + Gym, walk to Soldier Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Central Station furnished one bedroom ...
From $148 per night (USD)Expedia
From $273 per night (USD)VRBO
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
1700 sqft penthouse in the historic west end of the West Loop. Nestled on a quiet street, minutes away from incredible r ...
From $273 per night (USD)VRBO
From $432 per night (USD)Expedia
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Meet NEW and CHARM with exposed brick, dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, ope ...
From $432 per night (USD)Expedia
From $531 per night (USD)VRBO
Lincoln Park Charm Near Everything + On site Parking Spot Included
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come stay at this gorgeous, clean, renovated, top-floor apartment in beautiful Lincoln Park. The unit is located on a qu ...
From $531 per night (USD)VRBO
From $455 per night (USD)Expedia
1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Beautiful and newly furnished condo in the heart of Chicago Chinatown area with 4 bedrooms, 2 baths, two separate living ...
From $455 per night (USD)Expedia
From $97 per night (USD)VRBO
Lovely River North 1BR w/ Gym, Pool, near L stop & Beach, 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 $97 per night (USD)VRBO
From $134 per night (USD)Expedia
Darling 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 $134 per night (USD)Expedia
From $1941 per night (USD)VRBO
Luxurious Four-Level Home with Personal Touches Everywhere
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 17
Cook in a dream kitchen with top-of-the-line appliances at this sprawling and luxurious home located on a quiet, one-way ...
From $1941 per night (USD)VRBO
From $313 per night (USD)Expedia
Walking distance to restaurants, shops and Lake Michigan,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Residence on the Avenue. A Spacious 1700 sq.ft. condo in a stunning blonde brick/limestone 1928 building on a tree lined ...
From $313 per night (USD)Expedia
From $116 per night (USD)VRBO
Sleek 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 spacious one bedroom Blueground apartment. You’ll love coming ...
From $116 per night (USD)VRBO
From $170 per night (USD)Expedia
Smart 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 $170 per night (USD)Expedia
From $88 per night (USD)VRBO
Elegant Lakeview 1BR w/ Gym, Pool, 1 block to Lincoln Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Lake View East furnished one be ...
From $88 per night (USD)VRBO
From $425 per night (USD)VRBO
#1501 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $425 per night (USD)VRBO
From $485 per night (USD)VRBO
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Stunning 2,500 square foot brick-and-timber luxury loft with 15 foot ceilings located in the heart of the vibra ...
From $485 per night (USD)VRBO
From $380 per night (USD)VRBO
#1916 - 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 $380 per night (USD)VRBO
From $141 per night (USD)VRBO
Spacious 3 bdrm 1.5 bath; Renovated Woodlawn; Incredible Access; UChicago; OPC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This large commodious home is the ultimate place to relax, visit and/or collaborate in our beautiful city. Near the site ...
From $141 per night (USD)VRBO
From $315 per night (USD)Expedia
Trendy West Town Flat - 2 bed / 1.5 bath with parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Find your wanderlust in this perfectly located West Town condo. Situated between Chicago’s West Loop and Wicker Park ne ...
From $315 per night (USD)Expedia
From $569 per night (USD)VRBO
The Greenleaf House—Whole House
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 12
The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gat ...
From $569 per night (USD)VRBO
From $446 per night (USD)VRBO
Beautiful Corner 2 Bedroom 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 $446 per night (USD)VRBO
From $371 per night (USD)VRBO
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*Please inquire before requesting to book* 4 bedroom 2 bath apartment. In the Historic up and coming kenwood neighbor ...
From $371 per night (USD)VRBO
From $258 per night (USD)Expedia
Airy Lakeview 1BR w/ W/D, 1 block to L, near Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Lake View East furnished one bedroom a ...
From $258 per night (USD)Expedia
From $372 per night (USD)VRBO
#1812 - 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 $372 per night (USD)VRBO
From $415 per night (USD)VRBO
#1402 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $415 per night (USD)VRBO
From $467 per night (USD)VRBO
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 20
Beautiful and newly furnished condo in the heart of Chicago Chinatown area with 4 bedrooms, 2 baths, a spacious living r ...
From $467 per night (USD)VRBO
From $675 per night (USD)VRBO
3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Live like a local in one of Chicago’s best neighborhoods! Located in a family-owned boutique building in the vibrant and ...
From $675 per night (USD)VRBO
From $344 per night (USD)VRBO
BEAUTIFUL 4/20 FRIENDLY 2 BR 2 BA DUPLEX -TWO FLOORS - IN SIZZLING SOUTH SHORE!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We invite you to our beautiful home, minutes from Downtown, Hyde Park, Golfing, Fishing, and the Beach! Floor 1 feature ...
