Chicago Rentals
- From $371 per night (USD)
VRBO
Downtown Penthouse Vintage Loft Pvt Balcony+Gym
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 7
Welcome to our Penthouse Loft in the heart of Downtown! Guests love our home because: -It's Unique! -High loft ceilings ...
From $371 per night (USD)VRBO
- From $879 per night (USD)
VRBO
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 $879 per night (USD)VRBO
- From $1019 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 $1019 per night (USD)VRBO
- From $954 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 $954 per night (USD)VRBO
- From $115 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 $115 per night (USD)VRBO
- From $223 per night (USD)
VRBO
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 $223 per night (USD)VRBO
- From $192 per night (USD)
VRBO
Logan Square 2 BR\/1 BA-modern, near METRA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome: Located on the first floor in a typical Chicago style 3 unit building built in 1898. There is one unit above. ...
From $192 per night (USD)VRBO
- From $228 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 $228 per night (USD)VRBO
- From $306 per night (USD)
VRBO
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 $306 per night (USD)VRBO
- From $335 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 $335 per night (USD)VRBO
- From $153 per night (USD)
VRBO
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 $153 per night (USD)VRBO
- From $156 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 $156 per night (USD)VRBO
- From $1294 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 $1294 per night (USD)VRBO
- From $279 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 $279 per night (USD)VRBO
- From $628 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 $628 per night (USD)VRBO
- From $628 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 $628 per night (USD)VRBO
- From $420 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 $420 per night (USD)VRBO
- From $352 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 $352 per night (USD)VRBO
- From $284 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 $284 per night (USD)VRBO
- From $750 per night (USD)
VRBO
Amazing City Get Away. Perfect for Entertaining!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this beautiful hidden gem in the Logan Square neighborhood. Our guests love this place because of the lofted ...
From $750 per night (USD)VRBO
- From $538 per night (USD)
VRBO
3B\/3BA Luxury Navy Pier Corner Sky Loft with Pool & Gym
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Perfectly located with the best of the city at your doorstep. This modern apartment is designed with a sweet co ...
From $538 per night (USD)VRBO
- From $614 per night (USD)
VRBO
3B\/2BA Captivating Corner Apartment w\/ Pier Views, Pool & Gym
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Perfectly located with the best of the city at your doorstep. This modern apartment is designed with a sweet co ...
From $614 per night (USD)VRBO
- From $633 per night (USD)
VRBO
3B\/3BA Distinguished Penthouse w\/ Panoranic Views, Pool & Gym
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Perfectly located with the best of the city at your doorstep. This modern apartment is designed with a sweet co ...
From $633 per night (USD)VRBO
- From $100 per night (USD)
VRBO
Culture Hotel \nA Cozy retreat steps away from Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Nice property laundry room inside of building beach and culture center-right across the street. Also there are plenty ...
From $100 per night (USD)VRBO
- From $553 per night (USD)
VRBO
Old Town 3bd 3ba Coach House, Garage Parking Incl by RedAwning
- 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 $553 per night (USD)VRBO
- Click For Pricing
VRBO
Enjoy Martinis on Milwaukee Ave and All the Nightlife Chicago Has to Offer! by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Two bedroom apartment in Logan Square, above an intimate boutique cocktail bar - You won't have to go far to enjoy Chica ...
Click For PricingVRBO
- From $307 per night (USD)
VRBO
Experience the Best Sites in Chicago & Rest Easy at the End of the Day by RedAwning
- 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 $307 per night (USD)VRBO
- From $361 per night (USD)
VRBO
2-Bedroom 2-Bath Apartment Close to the UC w\/ Free Off Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to the UC Commons, your Near West Side apartment just steps away from the United Center! Located minutes from Do ...
From $361 per night (USD)VRBO
- From $171 per night (USD)
VRBO
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 $171 per night (USD)VRBO
- From $120 per night (USD)
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 ...
From $120 per night (USD)VRBO
- From $191 per night (USD)
VRBO
Coach house in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the allure of Chicago's Jefferson Park in our historic coach house. This charming 2-bedroom, 1-bathroom gem fea ...
From $191 per night (USD)VRBO
- From $2648 per night (USD)
VRBO
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 $2648 per night (USD)VRBO
- From $195 per night (USD)
VRBO
Newly Revamped Home - For privacy lovers
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Discover your perfect escape in this newly constructed VRBO property. This chic entire front unit retreat offers 3 spaci ...
From $195 per night (USD)VRBO
- From $189 per night (USD)
VRBO
Newly Renovated Apartment! 10 Minutes From Dowtown And The Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the charm of our newly renovated Wicker Park Airbnb, nestled in the heart of Chicago. This stylish, cozy retr ...
