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Chicago Rentals

$Smart Loop 1BR w\/ Gym, Pool, near Financial District, by Blueground$
From $202 per night (USD)
VRBO
Smart Loop 1BR w\/ Gym, Pool, near Financial District, 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 $202 per night (USD)
VRBO
$Gorgeous NEW 5 BDR\/ 4BA in Logan Square w\/Parking!$
From $1089 per night (USD)
Expedia
Gorgeous NEW 5 BDR\/ 4BA in Logan Square w\/Parking!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
In desirable LOGAN SQUARE - 10 minutes from Downtown Chicago, steps away from the new Restaurant Row on Diversey Avenue! ...
From $1089 per night (USD)
Expedia
From $492 per night (USD)
VRBO
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Beautiful, modern and newly furnished 4br/2 bath condo at a desirable location for business conventions and vacation tra ...
From $492 per night (USD)
VRBO
$1 #12 - 2 Bedroom \/ 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown$
From $257 per night (USD)
Expedia
1 #12 - 2 Bedroom \/ 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Beautiful, newly renovated condo located in the heart of Chicago Chinatown with 2 bedroom, 1 bath, a spacious living roo ...
From $257 per night (USD)
Expedia
$4 #2N - 4 Bedroom \/ 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown$
From $508 per night (USD)
VRBO
4 #2N - 4 Bedroom \/ 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Newly remodeled apartment with 4 bedrooms, 4 bathrooms, a spacious & modern living area, FREE private parking and plenty ...
From $508 per night (USD)
VRBO
$4 #1S - 4 Bedroom \/ 1.5 Bath Condo near McCormick Place, Wintrust Arena$
From $470 per night (USD)
Expedia
4 #1S - 4 Bedroom \/ 1.5 Bath Condo near McCormick Place, Wintrust Arena
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Beautiful, modern and newly furnished 4 br/1.5 bath condo at a desirable location for both business conventions and vaca ...
From $470 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Welcome to Your Charming Oasis! Step into this delightful 3-BR, 1-BA retreat in a friendly neighborhood with views of a ...
From $303 per night (USD)
VRBO
$McCormick Place 2b\/2b family unit with optional parking for up to 8 guests$
Click For Pricing
Expedia
McCormick Place 2b\/2b family unit with optional parking for up to 8 guests
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • City Skyline view • ...
Click For Pricing
Expedia
From $1788 per night (USD)
VRBO
Spectacular Fulton Market Penthouse, Sleeps 24 in Style | Featured In Architectu
Bedrooms:
4
Bathrooms:
8
Sleeps:
24
Summary: 2 side-by-side designer penthouse apartments comprising 5,000 square feet (the entire top floor) of a brick-and ...
From $1788 per night (USD)
VRBO
From $1107 per night (USD)
VRBO
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: Stunning 2,500 square foot brick-and-timber luxury penthouse with 15 foot ceilings located in the heart of the ...
From $1107 per night (USD)
VRBO
$2\/2 Apt in the City | Downtown Chicago$
From $365 per night (USD)
VRBO
2\/2 Apt in the City | Downtown Chicago
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: LOCATION! LOCATION! LOCATION! DOWNTOWN CHICAGO! The perfect crash pad (*NO PARTIES*) to explore the heart o ...
From $365 per night (USD)
VRBO
From $661 per night (USD)
Expedia
Million Dollar Views! Luxury Downtown Skyhouse!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Stunning, Floor to Ceiling Panoramic Skyline Views from this Spacious 3-Bedroom, 2.5 Bath Apartment in the Sky! Located ...
From $661 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Suite 1 on Southport 4 Queen Beds!
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Check out our brand new construction Suite on Southport Ave. Centrally located in the world famous Lincoln Park ...
From $493 per night (USD)
VRBO
From $226 per night (USD)
Expedia
Chic, Cozy home, by Blue Line Train Stop + Free parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax in this chic and artfully designed condo. This sun-kissed 1-bedroom apartment in Irving Park is located in the cit ...
From $226 per night (USD)
Expedia
From $393 per night (USD)
VRBO
#1913 - 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 $393 per night (USD)
VRBO
From $388 per night (USD)
VRBO
#1803 - 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 $388 per night (USD)
VRBO
From $1042 per night (USD)
VRBO
#1901 - 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 $1042 per night (USD)
VRBO
From $860 per night (USD)
VRBO
Designer 3BR Luxury Penthouse in Heart of Fulton Market | Featured In Architectu
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: Spectacular 2,500 square foot brick-and-timber penthouse with 15 foot ceilings located in the heart of the vibr ...
From $860 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your getaway location in the heart of the Roscoe Village neighborhood of Chicago! A short walk to Wrigley Fie ...