From $344 per night (USD)VRBO
From $617 per night (USD)Expedia
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 20
Imagine a stone castle, medieval style; except this one has an 85" HDTV, Wifi, 16' long granite bar with full kitchen an ...
From $617 per night (USD)Expedia
From $397 per night (USD)VRBO
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Summary: Newly renovated designer 2,500 square foot brick-and-timber loft with 15 foot ceilings located in the heart of ...
From $397 per night (USD)VRBO
From $376 per night (USD)VRBO
Luxury, spacious first floor brownstone in east Lincoln Park
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the best of Chicago’s neighborhoods, parks and lakefront from the comfort of this 2400 square foot home with two s ...
From $376 per night (USD)VRBO
From $669 per night (USD)VRBO
Wrigley Field MVP Suite 1 Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Recently built from the ground up and featured on the Travel Channel, you will love our beautifully furnished one-bedroo ...
From $669 per night (USD)VRBO
From $304 per night (USD)Expedia
NEW LUXURY CONDO WITH PATIO DECK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
OVERVIEW: This is a high end first floor condo that comfortably sleeps 5 persons. Luxury bathrooms. Fully equipped chef’ ...
From $304 per night (USD)Expedia
From $567 per night (USD)VRBO
Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our luxurious 2-bedroom, 2-bathroom townhouse located in the heart of south loop Chicago! This home is perfec ...
From $567 per night (USD)VRBO
From $105 per night (USD)Expedia
Cozy Loop 1BR, w/ W/D, Gym, nr Chicago Riverwalk 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 $105 per night (USD)Expedia
Click For PricingVRBO
Hip West Loop 2BR w/ Gym, Pool, near Fulton Market, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in West Loop with balcony views over the city. It’ll be ea ...
Click For PricingVRBO
From $140 per night (USD)Expedia
Mod West Loop 2BR w/ Gym, Pool, W/D, nr. Fulton Market, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in West Loop with balcony views over the city. It’ll be ea ...
From $140 per night (USD)Expedia
From $237 per night (USD)VRBO
Chic Gold Coast Convertible w/ Lounge near Oak Street by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Rush & Division with balcony views over the city. It’ll ...
From $237 per night (USD)VRBO
From $167 per night (USD)Expedia
Mod River North 2BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Rush & Division with high floor views over the city. It ...
From $167 per night (USD)Expedia
From $105 per night (USD)VRBO
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile, 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 $105 per night (USD)VRBO
From $104 per night (USD)Expedia
Roomy Loop 1BR w/ Gym, Pool, W/D, nr. Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Chicago Loop furnished one bedr ...
From $104 per night (USD)Expedia
From $199 per night (USD)VRBO
Smart Loop 1BR w/ Pool, Gym, nr. Financial District, 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 $199 per night (USD)VRBO
From $114 per night (USD)Expedia
Open River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Rush & Division with high floor views over the city. It ...
From $114 per night (USD)Expedia
From $99 per night (USD)VRBO
Roomy Loop 1BR w/ Pool, Gym, near Financial District, 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 $99 per night (USD)VRBO
From $137 per night (USD)Expedia
Cozy Loop 1BR w/ Pool, Gym, nr. 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 $137 per night (USD)Expedia
From $169 per night (USD)VRBO
Roomy River North 2BR w/ Gym, Deck & Pool, walk to Mag Mile, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Rush & Division furnished two bedroom ...
From $169 per night (USD)VRBO
From $110 per night (USD)Expedia
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile 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 $110 per night (USD)Expedia
From $120 per night (USD)VRBO
Lux River North 1BR w/ Gym, W/D, near Magnificent Mile, 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 $120 per night (USD)VRBO
From $104 per night (USD)Expedia
Lux River North 1BR w/ Gym, W/D, BBQ, Pool, 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 spacious Near North furnished one bedroom apa ...
From $104 per night (USD)Expedia
From $296 per night (USD)VRBO
Upgraded,Spacious 3 Bedroom Apartment.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Bright and beautiful top floor 1200 sq. ft, 3 bedrooms apartment located in Jefferson Park,9 minutes from O hare Interna ...
From $296 per night (USD)VRBO
Click For PricingExpedia
Smart West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, 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 ...
Click For PricingExpedia
From $211 per night (USD)VRBO
Ideal Gold Coast 2BR, w/ Gym, Lounge, W/D, nr Oak Street by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this charming two bedroom Blueground apartment. You’ll love coming ...
From $211 per night (USD)VRBO
From $180 per night (USD)Expedia
Lovely Gold Coast Convertible w/ Terrace near the L by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Rush & Division furnished one bedroom ...
From $180 per night (USD)Expedia
Click For PricingVRBO
Mod 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 roomy one bedroom Blueground apartment. You’ll love coming ho ...