From $189 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $80 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 $80 per night (USD)VRBO
- From $89 per night (USD)
VRBO
Chic Chicago Abode: Steps from Magnificent Mile!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $89 per night (USD)VRBO
- From $839 per night (USD)
VRBO
Large Apt with 2 Car Garage and EV Charger! Walk to Wrigley Field & Brown Line!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
- Garage with 2 spots and EV charger just for you! - 10 Minute walk to Irving Park Brown Line Station - Desirable North ...
From $839 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Wicker Park Duplex: 10 Min 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 $475 per night (USD)VRBO
- From $100 per night (USD)
VRBO
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 $100 per night (USD)VRBO
- From $401 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 $401 per night (USD)VRBO
- From $71 per night (USD)
VRBO
Great Place
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
great place, have nice stuff, yadda yadda yadda, hkhbhhbbjjbhjbvghvghcfcggfcdxgnfgfcfgxdfxfchfdxfxfdxfgdxfxdxfxfxdxddddx ...
From $71 per night (USD)VRBO
- From $171 per night (USD)
VRBO
Ideal & Spacious 1BR Apt: Fully Furnished!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your stylish oasis in the heart of Chicago! This gem offers a perfect blend of modern comfort and urban conve ...
From $171 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Newly Designed 3bd In Heart of Ukrainian Village by RedAwning
- 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 $399 per night (USD)VRBO
- From $259 per night (USD)
VRBO
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 $259 per night (USD)VRBO
- From $231 per night (USD)
VRBO
Quiet, relaxing 4 bed, 2 bath, 10 mins to Lake Michigan
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Relax with the whole family at this peaceful place to stay in Chicago Pill Hill area . Its a warm and lovely 4bd, 2 ba ...
From $231 per night (USD)VRBO
- From $145 per night (USD)
VRBO
Archways at the Lincoln Park Zoo 2bed\/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About this space The remains of Art Deco arches lend character and historic context to an apartment in a former hotel fr ...
From $145 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Luxury 10PERSON Townhome near Beach and Golf Course 10 Min DT, Private Rooftop!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
HUGE newly constructed townhome with open concept layout with large, updated kitchen and dining room area. Home features ...
From $225 per night (USD)VRBO
- From $149 per night (USD)
VRBO
5 bed 2 full Bath in Avalon park near high park South shore Chatham SouthLoop
- 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 $149 per night (USD)VRBO
- From $170 per night (USD)
VRBO
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 $170 per night (USD)VRBO
- Click For Pricing
VRBO
Stylish Streeterville 2BR w\/ Lounge & Pool, nr Riverwalk, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Streeterville furnished two-bedroom ap ...
Click For PricingVRBO
- From $106 per night (USD)
VRBO
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 South Loop apartment. It’ll be easy to simply show up and start livi ...
From $106 per night (USD)VRBO
- From $148 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 $148 per night (USD)VRBO
- Click For Pricing
VRBO
17th-Floor Central Chicago Condo w\/ Skyline Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Make your home away from home in the heart of the Windy City at this Chicago vacation rental. This 2-bed, 2-bath condo i ...
Click For PricingVRBO
- From $149 per night (USD)
VRBO
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 River North apartment with views over the city. It’ll be easy to si ...
From $149 per night (USD)VRBO
- From $500 per night (USD)
VRBO
-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 $500 per night (USD)VRBO
- From $125 per night (USD)
VRBO
Updated Vintage 1883 firehouse 2 br 1 bath cozy quiet clean fully furnished apt
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Very quiet clean awesome two bedroom apt in a great part of chicago. This was once a horse and buggy carriage interim f ...
From $125 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Welcome to east 93rd
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Make some memories at this unique and family-friendly place. Key Features: Cozy 3-bedroom, 1-bathroom floor Spacious li ...
From $180 per night (USD)VRBO
- From $665 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 $665 per night (USD)VRBO
- Click For Pricing
VRBO
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 PricingVRBO
- From $3150 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 $3150 per night (USD)VRBO
- From $124 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 $124 per night (USD)VRBO
- From $182 per night (USD)
VRBO
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 $182 per night (USD)VRBO
- From $65 per night (USD)
VRBO
Fully Furnished Vintage 1bed\/1bath apartment in Jefferson Park!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Vintage Chicago large 1 bedroom unit! Quiet and safe neighborhood. Close to public transportation and major expressways ...
From $65 per night (USD)VRBO
- From $389 per night (USD)
VRBO
Luxury Modern Condo in Chicago Close to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our spacious and luxurious condo located in the vibrant city of Chicago! This magnificent newly constructed ...
From $389 per night (USD)VRBO
- From $47 per night (USD)
VRBO
Private \"Room C\" within shared space in Woodlawn,15 minutes from everything!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Historic Chicago fully furnished room for rent within a 4 bed/2bed shared space in Woodlawn, 15 minute away from everyth ...
From $47 per night (USD)VRBO
- From $376 per night (USD)
VRBO
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 $376 per night (USD)VRBO
- From $427 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 $427 per night (USD)VRBO
- From $119 per night (USD)
VRBO
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 $119 per night (USD)VRBO
- From $275 per night (USD)
VRBO
wicker park large apartment perfect for families
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Lots of room- three level unit. 2 outdoor patios at rear. Neighborhood is lively and close to some of the best bars and ...
