Chicago Rentals
From $1090 per night (USD)VRBO
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
- 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 $1090 per night (USD)VRBO
From $1090 per night (USD)Expedia
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
- 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 $1090 per night (USD)Expedia
From $1098 per night (USD)VRBO
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
- 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 $1098 per night (USD)VRBO
From $171 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 $171 per night (USD)Expedia
From $321 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 $321 per night (USD)VRBO
From $251 per night (USD)Expedia
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 $251 per night (USD)Expedia
From $310 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 $310 per night (USD)VRBO
From $427 per night (USD)Expedia
*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 $427 per night (USD)Expedia
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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 ...
Click For PricingExpedia
From $1128 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 2 Modern Units, Pets are Welcome!
- 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 $1128 per night (USD)VRBO
From $255 per night (USD)VRBO
Best Value, Quality Stay! Pet-Friendly Property, Close to Water Tower Chicago!
- 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 $255 per night (USD)VRBO
From $619 per night (USD)VRBO
Spacious Good-Value Accommodation! Pet-Friendly Property, 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 $619 per night (USD)VRBO
From $586 per night (USD)VRBO
A Place You'll Surely Enjoy! Near Chicago History Museum, 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 $586 per night (USD)VRBO
From $365 per night (USD)VRBO
Affordability Meets Comfort! Close to Water Tower Chicago, Pets Are Welcome!
- 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 $365 per night (USD)VRBO
From $268 per night (USD)VRBO
Always a Great Idea To Unwind! Pet-Friendly Property, 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 $268 per night (USD)VRBO
From $268 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 $268 per night (USD)VRBO
From $553 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 ...
From $553 per night (USD)VRBO
From $401 per night (USD)Expedia
Newly Revamped Home - For privacy lovers
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Big family? Group getaway? We’ve got more sleeping space than you’ll know what to do with. Try finding this much space a ...
From $401 per night (USD)Expedia
From $139 per night (USD)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 ...
From $139 per night (USD)VRBO
From $152 per night (USD)Expedia
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 $152 per night (USD)Expedia
From $234 per night (USD)VRBO
2-Bed 2-Bath Apt | close to UC w/ Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to the UC Commons, your Near West Side apartment just steps away from the United Center! Located minute ...
From $234 per night (USD)VRBO
From $1172 per night (USD)Expedia
The Grand Kimball Lodge, Logan Square, Sleeps 20
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 20
Summary: Welcome to The Grand Kimball Lodge — a one-of-a-kind experience that’s been featured in Architectural Digest's ...
From $1172 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 $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 $580 per night (USD)VRBO
St.Bens, Jacuzzi, EV Parking! 4 beds, Walk to Wrigley Field & Brown Line!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Looking for a spacious, stylish, and fully-equipped home in the heart of Chicago? Book your stay now and make this beau ...
From $580 per night (USD)VRBO
From $378 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 $378 per night (USD)VRBO
From $86 per night (USD)VRBO
Great Place
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
great place, have nice stuff, yadda yadda yadda, hkhbhhbbjjbhjbvghvghcfcggfcdxgnfgfcfgxdfxfchfdxfxfdxfgdxfxdxfxfxdxddddx ...
From $86 per night (USD)VRBO
From $186 per night (USD)Expedia
Charming 5 bedrooms 2 bath near Downtown Loop and Mc cormick Place, Museum
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 6
5 bed 2 full bathroom with 2,600 of living space. Property is located on a quiet street with long term ownership. Restau ...
From $186 per night (USD)Expedia
From $283 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, cafe ...
From $283 per night (USD)VRBO
From $368 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 $368 per night (USD)Expedia
From $168 per night (USD)VRBO
iKlektik House // Robin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Bright, Sunny and Stylish one bedroom, full kitchen, balcony over looking the backyard in West Town. Close to Wicker Par ...
From $168 per night (USD)VRBO
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 Near North with views over the city. It’ll be easy to s ...
From $164 per night (USD)Expedia
From $270 per night (USD)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 ...
From $270 per night (USD)VRBO
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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 l ...
Click For PricingExpedia
From $101 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 $101 per night (USD)VRBO
From $1116 per night (USD)VRBO
-Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Have fun with the whole family at this stylish place. Your family will be close to everything when you stay at this cent ...
From $1116 per night (USD)VRBO
From $662 per night (USD)VRBO
Spacious 5 BR / King Size Beds + Private Parking!
