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Chicago Rentals

From $278 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 $278 per night (USD)
VRBO
From $303 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 $303 per night (USD)
VRBO
$Sonder South Wabash | Superior One-Bedroom Apartment w\/ Balcony City View$
From $188 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 $188 per night (USD)
VRBO
From $285 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 $285 per night (USD)
VRBO
From $210 per night (USD)
VRBO
Kasa | Spectacular City Views | 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 $210 per night (USD)
VRBO
From $277 per night (USD)
VRBO
Kasa | Walk to Lincoln Park Zoo | 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 $277 per night (USD)
VRBO
From $201 per night (USD)
VRBO
Kasa | Spectacular City Views | 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 $201 per night (USD)
VRBO
From $280 per night (USD)
VRBO
Kasa | Walk to Lincoln Park Zoo | 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 $280 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Kasa | Spectacular City Views | 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 $205 per night (USD)
VRBO
From $283 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 $283 per night (USD)
VRBO
$MAG MILE MEGA ENTIRE FLOOR 4BD\/4BA+Parking&Rooftop$
From $617 per night (USD)
VRBO
MAG MILE MEGA ENTIRE FLOOR 4BD\/4BA+Parking&Rooftop
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 $617 per night (USD)
VRBO
$GROUP LUX in Old Town 4bd\/3ba (+Rooftop\/Parking)$
From $557 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 $557 per night (USD)
VRBO
From $238 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 $238 per night (USD)
VRBO
$Fantastic River North 1BR w\/ Gym, Rooftop, 1 block to L, by Blueground$
From $101 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 $101 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Sonder Greektown | Three-Bedroom Apartment
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Les vieilles traditions rencontrent les équipements modernes. Bienvenue à Greektown. Déposez vos bagages dans votre espa ...
From $237 per night (USD)
VRBO
From $180 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 $180 per night (USD)
VRBO
$Airy South Loop 1BR w\/ Lounge, Pool & Gym near Grant Park, by Blueground$
From $112 per night (USD)
VRBO
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 $112 per night (USD)
VRBO
$Bright South Loop 1BR w\/ Pool, Gym, walk to Museum Campus, by Blueground$
From $115 per night (USD)
Expedia
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 South Loop. with views over the city. It’ll be easy to ...
From $115 per night (USD)
Expedia
From $1072 per night (USD)
VRBO
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 $1072 per night (USD)
VRBO
$Roomy South Loop 1BR w\/ Pool, Lounge, walk to CTA Trains, by Blueground$
From $110 per night (USD)
Expedia
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 $110 per night (USD)
Expedia
From $2221 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 $2221 per night (USD)
VRBO
$Roomy Ravenswood 2BR w\/ Rooftop, BBQ, next to Brown line, by Blueground$
From $180 per night (USD)
Expedia
Roomy Ravenswood 2BR w\/ Rooftop, BBQ, next to Brown line, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Ravenswood furnished two bedroom apartme ...
From $180 per night (USD)
Expedia
$Modern South Loop 1BR w\/ Pool + Gym, walk to Soldier Field, by Blueground$
From $124 per night (USD)
VRBO
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 South Loop furnished one bedroom apar ...
From $124 per night (USD)
VRBO
$HUGE 1700 sqft 3bd West Loop Penthouse w\/ Balcony$
From $209 per night (USD)
Expedia
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 $209 per night (USD)
Expedia
From $286 per night (USD)
VRBO
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 $286 per night (USD)
VRBO
From $273 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 $273 per night (USD)
VRBO
From $432 per night (USD)
VRBO
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 $432 per night (USD)
VRBO
$Lovely River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $120 per night (USD)
Expedia
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 River North furnished one bedro ...
From $120 per night (USD)
Expedia
$Darling River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $114 per night (USD)
VRBO
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 River North. with views over the city. It’ll be easy to ...
From $114 per night (USD)
VRBO
$Ultra Modern Wicker Park Pad w\/ HUGE Outdoor Space$
From $243 per night (USD)
Expedia
Ultra Modern Wicker Park Pad w\/ HUGE Outdoor Space
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Our Townhouse sits in an incredible location. 1 minute away from 90/94 expressway, on a quiet cul-de-sac in Wicker Park. ...
From $243 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Walking distance to restaurants, shops and Lake Michigan,
Bedrooms:
2
Bathrooms:
4
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 $291 per night (USD)
VRBO
$Sleek River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $154 per night (USD)
Expedia
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 $154 per night (USD)
Expedia
$Smart River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $140 per night (USD)
VRBO
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 River North. with views over the city. It’ll be easy to ...
From $140 per night (USD)
VRBO
$Elegant Lakeview 1BR w\/ Gym, Pool, 1 block to Lincoln Park, by Blueground$
From $123 per night (USD)
Expedia
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 Lakeview furnished one bedroom ...
