Chicago, Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Chicago, Illinois on RentalSaver.com!

Chicago Rentals

From $251 per night (USD)
VRBO
Downtown Penthouse Vintage Loft Pvt Balcony+Gym
Bedrooms:
2
Bathrooms:
1
Sleeps:
7
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Welcome to our Penthouse Loft in th ...
From $251 per night (USD)
VRBO
From $1072 per night (USD)
Expedia
Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Located inside one of the iconic Wrigley Rooftops, and just a few steps away from Wrigley Field, this apartment offers a ...
From $1072 per night (USD)
Expedia
From $1072 per night (USD)
VRBO
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)
VRBO
From $1072 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 $1072 per night (USD)
Expedia
From $164 per night (USD)
VRBO
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)
VRBO
From $248 per night (USD)
Expedia
Lincoln Park Light Filled Loft
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience this unique Lincoln Park loft where you’ll love the open concept space, the floor to ceiling windows, & the c ...
From $248 per night (USD)
Expedia
From $195 per night (USD)
VRBO
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Be sure to check out the VIDEO tour push the arrow on the third photo. Happy to accommodate same day reservations pl ...
From $195 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Contemporary 2BR Flat Right Next to Wrigley Field & Transit ❤️ Cubs!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Experience city life; Located in Wrigley! Feel like a local! We're experienced! we've hosted more than 1000 reservati ...
From $256 per night (USD)
Expedia
From $600 per night (USD)
VRBO
*Comfortable & Spacious Home Close to Downtown*
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
We are Airbnb Superhosts and have been on the platform since 2016. This is a Comfortable & Spacious beautifully furnish ...
From $600 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Cozy Lakeview apartment near Train Station
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Apartment is located in the charming Lakeview neighborhood steps away from the brown line train station, known for it's ...
From $172 per night (USD)
Expedia
$Chic West Loop 2BR w\/ Theater & Gym, nr Restaurant Row, by Blueground$
From $143 per night (USD)
VRBO
Chic West Loop 2BR w\/ Theater & Gym, nr Restaurant Row, by Blueground
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this stylish two bedroom Blueground apartment. You’ll love coming ...
From $143 per night (USD)
VRBO
$Your Home Away From Home! 2 Modern Units, Pets are Welcome, w\/ Pool!$
From $1201 per night (USD)
VRBO
Your Home Away From Home! 2 Modern Units, Pets are Welcome, w\/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $1201 per night (USD)
VRBO
$Best Value, Quality Stay! Pet-Friendly, Close to Water Tower Chicago, w\/ Pool!$
From $209 per night (USD)
VRBO
Best Value, Quality Stay! Pet-Friendly, Close to Water Tower Chicago, w\/ Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $209 per night (USD)
VRBO
$Spacious Good-Value Accommodation! w\/ Pool, Pet-Friendly, Near Willis Tower!$
From $609 per night (USD)
VRBO
Spacious Good-Value Accommodation! w\/ Pool, Pet-Friendly, Near Willis Tower!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $609 per night (USD)
VRBO
$A Place You'll Surely Enjoy! Near Chicago History Museum, w\/ Pool, Pet-Friendly!$
From $608 per night (USD)
VRBO
A Place You'll Surely Enjoy! Near Chicago History Museum, w\/ Pool, Pet-Friendly!
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $608 per night (USD)
VRBO
$Affordability Meets Comfort! Close to Water Tower Chicago, w\/ Swimming Pool!$
From $383 per night (USD)
VRBO
Affordability Meets Comfort! Close to Water Tower Chicago, w\/ Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $383 per night (USD)
VRBO
$Always a Great Idea To Unwind! Pet-Friendly, w\/ Pool, Near Marina City!$
From $243 per night (USD)
VRBO
Always a Great Idea To Unwind! Pet-Friendly, w\/ Pool, Near Marina City!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $243 per night (USD)
VRBO
From $209 per night (USD)
VRBO
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $209 per night (USD)
VRBO
From $313 per night (USD)
VRBO
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Experience the charm of Old Town in our spacious 3-bedroom coach house! This comfortable oasis offers a fully equipped k ...