- Bedrooms:
- 2
- 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 $662 per night (USD)VRBO
From $3482 per night (USD)Expedia
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)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 $354 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 $354 per night (USD)Expedia
From $401 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 $401 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $209 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 Chicago Loop furnished one bedroom apa ...
From $209 per night (USD)VRBO
Click For PricingExpedia
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. ...
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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 Fulton Market District. It’ll be easy to simply show up ...
Click For PricingVRBO
From $704 per night (USD)Expedia
The Banksy-King Bed-Firepit-Rooftop-United Center
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
The Banksy, a modern 2-story duplex just 3 miles from downtown is ideal for large groups. Host your Bachelor / Bachelore ...
From $704 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
From $313 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 $313 per night (USD)Expedia
From $187 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 Near West Side. It’ll be easy to simply show up and sta ...
From $187 per night (USD)VRBO
From $187 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 $187 per night (USD)Expedia
Click For PricingVRBO
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 ...
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From $730 per night (USD)VRBO
Villa Noir Chicago Victorian home 7 min to downtown, museums, shops & the beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Villa Noir - an expertly designed vacation HOME fully equipped with everything you need for a most enjoyable ...
From $730 per night (USD)VRBO
From $222 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 apartment in River North with views over the city. It’ll be easy to ...
From $222 per night (USD)VRBO
From $755 per night (USD)Expedia
Luxury Loft Collection 903 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $755 per night (USD)Expedia
From $738 per night (USD)VRBO
Luxury Loft Collection 902 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $738 per night (USD)VRBO
From $122 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 Near West Side furnished one bedroom a ...
From $122 per night (USD)Expedia
From $163 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 Fulton Market District furnished one ...
From $163 per night (USD)VRBO
From $193 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 Near West Side. It’ll be easy to simply show up and sta ...
From $193 per night (USD)Expedia
From $185 per night (USD)VRBO
Cozy 2 Bedroom unit-15mins Dwtn!
- 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 $185 per night (USD)VRBO
From $243 per night (USD)Expedia
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 $243 per night (USD)Expedia
From $492 per night (USD)VRBO
McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
From $492 per night (USD)VRBO
From $1071 per night (USD)Expedia
Luxurious apartment McCormick Place 5 King bedrooms/3bath Suite for groups
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 1800 sq f Luxurious ...
From $1071 per night (USD)Expedia
From $341 per night (USD)VRBO
McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Private patio • Cit ...
From $341 per night (USD)VRBO
From $564 per night (USD)Expedia
Luxurious McCormick 3be/2ba Suite/up to 8 guests w optional parking/Gym/Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 KING size bedroo ...
From $564 per night (USD)Expedia
From $1063 per night (USD)VRBO
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 ...
From $1063 per night (USD)VRBO
From $902 per night (USD)Expedia
Luxurious McCormick 5 bed/4 bath Suite for up to 12 guests with optional parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Luxurious unit for ...
From $902 per night (USD)Expedia
From $547 per night (USD)VRBO
McCormick Place 6 twin beds + Sofa bed with Optional parking for up to 10 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 6 twin size beds + ...
From $547 per night (USD)VRBO
From $675 per night (USD)Expedia
Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Luxurious Modern Retreat with 1000 sqft Rooftop Welcome to the Monticello - our stunning modern new construction, desig ...
From $675 per night (USD)Expedia
From $257 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 $257 per night (USD)VRBO
From $133 per night (USD)Expedia
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 Near West Side furnished one bedroom a ...
From $133 per night (USD)Expedia
From $97 per night (USD)VRBO
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 Near West Side. It’ll be easy to simply show up and sta ...
From $97 per night (USD)VRBO
From $495 per night (USD)Expedia
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Bee's Knees - a vintage gem with a Hollywood-glam twist! This 4-BR Chicago bungalow home is the perfect getaw ...
From $495 per night (USD)Expedia
From $258 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 $258 per night (USD)VRBO
From $186 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 $186 per night (USD)VRBO
From $1285 per night (USD)VRBO
New home w/view & party deck - 2nd Floor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Prime Location: Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovat ...
From $1285 per night (USD)VRBO
From $1166 per night (USD)Expedia
3Bed/2Bath Wrigley home w/view & party deck 443 ft from Wrigley Field - 3rd Fl
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovated down to the s ...
From $1166 per night (USD)Expedia
From $317 per night (USD)VRBO
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 str ...
From $317 per night (USD)VRBO
From $246 per night (USD)Expedia
3 Bedroom Medical Center!
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $246 per night (USD)Expedia
From $91 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 $91 per night (USD)VRBO
From $85 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 $85 per night (USD)Expedia
From $83 per night (USD)VRBO
Sunny South Loop 1BR, nr Soldier Field, CTA Train & Park, 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 l ...