From $123 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Modern 4 Bedroom Greystone | White Sox
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Summary: Three story Greystone which still has the original charm with it's 2 story entrance is nestled within a very hi ...
From $211 per night (USD)
VRBO
From $281 per night (USD)
VRBO
Kasa | Walk to Lincoln Park Zoo | 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 $281 per night (USD)
VRBO
From $4624 per night (USD)
VRBO
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Bedrooms:
6
Bathrooms:
5
Sleeps:
14
Chicago’s Gold Coast Luxury Single Family Home. The location is so perfect it cannot be beat! IG: ChicagoLuxuryVRBO. Ho ...
From $4624 per night (USD)
VRBO
From $180 per night (USD)
VRBO
Great Location-Beautiful Friendly Andersonville Neighborhood
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
City of Chicago Vacation LICENSE NO.: 2209341 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful t ...
From $180 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Walking distance to restaurants, shops and Lake Michigan,
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Residence on the Avenue. A Spacious Vintage condo in a stunning 1928 Art Deco building on a tree lined avenue. We are a ...
From $247 per night (USD)
VRBO
From $116 per night (USD)
Expedia
Walking distance to Lake Michigan, shops and restaurants.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Sky View Condo at Residence on the Avenue is a spacious 1800 sq. ft condo . This is one of our 3 rentals. The Sky Vi ...
From $116 per night (USD)
Expedia
From $291 per night (USD)
VRBO
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We are happy to announce our 2nd Wrigleyville location. The Wrigleyville VIP sits just behind the Hotel Zachary, on the ...
From $291 per night (USD)
VRBO
From $285 per night (USD)
VRBO
One half block from Lincoln Park and the zoo
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Our place is a newly renovated.! You'll love the kitchen, the fireplace, the outdoor deck and it's coziness. Perfect for ...
From $285 per night (USD)
VRBO
$Family Friendly 2BD\/2BA Near Wrigley, Lincoln Square$
From $257 per night (USD)
VRBO
Family Friendly 2BD\/2BA Near Wrigley, Lincoln Square
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Live like a local in one of Chicago’s best neighborhoods at a top rated property! Located in a family-owned boutique bui ...
From $257 per night (USD)
VRBO
From $129 per night (USD)
VRBO
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
What guests like most? Super clean. Super comfortable. Super Host. Full use of second story fully furnished private apa ...
From $129 per night (USD)
VRBO
From $174 per night (USD)
VRBO
iKlektik House Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Fully furnished one bedroom in Ukrainian Village/West Town. Voted best top ten neighborhood in the United States. Close ...
From $174 per night (USD)
VRBO
$Charming River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $139 per night (USD)
Expedia
Charming 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 beautiful one bedroom Blueground apartment. You’ll love comin ...
From $139 per night (USD)
Expedia
$Rad River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $148 per night (USD)
VRBO
Rad 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 sophisticated one bedroom Blueground apartment. You’ll love c ...
From $148 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Angie & Mike's Nest!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Newly renovated three bedroom & 1 bath apartment with stainless steel appliances. The space The apartment is in the se ...
From $164 per night (USD)
Expedia
From $199 per night (USD)
VRBO
✨|Beautiful|Comfy|1br|✨LincolnSq.|Near Wrigley| ✨
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $199 per night (USD)
VRBO
From $249 per night (USD)
Expedia
✨Rustic Studio Apartment Heart of Lincoln Square✨
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $249 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Inviting Stylish Home with Covered Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The residence features a subtle boho-chic inspired aesthetic, rustic wood furnishings, a breakfast bar, an open-plan mai ...
From $274 per night (USD)
VRBO
From $262 per night (USD)
Expedia
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $262 per night (USD)
Expedia
From $229 per night (USD)
VRBO
🌟Spacious|Inviting 2BR Heart of Lively Lincoln Sq🌟
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $229 per night (USD)
VRBO
From $262 per night (USD)
Expedia
🌟Homey|Snuggly|Modern|1BR Lakeview - Near Wrigley🌟
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Lakeview is home to Wrigleyville, Wrigley field home of the Chicago Cubs and Belmont theatre district which has over 30 ...
From $262 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Soft Palate & Warm Bricks At A Rogers Park Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Meet NEW and CHARM with exposed brick,dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, open ...
From $355 per night (USD)
VRBO
From $625 per night (USD)
Expedia
Prime location Historic Chicago Townhouse
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago Located on one of the desirab ...
From $625 per night (USD)
Expedia
From $488 per night (USD)
VRBO
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Lincoln Park is one of the most coveted areas to live or stay in Chicago. DePaul University is less than a block away. L ...