From $313 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Experience the Best Sites in Chicago & Rest Easy at the End of the Day by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, La ...
From $193 per night (USD)
Expedia
$2-Bed 2-Bath Apt | close to UC w\/ Free Parking$
From $175 per night (USD)
VRBO
2-Bed 2-Bath Apt | close to UC w\/ Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the UC Commons, your Near West Side apartment just steps away from the United Center! Located minutes from Do ...
From $175 per night (USD)
VRBO
$Logan Square Monthly Apartment\n$
From $113 per night (USD)
Expedia
Logan Square Monthly Apartment\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The apartment features one private bedroom. In addition, there's an open-concept sleeping area, which allows for flexibi ...
From $113 per night (USD)
Expedia
Click For Pricing
VRBO
Trendy 2 bdrm near McCormick Place & Wintrust Arena
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled bet ...
Click For Pricing
VRBO
From $1046 per night (USD)
Expedia
The Grand Kimball Lodge, Logan Square, Sleeps 20
Bedrooms:
4
Bathrooms:
5
Sleeps:
20
The Grand Kimball Lodge is an award winning property filled with enormous windows, a large, open concept layout, and Wes ...
From $1046 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Newly Revamped Home - For privacy lovers
Bedrooms:
1
Bathrooms:
2
Sleeps:
13
Total of 8beds plus kids bunk bed when the front and back unit are combined. Please read all the description. This is a ...
From $362 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Lakeview Lux - Apt #2
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $156 per night (USD)
Expedia
From $170 per night (USD)
VRBO
Lakeview Lux - Apt #1
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $170 per night (USD)
VRBO
From $113 per night (USD)
Expedia
Charming Coach House in Chicago's Hot Wicker Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wicker Park is known as Chicago's trendy enclave. Chicagoans and tourists alike are drawn to this hot spot neighborhood. ...
From $113 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Belmont & Racine - Walk to Wrigley Field, Southport Corridor, and Belmont CTA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Belmont & Racine, your getaway location in the heart of the Lakeview neighborhood of Chicago, Illinois! Short ...
From $272 per night (USD)
VRBO
From $93 per night (USD)
Expedia
Chic Chicago Abode: Steps from Magnificent Mile!
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
Discover the best of the Windy City with a stay at this charming 3-bedroom, 1.5-bathroom home. Immerse yourself in the v ...
From $93 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Luxury Chicago 2 Story Condo: 10 Mins to Downtown
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Experience luxury in our 2 bedroom (3 bed) duplex down, spread over 2 levels, our home offers over 1800+ sq ft of room. ...
From $231 per night (USD)
VRBO
From $86 per night (USD)
Expedia
Great Place
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
great place, have nice stuff, yadda yadda yadda, hkhbhhbbjjbhjbvghvghcfcggfcdxgnfgfcfgxdfxfchfdxfxfdxfgdxfxdxfxfxdxddddx ...
From $86 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Newly Designed 3bd In Heart of Ukrainian Village by AllSet Turnover
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover the charm of Ukrainian Village in my beautifully designed home just steps from award winning restaurants, cafes ...
From $307 per night (USD)
VRBO
$Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR\/2BA Apartment in Chicago$
From $254 per night (USD)
Expedia
Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR\/2BA Apartment in Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
"Your Chicago Adventure Begins Here: Modern 3BR/2BA Haven, Just 10 Minutes from Downtown! Get ready to experience the b ...
From $254 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Cozy 5 bedrooms 2 bath near downtown loop and mcCormick Place
Bedrooms:
2
Bathrooms:
6
Sleeps:
6
5 bed 2 full bathroom with 2300sqft of living space. Property is located on a quiet street with long time ownership. Res ...
From $169 per night (USD)
VRBO
$iKlektik House \/\/ Robin$
From $161 per night (USD)
Expedia
iKlektik House \/\/ Robin
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Bright, Sunny and Stylish one bedroom, full kitchen, balcony over looking the backyard in West Town. Close to Wicker Par ...
From $161 per night (USD)
Expedia
From $91 per night (USD)
VRBO
3 bedrooms In the Windy City
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Anything you need, we have it! Anything you need, we have it! Anything you need, we have it! Anything you need, we have ...