Click For PricingVRBO
From $97 per night (USD)Expedia
Mod Gold Coast 1BR w/ Gym, nr. Magnificent Mile & the 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 $97 per night (USD)Expedia
From $167 per night (USD)VRBO
Smart South Loop 1BR w/ Pool & gym, near CTA Train, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this comfortable one bedroom Blueground apartment. You’ll love com ...
From $167 per night (USD)VRBO
From $836 per night (USD)Expedia
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to an amazing, 3-story art filled modern single family home in Chicago's vibrant RiverWest neighborhood. 3500 s ...
From $836 per night (USD)Expedia
From $457 per night (USD)VRBO
Gorgeous Home Near Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern design of a historic Chicago row house in one of the "cities best" neighborhoods. This home was totally redesigne ...
From $457 per night (USD)VRBO
From $317 per night (USD)VRBO
#1415 - 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 $317 per night (USD)VRBO
From $376 per night (USD)VRBO
#1605 - 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 $376 per night (USD)VRBO
From $415 per night (USD)VRBO
#1601 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $415 per night (USD)VRBO
From $400 per night (USD)VRBO
#1602 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $400 per night (USD)VRBO
From $382 per night (USD)VRBO
#1103 - 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 $184 per night (USD)VRBO
The Bright Retreat in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark St ...
From $184 per night (USD)VRBO
From $193 per night (USD)Expedia
The Avondale Guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This is a private three bedroom house you will be reserving in the Avondale neighborhood. Plenty of available free stree ...
From $193 per night (USD)Expedia
From $200 per night (USD)VRBO
Stunning Logan Square 2BR w/ Roof Deck & Gym, 1 block to L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Logan Square with balcony views over the city. It’ll be ...
From $200 per night (USD)VRBO
From $380 per night (USD)Expedia
NEW LUXURY PENTHOUSE CONDO
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
OVERVIEW: This is a spacious penthouse condo with an amazing city skyline view on private rooftop terrace. Comfortably s ...
From $380 per night (USD)Expedia
From $1109 per night (USD)VRBO
THE COMPOUND Large Exquisite House Private Yard ''Best Location'' Well Appointed
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 28
Walk to everything Chicago has to offer- Downtown and Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars ...
From $1109 per night (USD)VRBO
From $388 per night (USD)VRBO
Stunning Corner 2BR in the Loop | City & Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city an ...
From $388 per night (USD)VRBO
From $522 per night (USD)VRBO
Spectacular Corner 3BR in the Loop | City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stylish 1,400+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $522 per night (USD)VRBO
From $2796 per night (USD)Expedia
The Orleans - Entire Building - With Rooftop Deck!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: This property can be rented out and you would have access to the entire building which consists of 4 individual ...
From $2796 per night (USD)Expedia
From $214 per night (USD)VRBO
LOCATION!! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Luxury condo in a FANTASTIC location! Remodeled upscale condo located on the brink of River North/Gold Coast/Streetervil ...
From $214 per night (USD)VRBO
From $192 per night (USD)Expedia
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Av ...
From $192 per night (USD)Expedia
From $210 per night (USD)VRBO
Airy West Loop 1BR w/ Pool, Pet Spa, near Restaurant Row, 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 $210 per night (USD)VRBO
From $279 per night (USD)VRBO
Kasa | Modern Studio + Rooftop Sundeck | 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 $279 per night (USD)VRBO
From $299 per night (USD)VRBO
Kasa | Stylish Studio + Gym Access | 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 $299 per night (USD)VRBO
From $316 per night (USD)VRBO
Kasa | Relaxing Studio + Laptop Friendly | 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 $316 per night (USD)VRBO
From $346 per night (USD)VRBO
Kasa | Modern 1 BD + Pool Access |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 $346 per night (USD)VRBO
From $296 per night (USD)VRBO
Kasa | Modern Studio + Near the Magnificent Mile | 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 $296 per night (USD)VRBO
From $303 per night (USD)VRBO
Kasa | Bright & Airy Studio + Pool Access | 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 $303 per night (USD)VRBO
From $325 per night (USD)VRBO
Kasa | Fresh & Bright Studio + Pet Friendly | 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 $325 per night (USD)VRBO
From $384 per night (USD)VRBO
Kasa | Welcoming 1 BD + Gym Access | 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 $384 per night (USD)VRBO
From $299 per night (USD)VRBO
Kasa | Inviting Studio + Rooftop Sundeck | 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 $299 per night (USD)VRBO
From $356 per night (USD)VRBO
Kasa | Inviting Studio + Pet Friendly | 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 $356 per night (USD)VRBO
From $309 per night (USD)VRBO
Kasa | Welcoming Studio + Near Upscale Eateries | 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