From $83 per night (USD)VRBO
From $352 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 $352 per night (USD)VRBO
From $98 per night (USD)VRBO
Stellar South Loop 1BR, near CTA Train, Sports & Parks, by blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop with high floor views over the city. It’ll b ...
From $98 per night (USD)VRBO
From $223 per night (USD)Expedia
Deluxe River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming River North furnished one bedroom ap ...
From $223 per night (USD)Expedia
From $156 per night (USD)VRBO
Wonderful Edgewater 1BR w/ Patio Deck & Gym, near lake, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach. It’ll be easy to simply show up and st ...
From $156 per night (USD)VRBO
From $94 per night (USD)Expedia
Cozy & Comfy 2 bedroom remodeled with plenty parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this beautifully remodeled fully furnished apartment for rent located on the south side of Chicago This 2-bed ...
From $94 per night (USD)Expedia
From $331 per night (USD)VRBO
2-bedroom apartment just 2 minutes drive to Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the heart of Chicago's vibrant North Center neighborhood in this charming 2-bedroom apartment. Situated just a ...
From $331 per night (USD)VRBO
From $278 per night (USD)Expedia
Cozy apartment near zoo, DePaul, Oz Park and much more!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful brownstone in the heart of Lincoln Park. 5 minute walk to Lincoln Park zoo, lakefront, variety of restaurants/ ...
From $278 per night (USD)Expedia
From $204 per night (USD)VRBO
Charming 4-bedroom apartment in delightful Chicago with central heat/AC, WiFi.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover this marvelous 4-bedroom gem in Chicago. Step into this cool apartment and be greeted by a pleasant ambiance th ...
From $204 per night (USD)VRBO
From $331 per night (USD)Expedia
Gold Coast/Downtown Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
New Listing! Freshly renovated Gold Coast hideaway provides the perfect escape from the nearby shopping and restaurant a ...
From $331 per night (USD)Expedia
From $458 per night (USD)VRBO
Chic and Spacious Bi-level 3BD in Bucktown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This one-of-a-kind condo in Bucktown is ready to host! The property features a hidden staircase leading down to the in-l ...
From $458 per night (USD)VRBO
From $216 per night (USD)Expedia
Cozy & Colorful garden unit in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Escape to our private 3 bedroom garden condo in trendy Logan Square. This urban retreat offers a cozy living space with ...
From $216 per night (USD)Expedia
From $102 per night (USD)VRBO
Lovely 2BR Gem w/ Outdoor Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover your perfect urban retreat in the heart of Chicago's trendy Logan Square/Avondale neighborhood. This beautiful ...
From $102 per night (USD)VRBO
From $204 per night (USD)Expedia
The Landmark; a comfy suite near McCormick Place
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the landmark. A cozy well appointed studio space in the heart of the historic Calumet/Giles Prairie district ...
From $204 per night (USD)Expedia
From $283 per night (USD)VRBO
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Penthouse Loft in Chicago. As avid travelers and frequent VRBO users, we've infused our home with inspira ...
From $283 per night (USD)VRBO
From $773 per night (USD)Expedia
6BR Chicago Gem: Prime, Safe, Family-Friendly Hub
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Experience Chicago in an unmatched setting: two apartments beautifully united into a grand 6-bedroom, 2-bathroom home in ...
From $773 per night (USD)Expedia
From $570 per night (USD)VRBO
Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 18
Gorgeous gem within 10 miles of Downtown, Airport, Lake Michigan, and United Center! About 15 miles from Wrigley Field ...
From $570 per night (USD)VRBO
From $364 per night (USD)Expedia
Charming 3-bedroom house in brilliant Chicago with WiFi, AC, plenty of sleeping.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover this fabulous 3-bedroom gem in Chicago. This wonderful house offers a cozy and inviting atmosphere that will ma ...
From $364 per night (USD)Expedia
From $243 per night (USD)VRBO
Spacious 4-bedroom apartment with AC and WiFi in terrific Chicago
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 14
Stay comfortably in Chicago at this 4-bedroom apartment. Marvelous and superb, this amazing property offers 4 queen beds ...
From $243 per night (USD)VRBO
From $255 per night (USD)VRBO
Charming 2-bedroom apartment in hip Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Chicago at this delightful apartment. With 2 bedrooms, including a king bed and a queen bed, this property is ...
From $255 per night (USD)VRBO