From $91 per night (USD)
VRBO
From $1462 per night (USD)
Expedia
-Lovely 5 BedRoom Unit in Uptown
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Have fun with the whole family at this stylish place. Your family will be close to everything when you stay at this cent ...
From $1462 per night (USD)
Expedia
$Stylish Streeterville 2BR w\/ Lounge & Pool, nr Riverwalk, by Blueground$
From $270 per night (USD)
VRBO
Stylish Streeterville 2BR w\/ Lounge & Pool, nr Riverwalk, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Streeterville furnished two bedroom ap ...
From $270 per night (USD)
VRBO
$Great South Loop 1BR w\/ Games & Pool, nr Park & Train, by Blueground$
From $142 per night (USD)
Expedia
Great South Loop 1BR w\/ Games & Pool, nr Park & Train, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in South Loop. . It’ll be easy to simply show up and start ...
From $142 per night (USD)
Expedia
$Upscale Streeterville Jr 1BR w\/ Gym, nr Magnificent Mile, by Blueground$
From $127 per night (USD)
VRBO
Upscale Streeterville Jr 1BR w\/ Gym, nr Magnificent Mile, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
From $127 per night (USD)
VRBO
$Upscale River North 1BR w\/ Coffee Shop & Gym, nr Lake, by Blueground$
From $164 per night (USD)
Expedia
Upscale River North 1BR w\/ Coffee Shop & Gym, nr Lake, 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 $164 per night (USD)
Expedia
$Spacious 5 BR \/ King Size Beds + Private Parking!$
From $476 per night (USD)
VRBO
Spacious 5 BR \/ King Size Beds + Private Parking!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Discover Chicago from our cozy home! Just .5 mile from the Green Line CTA station, explore downtown with ease. 3 minute ...
From $476 per night (USD)
VRBO
Click For Pricing
Expedia
Wicker Parks, Designers Dream, on-trend 2 Bdrm
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
About this space Wicker Parks, Designers Dream is just that. As a facet of Red Robin Rentals property portfolio, you are ...
Click For Pricing
Expedia
$Vintage Chicago Gem: The Rockwell Retreat\n$
From $3482 per night (USD)
VRBO
Vintage Chicago Gem: The Rockwell Retreat\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
1
Discover your oasis in the heart of the city at our light-filled and lush apartment. Indulge in the warm and bright natu ...
From $3482 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Relaxing 2BR Apartment in Lively West Rogers Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Listing Description Welcome to this beautiful two-bed, one-bath apartment in the heart of West Rogers Park! Perfectly l ...
From $223 per night (USD)
Expedia
From $139 per night (USD)
VRBO
Apartment in Historic Lakeview Mansion - Best Location for Vacationers!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This 1902 home was completely renovated into 16 apartments in 2022. These brand new luxury apartments feature in unit la ...
From $139 per night (USD)
VRBO
From $381 per night (USD)
Expedia
3BD West Town Gem: Explore the Windy City in Style
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our stylish 3-bed, 2-bath Condo in the heart of Chicago's vibrant West Town. Designed for your comfort, it's ...
From $381 per night (USD)
Expedia
$Belmont Pleasures - hot tub \/ arcade gaming room$
From $479 per night (USD)
VRBO
Belmont Pleasures - hot tub \/ arcade gaming room
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
About this space Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come hav ...
From $479 per night (USD)
VRBO
$Trendy Loop Jr 1BR w\/ Game Room, nr Park & Riverwalk, by Blueground$
From $116 per night (USD)
Expedia
Trendy Loop Jr 1BR w\/ Game Room, nr Park & Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty The Loop furnished one bedroom apartme ...
From $116 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Sonder Jewelers Row | 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 $174 per night (USD)
VRBO
From $217 per night (USD)
VRBO
Sonder The Plymouth | One-Bedroom Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $217 per night (USD)
VRBO
Click For Pricing
VRBO
Gorgeous two Bedroom Unit-15mins to Downtown!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful two bedroom gem lodged in the heart of Bronzeville,5min drive from McCormick and IIT. Ideal location for a qui ...