From $275 per night (USD)VRBO
- From $381 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 $381 per night (USD)VRBO
- From $397 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 $397 per night (USD)VRBO
- From $125 per night (USD)
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 ...
From $125 per night (USD)VRBO
- From $309 per night (USD)
VRBO
Historic Chicago Home < 1 Mi to Lake Michigan
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This spacious Chicago home, built in 1893, boasts unique charm in every detail! The 3-bedroom, 2.5-bathroom vacation ren ...
From $309 per night (USD)VRBO
- From $200 per night (USD)
VRBO
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. ...
From $200 per night (USD)VRBO
- From $182 per night (USD)
VRBO
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 $182 per night (USD)VRBO
- From $295 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 West Loop apartment. It’ll be easy to simply show up and start livin ...
From $295 per night (USD)VRBO
- From $1139 per night (USD)
VRBO
Downtown Penthouse 5bd\/4ba VIEWS, Parking, Gym
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to our Two 2-Story Downtown Penthouses (Combined Units) with Million Dollar Views. Guests love staying with us ...
From $1139 per night (USD)VRBO
- From $219 per night (USD)
VRBO
Spacious Chicago Apartment with Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Forget your worries in this spacious and serene space. With three bedrooms, and a ton of space, you will enjoy every min ...
From $219 per night (USD)VRBO
- From $100 per night (USD)
VRBO
Windy City 2BD: Mins from Downtown & Laundry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Prime Location 2BR, just about 3 miles from Downtown Chicago Loop. This unit is centrally located in one of Chicago's mo ...
From $100 per night (USD)VRBO
- From $40 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 $40 per night (USD)VRBO
- From $806 per night (USD)
VRBO
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 $806 per night (USD)VRBO
- From $141 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 West Loop apartment. It’ll be easy to simply show up and start livin ...
From $141 per night (USD)VRBO
- From $566 per night (USD)
VRBO
The Banksy 4bd Duplex - King bed - walk to United Center, close to downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
United Center Greystone, modern 4 bedroom, 1 king bed, 3 queen , 2 bath 2 level duplex apartment with awesome outdoor li ...
From $566 per night (USD)VRBO
- From $130 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 $130 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Luxe living awaits in our newly built condo in the artsy Bronzeville district
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Step into luxury with our newly constructed, entire condo located in the heart of the vibrant Bronzeville Art District. ...
From $350 per night (USD)VRBO
- From $103 per night (USD)
VRBO
Chic 2BR Haven: Minutes from Downtown & Medical District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to your tranquil urban oasis in the vibrant heart of Chicago, IL! Nestled on a serene block near Douglas Park in ...
From $103 per night (USD)VRBO
- From $102 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 $102 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Chicago BIg House
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 12
Bring the whole family or a group of friends to this wonderful spacious home on Chicago's northwest side. This amazing n ...
From $425 per night (USD)VRBO
- From $550 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 $550 per night (USD)VRBO
- From $129 per night (USD)
VRBO
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 River North apartment. It’ll be easy to simply show up and start liv ...
From $129 per night (USD)VRBO
- From $1090 per night (USD)
VRBO
7B\/3BA Private Unit in Lincoln Park near Wrigley
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 14
Summary: Discover the vibrant heart of Chicago from our Amazing Fully Furnished 7BR Home. Located in the city's most pop ...
From $1090 per night (USD)VRBO
- From $235 per night (USD)
VRBO
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 $235 per night (USD)VRBO
- From $253 per night (USD)
VRBO
A Home Away From Home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the allure of this newly renovated Georgian house. Boasting ample space for family enjoyment. With its close pr ...
From $253 per night (USD)VRBO
- From $367 per night (USD)
VRBO
River North Central Home With Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Enjoy a stylish experience at this centrally-located home in Chicago's River West neighborhood. Relax indoors a ...
From $367 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Chic River North Condo 2BR 2BA with Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to our riverfront oasis nestled in the vibrant heart of Chicago's trendy River North neighborhood! Thi ...
From $350 per night (USD)VRBO
- From $234 per night (USD)
VRBO
Fulton market \/ Noble Square FREE parking, Laundry, 2.5 miles to Mag Mile!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
BEST neighborhood in Chicago. This is the 1st real neighborhood west of all the high-rises, walking distance to restaura ...
From $234 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Unique Chicago Penthouse Loft - Amazing Deal & Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ideal for a Chicago Get-Away, business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (no ...
From $400 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Inactive listing
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Delete this account no longer listing this unitaahdjdjdhdbrhdjdntnrgwgdhfjfkrjebdhehehdbfjfheheerehdbdbdvdjfkgjdbdvdhfjt ...
From $360 per night (USD)VRBO