From $371 per night (USD)
VRBO
From $769 per night (USD)
VRBO
#2002 - 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 $769 per night (USD)
VRBO
$LUXURIOUS LINCOLN PARK Home w\/ Rooftop (+parking)$
From $658 per night (USD)
VRBO
LUXURIOUS LINCOLN PARK Home w\/ Rooftop (+parking)
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Escape into this Lincoln Park Masterpiece! Guests love this home because: - Surrounded by top-notch restaurants/retai ...
From $658 per night (USD)
VRBO
From $548 per night (USD)
VRBO
Smart Home in Logan Square by the 606 Trail
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This property is a smart home with 3 bedrooms and 2 1/2 bathrooms, with a garage for a small to medium size SUV, which c ...
From $548 per night (USD)
VRBO
From $328 per night (USD)
VRBO
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Introducing your perfect short-term rental for a Chicago getaway! Nestled in the heart of historic Bronzeville, just a 1 ...
From $328 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Luxury Home Away From Your Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is a newly rehab house remodeled a year ago this house is your home away from home!! Upstairs Downstairs All Bedroo ...
From $234 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Charming 1 Bedroom entire Apartment - 1 Mile from Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Wonderful and spacious 1 bedroom apartment in the Northside of Chicago. Strong WiFi for your business and viewing. Right ...
From $169 per night (USD)
VRBO
From $606 per night (USD)
VRBO
Chic 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 $606 per night (USD)
VRBO
From $272 per night (USD)
VRBO
Trendy|Comfortable|1BR|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 $272 per night (USD)
VRBO
From $397 per night (USD)
VRBO
#2005 - 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 $397 per night (USD)
VRBO
From $1154 per night (USD)
VRBO
#1502 - 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 $1154 per night (USD)
VRBO
From $615 per night (USD)
VRBO
#1102 - 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 $615 per night (USD)
VRBO
From $409 per night (USD)
VRBO
#1105 - 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 $409 per night (USD)
VRBO
$❤️‍🔥MAGNIFICENT NEW Home w\/8 Beds & Free Parking❤️‍🔥$
From $943 per night (USD)
VRBO
❤️‍🔥MAGNIFICENT NEW Home w\/8 Beds & Free Parking❤️‍🔥
Bedrooms:
4
Bathrooms:
4
Sleeps:
17
Summary: Our home is a brand-new construction single family residence. Construction was complete in the summer of 2021. ...
From $943 per night (USD)
VRBO
From $284 per night (USD)
VRBO
Charming|Comfortable|1BR|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 $284 per night (USD)
VRBO
From $348 per night (USD)
VRBO
❤️ Stylish and Cozy 2BR in Logan Square!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Chicago! Our large 2-bedroom/1 bathroom apartment unit is perfect for getaway to Chicago. Stretch out on ...
From $348 per night (USD)
VRBO
From $263 per night (USD)
VRBO
3BR Spacious Home Away From Home. Coziest neighborhood in Chicago.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to the Windy City and home of amazing restaurants, great sports teams, and of course the lake! Whether you are t ...
From $263 per night (USD)
VRBO
$4\/2 Home + Foosball Table | Near Wrigley$
From $463 per night (USD)
VRBO
4\/2 Home + Foosball Table | Near Wrigley
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Welcome to this four bedroom, two bathroom apartment located in the neighborhood of Lakeview. The location is f ...
From $463 per night (USD)
VRBO
$Roomy Lincoln Park 2BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground$
From $180 per night (USD)
VRBO
Roomy Lincoln Park 2BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Lincoln Park. . It’ll be easy to simply show up and sta ...
From $180 per night (USD)
VRBO
$Sleek Lincoln Park 1BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground$
From $149 per night (USD)
Expedia
Sleek Lincoln Park 1BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Lincoln Park furnished one bedroom ...
From $149 per night (USD)
Expedia
$Ideal Lincoln Park 1BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground$
From $128 per night (USD)
VRBO
Ideal Lincoln Park 1BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this cheery Lincoln Park furnished one bedroom apa ...
From $128 per night (USD)
VRBO
From $175 per night (USD)
Expedia
A Peaceful 2BR Lincoln Park Coach House - FREE PARKING
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Elegantly decorated and cozy 2-bedroom apartment. Both bedrooms have queen beds. Some Highlights: ✔Free parking in the ...
From $175 per night (USD)
Expedia
$\Holy Cow\! 4bed 4bath Duplex Penthouse w\/ 3,000 sqft Private Roof-Deck!$
From $1523 per night (USD)
VRBO
\"Holy Cow\"! 4bed 4bath Duplex Penthouse w\/ 3,000 sqft Private Roof-Deck!