Click For Pricing
VRBO
$Bucktown Apartment near all amazing restaurants, shops and bar\/lounges$
Click For Pricing
Expedia
Bucktown Apartment near all amazing restaurants, shops and bar\/lounges
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Recently renovated apartment in a two-story building. Sits right above our family-owned and operated chicken restaurant. ...
Click For Pricing
Expedia
$Cosy room near medical district w\/ private balcony$
From $61 per night (USD)
VRBO
Cosy room near medical district w\/ private balcony
Bedrooms:
2
Bathrooms:
1
Sleeps:
1
Welcome to our recently renovated duplex apartment, offering an ideal blend of modern comforts, such as central air/heat ...
From $61 per night (USD)
VRBO
From $983 per night (USD)
Expedia
Elegant private oasis in Ukrainian Village
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Elegant and Beautiful 5 bedroom / 3.5 bathroom single family house on a quiet residential neighborhood street of Ukraini ...
From $983 per night (USD)
Expedia
$Exquisite West Loop Jr 1BR w\/ Gym & Rooftop, nr Union Park, by Blueground$
From $148 per night (USD)
VRBO
Exquisite West Loop Jr 1BR w\/ Gym & Rooftop, nr Union Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in West Loop. . It’ll be easy to simply show up and start ...
From $148 per night (USD)
VRBO
From $438 per night (USD)
Expedia
The Banksy-King Bed-Firepit-Rooftop-United Center
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
The Banksy, a modern 2-story duplex just 3 miles from downtown is ideal for large groups. Host your Bachelor / Bachelore ...
From $438 per night (USD)
Expedia
From $148 per night (USD)
VRBO
Spacious 2BR, this hidden gem combines vintage allure with urban flair!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the charm of The Maestro, an amazing 2-bedroom, 1-bath apartment nestled within a stunning 1920’s era Chicago b ...
From $148 per night (USD)
VRBO
$Fabulous West Loop 2BR w\/ Rooftop & Dog Wash, nr L, by Blueground$
From $242 per night (USD)
Expedia
Fabulous West Loop 2BR w\/ Rooftop & Dog Wash, nr L, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this sophisticated two bedroom Blueground apartment. You’ll love c ...
From $242 per night (USD)
Expedia
$Charming West Loop 2BR w\/ Gym & Rooftop, nr Union Park, by Blueground$
From $217 per night (USD)
VRBO
Charming West Loop 2BR w\/ Gym & Rooftop, nr Union Park, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in West Loop. . It’ll be easy to simply show up and start ...
From $217 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Chic 2BR Haven: Minutes from Downtown & Medical District
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Welcome to your tranquil urban oasis in the vibrant heart of Chicago, IL! Nestled on a serene block near Douglas Park in ...
From $177 per night (USD)
Expedia
$Classic West Loop 1BR w\/ Gym, near Fulton Market & I-90, by Blueground$
From $118 per night (USD)
VRBO
Classic West Loop 1BR w\/ Gym, near Fulton Market & I-90, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $118 per night (USD)
VRBO
From $757 per night (USD)
Expedia
Chicago Big House Central
Bedrooms:
3
Bathrooms:
7
Sleeps:
12
This listing is NOT new, although the rental platforms may show it new. This "whole house" rental is a combination of tw ...
From $757 per night (USD)
Expedia
From $694 per night (USD)
VRBO
Villa Noir Chicago Victorian home 7 min to downtown, museums, shops & the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to Villa Noir - an expertly designed vacation HOME fully equipped with everything you need for a most enjoyable ...
From $694 per night (USD)
VRBO
$Trendy River North 1BR w\/ Pool & Gym, near Riverwalk, by Blueground$
From $111 per night (USD)
Expedia
Trendy River North 1BR w\/ Pool & Gym, near Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in River North. . It’ll be easy to simply show up and star ...
From $111 per night (USD)
Expedia
From $236 per night (USD)
VRBO
2 bedroom Pastel Loft 1 mi from Lake Michigan!
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Welcome to our chic and colorful lofted apartment in the lovely neighborhood of Roger’s Park in Chicago! It's convenient ...
