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Chicago Rentals

From $246 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 $246 per night (USD)
VRBO
$Cozy Loop 1BR w\/ Pool, Gym, nr. Merchandise Mart & L, by Blueground$
From $198 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’l ...
From $198 per night (USD)
Expedia
$Spacious Loop 2BR w\/ Gym, Doorman, walk to L & Parks, by Blueground$
From $161 per night (USD)
VRBO
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 $161 per night (USD)
VRBO
$Generous Loop 2BR w\/ Gym, Doorman, walk to L & Parks, by Blueground$
Click For Pricing
Expedia
Generous Loop 2BR w\/ Gym, Doorman, walk to L & Parks, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in The Loop. with views over the city. It’ll be easy to si ...
Click For Pricing
Expedia
From $429 per night (USD)
VRBO
Modern Wrigley Oasis with Parking!
Bedrooms:
4
Bathrooms:
2
Sleeps:
6
Beautifully designed in the heart of Wrigley. Steps away from Wrigley Field, bars, restaurants and shops! This modern oa ...
From $429 per night (USD)
VRBO
From $1140 per night (USD)
Expedia
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 $1140 per night (USD)
Expedia
From $1777 per night (USD)
VRBO
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME!!! ABSOLUTELY NO PARTIES OR LARGE GATHERINGS! We reserve the right t ask ...
From $1777 per night (USD)
VRBO
$Premium Lakeview 2BR w\/ Patio, W\/D, walk to Wrigley Field, by Blueground$
From $167 per night (USD)
Expedia
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 $167 per night (USD)
Expedia
$Modern Streeterville 1BR w\/ Gym, Pool, walk to Navy Pier, by Blueground$
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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 ...
Click For Pricing
VRBO
$Hip River North 1BR w\/ Gym, W\/D, near Magnificent Mile, by Blueground$
Click For Pricing
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 lovely Rush & Division furnished one bedroom ...
Click For Pricing
Expedia
$Sleek West Loop 1BR w\/ Gym, Pool, near Fulton Market, by Blueground$
From $166 per night (USD)
VRBO
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 $166 per night (USD)
VRBO
$Airy Loop 2BR w\/ Pool, Gym, nr. Financial District & the L, by Blueground$
From $111 per night (USD)
Expedia
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 b ...
From $111 per night (USD)
Expedia
From $164 per night (USD)
VRBO
Gorgeous Gold Coast 1BR nr. Mariano Park & Oak St. Beach, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this spacious Gold Coast furnished one bedroom apa ...
From $164 per night (USD)
VRBO
$Hip River North 1BR w\/ Pool + Roof Deck near Mag Mile, by Blueground$
From $177 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 $177 per night (USD)
Expedia
$Premium Logan Square 1BR w\/ Roof Deck & Gym, 1 block to L, by Blueground$
From $178 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 $178 per night (USD)
VRBO
From $1269 per night (USD)
Expedia
Stylish 6 Bedroom Home in Trendy Logan Square!
Bedrooms:
4
Bathrooms:
8
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 $1269 per night (USD)
Expedia
From $4626 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 $4626 per night (USD)
VRBO
From $393 per night (USD)
Expedia
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 $393 per night (USD)
Expedia
From $320 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 $320 per night (USD)
VRBO
From $305 per night (USD)
Expedia
NEW LUXURY CONDO WITH PATIO DECK
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
OVERVIEW: This is a high end first floor condo that comfortably sleeps 5 persons. Luxury bathrooms. Fully equipped chef’ ...
From $305 per night (USD)
Expedia
From $591 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 $591 per night (USD)
VRBO
$Cozy Loop 1BR, w\/ W\/D, Gym, nr Chicago Riverwalk by Blueground$
From $253 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 $253 per night (USD)
Expedia
$Hip West Loop 2BR w\/ Gym, Pool, near Fulton Market, by Blueground$
From $328 per night (USD)
VRBO
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 e ...
From $328 per night (USD)
VRBO
$Mod West Loop 2BR w\/ Gym, Pool, W\/D, nr. Fulton Market, by Blueground$
From $212 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 e ...
From $212 per night (USD)
Expedia
$Chic Gold Coast Convertible w\/ Lounge near Oak Street by Blueground$
From $170 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’l ...