From $488 per night (USD)
VRBO
From $241 per night (USD)
Expedia
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located right off main bustling streets in Logan Square, i.e. the famous Milwaukee Ave, you definitely won’t need a car ...
From $241 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is a beautifully remodeled, modern, spacious, and luxuriously furnished 3 bedroom, 2 bath private city apartment. ...
From $243 per night (USD)
VRBO
$Modern Lincoln Park Hideaway 1 Bd\/1Bath$
From $151 per night (USD)
Expedia
Modern Lincoln Park Hideaway 1 Bd\/1Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to a recently renovated sanctuary in the sought-after neighborhood of West Lincoln Park. Indulge in the abundance ...
From $151 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located in the heart of Chicago's premier entertainment district • Walk Score 93 (“Walker’s Paradise”) • Free street par ...
From $218 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Large Executive Historic Row house in Historic Pullman
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Welcome to Historic Pullman. This charming executive row house has everything you will need. The home is well appointe ...
From $205 per night (USD)
VRBO
$53\/54th Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Balcony$
From $477 per night (USD)
VRBO
53\/54th Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Balcony
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Embark on an extraordinary journey with Penthouse#3 – not just a rental, but a breathtaking haven in the heart of Chicag ...
From $477 per night (USD)
VRBO
$Exquisite Rogers Park 1bd\/1bath Apt. Near Evanston$
From $183 per night (USD)
Expedia
Exquisite Rogers Park 1bd\/1bath Apt. Near Evanston
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Recently remodeled 1 bedroom, 1 bath, plus sleeper sofa and kitchen with modern finishes on the top floor of a nice owne ...
From $183 per night (USD)
Expedia
$Tasteful Streeterville 1BR w\/ Gym, Pool, near Navy Pier, by Blueground$
From $111 per night (USD)
VRBO
Tasteful Streeterville 1BR w\/ Gym, Pool, near Navy Pier, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $111 per night (USD)
VRBO
$Bright Streeterville 2BR w\/ Gym, Pool, near Navy Pier, by Blueground$
From $204 per night (USD)
Expedia
Bright Streeterville 2BR w\/ Gym, Pool, near Navy Pier, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished two bedroom apar ...
From $204 per night (USD)
Expedia
$Deluxe South Loop 1BR w\/ Roof, Gym & Lounge, 1 block to L, by Blueground$
From $112 per night (USD)
VRBO
Deluxe South Loop 1BR w\/ Roof, Gym & Lounge, 1 block to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Discover the best of Chicago, with this one bedroom apartment in South Loop. . It’ll be easy to simply show up and start ...
From $112 per night (USD)
VRBO
From $518 per night (USD)
Expedia
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Bedrooms:
4
Bathrooms:
4
Sleeps:
24
Temporarily live in the best neighborhood in Chicago in an amazing Furnished Custom Single Family Home brought to you by ...
From $518 per night (USD)
Expedia
$51\/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center$
From $517 per night (USD)
VRBO
51\/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Indulge in the extraordinary at Penthouse#4 – not just a rental, but a magnificent haven soaring above Chicago. Picture ...
From $517 per night (USD)
VRBO
From $300 per night (USD)
Expedia
52th Floor Penthouse - Fireplace, VIEWS, grocery store in building.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with floor to ceiling window in ...
From $300 per night (USD)
Expedia
From $291 per night (USD)
VRBO
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with floor to ceiling window in ...
From $291 per night (USD)
VRBO
From $2130 per night (USD)
Expedia
2-beautiful adjacent luxury homes near downtown. Room for 20 adults.
Bedrooms:
5
Bathrooms:
8
Sleeps:
16
Two Modern large art filled spacious unique downtown townhouses in Chicago's happening RiverWest neighborhood. 6000+ sq ...
From $2130 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple dir ...
From $313 per night (USD)
VRBO
$3BR\/2.1BA TOWNHOUSE IN THE HEART OF WEST LOOP$
From $596 per night (USD)
Expedia
3BR\/2.1BA TOWNHOUSE IN THE HEART OF WEST LOOP
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Location, Location, Location! Welcome to our amazing 3 BD/2.1 BA townhome located in the most desirable West Loop neighb ...
From $596 per night (USD)
Expedia
From $147 per night (USD)
VRBO
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
Rest and Relax in a home away from home. Equipped with many perks, such as towels, air fryer, toiletries, and much more! ...
From $147 per night (USD)
VRBO
From $831 per night (USD)
Expedia
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Imagine yourself in PH#1, a spectacular and one-of-a-kind rental perched 55 stories above the pulse of Chicago. Picture ...
From $831 per night (USD)
Expedia
From $302 per night (USD)
VRBO
52nd Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Pool, WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This Downtown Chicago Penthouse unit is towering 52 stories above the city, with floor to ceiling windows in the living ...