From $236 per night (USD)
VRBO
Click For Pricing
Expedia
Trendy Two Bedroom Unit-15mins to downtown!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Trendy two unit apartment nested between South Loop and Bronzeville. The unit is in close proximity to McCormick,Winturs ...
Click For Pricing
Expedia
$Luxurious apartment McCormick Place 5 King bedrooms\/3bath Suite for groups$
Click For Pricing
VRBO
Luxurious apartment McCormick Place 5 King bedrooms\/3bath Suite for groups
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 1800 sq f Luxurious ...
Click For Pricing
VRBO
$McCormick Patio skyline view 2b\/2b with optional Parking\/sleep 6$
Click For Pricing
Expedia
McCormick Patio skyline view 2b\/2b with optional Parking\/sleep 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Private patio • Cit ...
Click For Pricing
Expedia
$Luxurious McCormick 3be\/2ba Suite\/up to 8 guests w optional parking\/Gym\/Patio$
Click For Pricing
VRBO
Luxurious McCormick 3be\/2ba Suite\/up to 8 guests w optional parking\/Gym\/Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 KING size bedroo ...
Click For Pricing
VRBO
$Luxurious McCormick 6 bed\/4 bath Suite for up to 12 guests w Jacuzzi\/Opt parking$
Click For Pricing
Expedia
Luxurious McCormick 6 bed\/4 bath Suite for up to 12 guests w Jacuzzi\/Opt parking
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Jacuzzi in the unit • 2609 sq f Luxurious unit ...
Click For Pricing
Expedia
$Luxurious McCormick 5 bed\/4 bath Suite for up to 12 guests with optional parking$
Click For Pricing
VRBO
Luxurious McCormick 5 bed\/4 bath Suite for up to 12 guests with optional parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Luxurious unit for ...
Click For Pricing
VRBO
Click For Pricing
Expedia
McCormick Place 6 twin beds + Sofa bed with Optional parking for up to 10 guests
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 6 twin size beds + ...
Click For Pricing
Expedia
$South Shore Retreat 5 bedrooms\/entertainment$
From $189 per night (USD)
VRBO
South Shore Retreat 5 bedrooms\/entertainment
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
This stylish place to stay is perfect for group or work trips. Enjoy a five minute stroll to Lake Michigan or drive five ...
From $189 per night (USD)
VRBO
From $660 per night (USD)
Expedia
Luxury Loft Collection 903 - Terrace - River North
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $660 per night (USD)
Expedia
From $653 per night (USD)
VRBO
Luxury Loft Collection 902 - Terrace - River North
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $653 per night (USD)
VRBO
$Deluxe West Loop 1BR w\/ Rooftop, Gym & Grills, nr Park, by Blueground$
From $146 per night (USD)
Expedia
Deluxe West Loop 1BR w\/ Rooftop, Gym & Grills, nr Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this cheery West Loop furnished one bedroom apartm ...
From $146 per night (USD)
Expedia
$Ideal West Loop Jr 1BR w\/ Rooftop, Gym & Grills, nr Park, by Blueground$
From $148 per night (USD)
VRBO
Ideal West Loop Jr 1BR w\/ Rooftop, Gym & Grills, nr Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish West Loop furnished one bedroom apart ...
From $148 per night (USD)
VRBO
$Delightful West Loop 1BR w\/ Gym, near Fulton Market & I-90, by Blueground$
From $136 per night (USD)
Expedia
Delightful West Loop 1BR w\/ Gym, near Fulton Market & I-90, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in West Loop. . It’ll be easy to simply show up and start ...
From $136 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Cozy 2 Bedroom unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Trendy two unit apartment nested between South Loop and Bronzeville. The unit is in close proximity to McCormick,Winturs ...
From $178 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Chicago Vacation Rental, 19 Mi to Downtown Area!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Explore the vibrant city of Chicago from the comfort of this 4-bedroom, 2-bath vacation rental. Located just minutes awa ...