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
"Wow" Step outside & be face-to-face with the iconic Wrigley Field, home of the Chicago Cubs!! Best Space in Wrigley! ...
From $1523 per night (USD)
VRBO
$Roomy South Loop 1BR w\/ Pool, Lounge, walk to CTA Trains, by Blueground$
From $188 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 $188 per night (USD)
Expedia
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 $178 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 $178 per night (USD)
Expedia
$Bright South Loop 1BR w\/ Pool, Gym, walk to Museum Campus, by Blueground$
From $190 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 $190 per night (USD)
VRBO
From $241 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 $241 per night (USD)
Expedia
$Fantastic River North 1BR w\/ Gym, Rooftop, 1 block to L, by Blueground$
From $185 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 $185 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
$Roomy Ravenswood 2BR w\/ Rooftop, BBQ, next to Brown line, by Blueground$
From $195 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 $195 per night (USD)
VRBO
$Modern South Loop 1BR w\/ Pool + Gym, walk to Soldier Field, by Blueground$
From $196 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 $196 per night (USD)
Expedia
$HUGE 1700 sqft 3bd West Loop Penthouse w\/ Balcony$
From $395 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 $395 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
From $791 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 $791 per night (USD)
VRBO
From $469 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 $469 per night (USD)
Expedia
$Lovely River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $100 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 $100 per night (USD)
VRBO
$Darling River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground$
From $197 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 ...
From $197 per night (USD)
Expedia
$Ultra Modern Wicker Park Pad w\/ HUGE Outdoor Space$
Click For Pricing
VRBO
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. ...
Click For Pricing
VRBO
From $338 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 $338 per night (USD)
VRBO
From $659 per night (USD)
VRBO
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 $659 per night (USD)
VRBO
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 $395 per night (USD)
VRBO
#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 $395 per night (USD)
VRBO
From $561 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 $561 per night (USD)
VRBO
From $346 per night (USD)
VRBO
#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 $346 per night (USD)
VRBO
From $651 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 $651 per night (USD)
VRBO
From $430 per night (USD)
VRBO
#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 $430 per night (USD)
VRBO
From $640 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 $640 per night (USD)
VRBO
From $1137 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 $1137 per night (USD)
VRBO
$GROUP LUX in Old Town 4bd\/3ba (+Rooftop\/Parking)$
From $1020 per night (USD)
Expedia
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 $1020 per night (USD)
Expedia
From $885 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 $885 per night (USD)
VRBO
From $1711 per night (USD)
VRBO
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 $1711 per night (USD)
VRBO
From $381 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 $381 per night (USD)
VRBO
$DOWNTOWN PENTHOUSE Vintage Loft #6 2bd\/1.5ba +private balcony & gym$
From $529 per night (USD)
Expedia
DOWNTOWN PENTHOUSE Vintage Loft #6 2bd\/1.5ba +private balcony & gym
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Welcome to our 2-bd Penthouse Loft ...
From $529 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 $794 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 $794 per night (USD)
VRBO
Click For Pricing
VRBO
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
VRBO
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
$Smart West Loop 1BR w\/ Pool, Gym, nr. Restaurant Row, by Blueground$
From $165 per night (USD)
VRBO
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 $165 per night (USD)
VRBO
$Ideal Gold Coast 2BR, w\/ Gym, Lounge, W\/D, nr Oak Street by Blueground$
From $191 per night (USD)
Expedia
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)
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 $614 per night (USD)
VRBO
#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 $614 per night (USD)
VRBO
$1 #33 - 4 Bedroom \/ 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown$
From $490 per night (USD)
VRBO
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)
VRBO
$3 Bedroom\/ 2 Bathroom Luxury Suite in Vibrant Andersonville$
From $685 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 $685 per night (USD)
VRBO
From $440 per night (USD)
VRBO
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)
VRBO
$Trendy West Town Flat - 2 bed \/ 1.5 bath with parking$
From $288 per night (USD)
Expedia
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 $288 per night (USD)
Expedia
From $678 per night (USD)
VRBO
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 $678 per night (USD)
VRBO
From $697 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 $697 per night (USD)
VRBO
From $406 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 $406 per night (USD)
VRBO
From $302 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 $302 per night (USD)
Expedia
From $599 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 $599 per night (USD)
VRBO
$Cozy Loop 1BR, w\/ W\/D, Gym, nr Chicago Riverwalk by Blueground$
From $249 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 $249 per night (USD)
Expedia
$Hip West Loop 2BR w\/ Gym, Pool, near Fulton Market, by Blueground$
From $321 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 $321 per night (USD)
VRBO
$Mod West Loop 2BR w\/ Gym, Pool, W\/D, nr. Fulton Market, by Blueground$
From $215 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 $215 per night (USD)
Expedia

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