From $302 per night (USD)
VRBO
From $360 per night (USD)
Expedia
53rd Floor MagMile Penthouse - VIEWS, Balcony, Pool, WiFi, & Fitness Center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Penthouse level unit is a magnificent unique rental in Chicago. Towering 50+ Floors above the city, this Penthouse ...
From $360 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Historic 1920s Private Bungalow Near Logan Square!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Before every reservation this home is Professionally CLEANED and SANITIZED thoroughly from top to bottom. Our single f ...
From $405 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Luxurious 3Br with parking on premises 🌔
Bedrooms:
1
Bathrooms:
4
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 $218 per night (USD)
Expedia
$Modern Lakeview 1BR w\/ Gym, Pool, 1 block to Lincoln Park, by Blueground$
From $143 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 Lakeview. with high floor views over the city. It’ll be ...
From $143 per night (USD)
VRBO
From $450 per night (USD)
VRBO
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With ...
From $450 per night (USD)
VRBO
Click For Pricing
VRBO
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 Pricing
VRBO
$Belmont House, Classy & Chic\/walk to Wrigley Field$
From $214 per night (USD)
Expedia
Belmont House, Classy & Chic\/walk to Wrigley Field
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This gorgeous home is smack-dab in one of the hottest neighborhoods in Chicago, a 3/4 mile 15 minute walk to Wrigley Fie ...
From $214 per night (USD)
Expedia
From $309 per night (USD)
VRBO
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Bedrooms:
4
Bathrooms:
4
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 $309 per night (USD)
VRBO
$Bright\/Cozy\/Hip 2\/1 Apt | Logan Square$
From $154 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 $154 per night (USD)
VRBO
From $255 per night (USD)
VRBO
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 $255 per night (USD)
VRBO
$Mod River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $170 per night (USD)
Expedia
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 River North. with views over the city. It’ll be easy to ...
From $170 per night (USD)
Expedia
$Trendy River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $167 per night (USD)
VRBO
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 $167 per night (USD)
VRBO
From $329 per night (USD)
VRBO
Private Historic Coach House Wicker Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Location, location, location! Private quiet clean coach house with two bedrooms and one bath in the heart of Wicker Park ...
From $329 per night (USD)
VRBO
Click For Pricing
VRBO
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Great 3Br 2Ba condo with a king bed in the primary bedroom. You'll feel at home with all the amenities just 5 miles from ...
Click For Pricing
VRBO
From $358 per night (USD)
Expedia
The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Designer urban feel - completely rehabbed - reclaimed wood beams - full walk in glass master shower with an exposed bric ...
From $358 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple dir ...
From $306 per night (USD)
VRBO
$Airy River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $105 per night (USD)
Expedia
Airy 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 comfortable River North furnished one bedroom ...
From $105 per night (USD)
Expedia
$Downtown Park VIEWS Mich Ave, Museums 2bd\/2ba$
From $301 per night (USD)
VRBO
Downtown Park VIEWS Mich Ave, Museums 2bd\/2ba
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Welcome to our Michigan Ave, Grant ...
From $301 per night (USD)
VRBO
$DOWNTOWN PENTHOUSE #1 Vintage 2BD\/1BA Grank Park, Museums$
From $268 per night (USD)
Expedia
DOWNTOWN PENTHOUSE #1 Vintage 2BD\/1BA Grank Park, Museums
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Welcome to our 2-bd in the HEART of ...
From $268 per night (USD)
Expedia
From $639 per night (USD)
VRBO
FIVE STAR Single Family in Heart Of Chicago! Super clean, Great Neighborhood
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Welcome to Chicago! We're thrilled you're considering our home for your trip. Our Chicago brick home, adjacent to a beau ...
From $639 per night (USD)
VRBO
$Beautiful Streeterville 1BR w\/ Gym, Pool, near Navy Pier, by Blueground$
From $97 per night (USD)
Expedia
Beautiful Streeterville 1BR w\/ Gym, Pool, near Navy Pier, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Streeterville. with high floor views over the city. It’ ...
From $97 per night (USD)
Expedia
$DOWNTOWN PENTHOUSE #2 Vintage 3BD\/1BA Family-Friendly, Grant Park & Museums$
From $382 per night (USD)
VRBO
DOWNTOWN PENTHOUSE #2 Vintage 3BD\/1BA Family-Friendly, Grant Park & Museums
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Welcome to our 3-bd Penthouse! We ...
From $382 per night (USD)
VRBO
$Splendid Streeterville 1BR w\/ Gym, Pool, near Navy Pier, by Blueground$
From $82 per night (USD)
Expedia
Splendid Streeterville 1BR w\/ Gym, Pool, near Navy Pier, 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 $82 per night (USD)
Expedia

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