From $170 per night (USD)
VRBO
$Mod River North 2BR w\/ Gym, W\/D, near Magnificent Mile, by Blueground$
From $141 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. I ...
From $141 per night (USD)
Expedia
$Sleek Loop 2BR w\/ Gym, Pool, W\/D, nr. Financial District, by Blueground$
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VRBO
Sleek Loop 2BR w\/ Gym, Pool, W\/D, nr. Financial District, 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 b ...
Click For Pricing
VRBO
$Hip River North 1BR w\/ Pool + Roof Deck near Mag Mile, by Blueground$
From $239 per night (USD)
Expedia
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 ...
From $239 per night (USD)
Expedia
$Roomy Loop 1BR w\/ Gym, Pool, W\/D, nr. Millennium Park, by Blueground$
From $111 per night (USD)
VRBO
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 $111 per night (USD)
VRBO
$Smart Loop 1BR w\/ Pool, Gym, nr. Financial District, by Blueground$
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
$Open River North 1BR w\/ Gym, W\/D, near Magnificent Mile, by Blueground$
From $176 per night (USD)
VRBO
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. I ...
From $176 per night (USD)
VRBO
$Roomy Loop 1BR w\/ Pool, Gym, near Financial District, by Blueground$
From $230 per night (USD)
Expedia
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 $230 per night (USD)
Expedia
$Cozy Loop 1BR w\/ Pool, Gym, nr. L, by Blueground$
From $152 per night (USD)
VRBO
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’l ...
From $152 per night (USD)
VRBO
$Roomy River North 2BR w\/ Gym, Deck & Pool, walk to Mag Mile, by Blueground$
From $141 per night (USD)
Expedia
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 $141 per night (USD)
Expedia
$Hip River North 1BR w\/ Pool + Roof Deck near Mag Mile by Blueground$
From $115 per night (USD)
VRBO
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 $115 per night (USD)
VRBO
$Lux River North 1BR w\/ Gym, W\/D, near Magnificent Mile, by Blueground$
From $140 per night (USD)
Expedia
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 $140 per night (USD)
Expedia
$Lux River North 1BR w\/ Gym, W\/D, BBQ, Pool, near Mag Mile, by Blueground$
From $113 per night (USD)
VRBO
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 $113 per night (USD)
VRBO
$Smart West Loop 1BR w\/ Pool, Gym, nr. Restaurant Row, by Blueground$
From $156 per night (USD)
Expedia
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 ...
From $156 per night (USD)
Expedia
$Ideal Gold Coast 2BR, w\/ Gym, Lounge, W\/D, nr Oak Street by Blueground$
From $191 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 $191 per night (USD)
VRBO
$Lovely Gold Coast Convertible w\/ Terrace near the L by Blueground$
From $170 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 $170 per night (USD)
Expedia
$Mod Loop 1BR w\/ Gym, Pool, W\/D, nr. Financial District, by Blueground$
Click For Pricing
VRBO
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 Pricing
VRBO
$Mod Gold Coast 1BR w\/ Gym, nr. Magnificent Mile & the L, by Blueground$
From $170 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’l ...
From $170 per night (USD)
Expedia
$Smart South Loop 1BR w\/ Pool & gym, near CTA Train, by Blueground$
From $206 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 $206 per night (USD)
VRBO
$Stunning MODERN Home Downtown\/RiverWest Close to Fulton Market & United Center$
From $975 per night (USD)
Expedia
Stunning MODERN Home Downtown\/RiverWest Close to Fulton Market & United Center
Bedrooms:
4
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 $975 per night (USD)
Expedia
From $569 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 $569 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Beautiful 2BR 2 BATH 10 Minutes from the United Center!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Immerse yourself in the city life by staying in this hidden gem that features a full kitchen perfect for cooking, 15 ft ...
From $314 per night (USD)
Expedia
$Airy Lakeview 1BR w\/ W\/D, 1 block to L, near Wrigley Field, by Blueground$
From $155 per night (USD)
VRBO
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 $155 per night (USD)
VRBO
From $425 per night (USD)
Expedia
#1415 - Kasa Magnificent Mile Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
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)
Expedia
From $425 per night (USD)
VRBO
#1605 - Kasa Magnificent Mile Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
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 $919 per night (USD)
Expedia
#1601 - Kasa Magnificent Mile Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $919 per night (USD)
Expedia
From $1169 per night (USD)
VRBO
#1602 - Kasa Magnificent Mile Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $1169 per night (USD)
VRBO
From $408 per night (USD)
Expedia
#1103 - Kasa Magnificent Mile Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
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)
Expedia
From $391 per night (USD)
VRBO
#1812 - Kasa Magnificent Mile Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $391 per night (USD)
VRBO
From $589 per night (USD)
Expedia
#1402 - Kasa Magnificent Mile Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $589 per night (USD)
Expedia
From $411 per night (USD)
VRBO
#1916 - Kasa Magnificent Mile Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $411 per night (USD)
VRBO
$1 #33 - 4 Bedroom \/ 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown$
From $490 per night (USD)
Expedia
1 #33 - 4 Bedroom \/ 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Bedrooms:
2
Bathrooms:
5
Sleeps:
20
Beautiful and newly furnished condo in the heart of Chicago Chinatown area with 4 bedrooms, 2 baths, a spacious living r ...
From $490 per night (USD)
Expedia
$3 Bedroom\/ 2 Bathroom Luxury Suite in Vibrant Andersonville$
From $680 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 $680 per night (USD)
VRBO
From $440 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 $440 per night (USD)
Expedia
$Trendy West Town Flat - 2 bed \/ 1.5 bath with parking$
From $298 per night (USD)
VRBO
Trendy West Town Flat - 2 bed \/ 1.5 bath with parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Find your wanderlust in this perfectly located West Town condo. Situated between Chicago’s West Loop and Wicker Park ne ...
From $298 per night (USD)
VRBO
From $721 per night (USD)
Expedia
The Greenleaf House—Whole House
Bedrooms:
3
Bathrooms:
9
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 $721 per night (USD)
Expedia
From $688 per night (USD)
VRBO
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This corner apartment is in a perfect location with panoramic city views in multiple directions. With over 1,20 ...
From $688 per night (USD)
VRBO
From $406 per night (USD)
Expedia
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 $406 per night (USD)
Expedia
Click For Pricing
VRBO
Lakeview Greystone One Block From Wrigleyfield
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Experience Chicago like a local with your own professionally cleaned apartment. Step into the rainfall shower for a refr ...
Click For Pricing
VRBO
From $1072 per night (USD)
Expedia
Gorgeous 4 Bedroom with Pool Table steps from Wrigley Field Sleeps 9
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up and ...
From $1072 per night (USD)
Expedia
From $892 per night (USD)
VRBO
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
Bedrooms:
2
Bathrooms:
4
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 $892 per night (USD)
VRBO
From $1756 per night (USD)
Expedia
Stunning Designer Loft in Fulton Market, Sleeps 24 | Featured In Architectural D
Bedrooms:
4
Bathrooms:
7
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 $1756 per night (USD)
Expedia
From $788 per night (USD)
VRBO
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Summary: Newly renovated designer 2,500 square foot brick-and-timber loft with 15 foot ceilings located in the heart of ...
From $788 per night (USD)
VRBO
Click For Pricing
Expedia
Bucktown Bungalow *Prime Location* Private Roof Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spend your summer vacation lounging on the roof deck at our lovely Bucktown home! Perfect location to explore all that C ...
Click For Pricing
Expedia
From $344 per night (USD)
VRBO
Luxury, spacious first floor brownstone in east Lincoln Park
Bedrooms:
3
Bathrooms:
4
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 $344 per night (USD)
VRBO
From $529 per night (USD)
Expedia
Wrigleyville Inn, Beautiful Modern 1 Bedroom, Steps from Wrigley Field
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 $529 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Sonder Jewelers Row | Two-Bedroom Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Jewelers Row is the architectural gem of the Chicago Loop. Designed by Adler and Sullivan, the innovative style adds a m ...
From $499 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Sonder Jewelers Row | Superior One-Bedroom Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Jewelers Row is the architectural gem of the Chicago Loop. Designed by Adler and Sullivan, the innovative style adds a m ...
From $289 per night (USD)
VRBO
From $581 per night (USD)
VRBO
Sonder Jewelers Row | Superior Two-Bedroom Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Jewelers Row is the architectural gem of the Chicago Loop. Designed by Adler and Sullivan, the innovative style adds a m ...
From $581 per night (USD)
VRBO
From $499 per night (USD)
VRBO
Sonder The Plymouth | Spacious Three-Bedroom Apartment
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $499 per night (USD)
VRBO
From $762 per night (USD)
VRBO
Sonder The Plymouth | Four-Bedroom Apartment
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $762 per night (USD)
VRBO
From $477 per night (USD)
VRBO
Sonder The Plymouth | Two-Bedroom Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $477 per night (USD)
VRBO
From $618 per night (USD)
VRBO
Sonder The Plymouth | Superior Three-Bedroom Apartment
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $618 per night (USD)
VRBO
$Sonder South Wabash | Superior One-Bedroom Apartment w\/ Balcony City View$
From $446 per night (USD)
VRBO
Sonder South Wabash | Superior One-Bedroom Apartment w\/ Balcony City View
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to South Wabash — your modern South Loop sanctuary. Where each sophisticated space includes a fully equipped kit ...
From $446 per night (USD)
VRBO
From $592 per night (USD)
VRBO
Sonder The Plymouth | Three-Bedroom Apartment
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $592 per night (USD)
VRBO
From $402 per night (USD)
Expedia
#1516 - Kasa Magnificent Mile Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $402 per night (USD)
Expedia
From $645 per night (USD)
VRBO
#1902 - Kasa Magnificent Mile Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $645 per night (USD)
VRBO
From $470 per night (USD)
Expedia
#2003 - Kasa Magnificent Mile Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $470 per night (USD)
Expedia
From $657 per night (USD)
VRBO
#1401 - Kasa Magnificent Mile Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $657 per night (USD)
VRBO
From $427 per night (USD)
Expedia
#1515 - Kasa Magnificent Mile Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $427 per night (USD)
Expedia
From $637 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 $637 per night (USD)
VRBO
From $1172 per night (USD)
Expedia
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 $1172 per night (USD)
Expedia
$GROUP LUX in Old Town 4bd\/3ba (+Rooftop\/Parking)$
From $1006 per night (USD)
VRBO
GROUP LUX in Old Town 4bd\/3ba (+Rooftop\/Parking)
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertai ...
From $1006 per night (USD)
VRBO
From $240 per night (USD)
Expedia
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 $240 per night (USD)
Expedia
$Fantastic River North 1BR w\/ Gym, Rooftop, 1 block to L, by Blueground$
From $159 per night (USD)
VRBO
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 $159 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Sonder Greektown | Three-Bedroom Apartment
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Tradition meets modern amenities at Greektown. In the heart of this historic neighborhood, your stylish space includes a ...
From $223 per night (USD)
VRBO
From $332 per night (USD)
VRBO
Sonder Greektown | One-Bedroom Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tradition meets modern amenities at Greektown. In the heart of this historic neighborhood, your stylish space includes a ...
From $332 per night (USD)
VRBO
$Airy South Loop 1BR w\/ Lounge, Pool & Gym near Grant Park, by Blueground$
From $190 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 ...
From $190 per night (USD)
Expedia
$Bright South Loop 1BR w\/ Pool, Gym, walk to Museum Campus, by Blueground$
From $218 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 eas ...
From $218 per night (USD)
VRBO
From $1291 per night (USD)
Expedia
Featured on the Travel Channel, 4 Bedroom 2 Bath in Wrigley Rooftop Building
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 $1291 per night (USD)
Expedia
$Roomy South Loop 1BR w\/ Pool, Lounge, walk to CTA Trains, by Blueground$
From $214 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 $214 per night (USD)
VRBO
From $2045 per night (USD)
Expedia
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 $2045 per night (USD)
Expedia
$Roomy Ravenswood 2BR w\/ Rooftop, BBQ, next to Brown line, by Blueground$
From $185 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 $185 per night (USD)
VRBO
$Modern South Loop 1BR w\/ Pool + Gym, walk to Soldier Field, by Blueground$
From $208 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 $208 per night (USD)
Expedia
$HUGE 1700 sqft 3bd West Loop Penthouse w\/ Balcony$
From $384 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 $384 per night (USD)
VRBO
From $443 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, open ...
From $443 per night (USD)
Expedia

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