From $192 per night (USD)
Expedia
$McCormick 3B\/2Ba Family Oasis up to 8 guests with Parking-Optional\/Gym\/Patio$
Click For Pricing
VRBO
McCormick 3B\/2Ba Family Oasis up to 8 guests with Parking-Optional\/Gym\/Patio
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
Click For Pricing
VRBO
$Luxury Chic Condo Near Hot Attractions w\/FastWi-Fi$
From $229 per night (USD)
Expedia
Luxury Chic Condo Near Hot Attractions w\/FastWi-Fi
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to this spacious "Home Away from Home" fully equipped with all you need for your comfort & enjoyment. Each of th ...
From $229 per night (USD)
Expedia
$Divine West Loop 1BR w\/ Gym & Rooftop, nr Union Park, by Blueground$
From $135 per night (USD)
VRBO
Divine West Loop 1BR w\/ Gym & Rooftop, nr Union Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty West Loop furnished one bedroom apartm ...
From $135 per night (USD)
VRBO
$Dreamy West Loop 1BR w\/ Rooftop & Dog Wash, nr L, by Blueground$
From $142 per night (USD)
Expedia
Dreamy West Loop 1BR w\/ Rooftop & Dog Wash, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in West Loop. . It’ll be easy to simply show up and start ...
From $142 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Chicago New 2BR Home w 3 Beds and HighSpeed Internet
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Enjoy a stylish experience at this centrally-located home in the eccentric Wicker Park neighborhood of Chicago. ...
From $217 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to Bee's Knees - a blast from the past with a hollywood-glam twist. This 4 BR home is the perfect getaway for a ...
From $362 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Each elegantly designed room at the hotel comes with plush bedding and modern amenities to ensure a comfortable experien ...
From $190 per night (USD)
VRBO
From $206 per night (USD)
VRBO
Cozy Spacious 3br
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Nice and Spacious Cozy apartment nestled in the heart of chicago, top floor apt. With Double ovens when cooking for a ni ...
From $206 per night (USD)
VRBO
$New home w\/view & party deck - 2nd Floor$
From $1227 per night (USD)
VRBO
New home w\/view & party deck - 2nd Floor
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Prime Location: Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovat ...
From $1227 per night (USD)
VRBO
From $554 per night (USD)
Expedia
Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage
Bedrooms:
6
Bathrooms:
5
Sleeps:
16
Luxurious Modern Retreat with 1000 sqft Rooftop Welcome to the Monticello - our stunning modern new construction, desig ...
From $554 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Downtown Delight: Chic Stay near Chicago Theater! Pets are welcome!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Each elegantly designed room at the hotel comes with plush bedding and modern amenities to ensure a comfortable experien ...
From $177 per night (USD)
VRBO
From $324 per night (USD)
VRBO
Newly remodeled 3 bedroom apt, a hidden gem 20 min to almost anyplace in Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Keep it simple at this peaceful apartment and it’s centrally-located place to almost Everything. Newly renovated 3 bedr ...
From $324 per night (USD)
VRBO
$3 Bed Wrigley home w\/view & party deck - 3rd Fl$
From $1198 per night (USD)
VRBO
3 Bed Wrigley home w\/view & party deck - 3rd Fl
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovated down to the s ...
From $1198 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined stre ...
From $239 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Modern Bungalow near the beach! 20 minutes to downtown!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
This stylish home is perfect for group trips. With only 26 minutes to Midway airport and less than 10 minutes to the nea ...
From $335 per night (USD)
VRBO
From $195 per night (USD)
Expedia
3 Bedroom Medical Center!
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Summary: A couple house off the popular Taylor St which has plenty of restaurants and bars! The Space: 3 Bedrooms 1 Ful ...
From $195 per night (USD)
Expedia
$Striking South Loop 1BR w\/ Rooftop, walk to Grant Park, by Blueground$
From $159 per night (USD)
VRBO
Striking South Loop 1BR w\/ Rooftop, walk to Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated South Loop furnished one bedroo ...
From $159 per night (USD)
VRBO
$Sweet South Loop 1BR w\/ Rooftop, nr Grant Park & Museums, by Blueground$
From $144 per night (USD)
Expedia
Sweet South Loop 1BR w\/ Rooftop, nr Grant Park & Museums, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated South Loop furnished one bedroo ...
From $144 per night (USD)
Expedia

Search Your Destination Now!

Chicago Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals