Chicago Rentals
- From $84 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 $84 per night (USD)VRBO
- From $517 per night (USD)
Expedia
Newly Designed 3bd In Heart of Ukrainian Village
- 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 $517 per night (USD)Expedia
- From $256 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 $256 per night (USD)VRBO
- From $234 per night (USD)
Expedia
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 $234 per night (USD)Expedia
- From $144 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 $144 per night (USD)VRBO
- From $97 per night (USD)
Expedia
Modern 2BR Furnished Apt w\/In-Unit Laundry!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect retreat nestled in the heart of Chicago. Our fully furnished 2-bedroom apartment is a stylish fu ...
From $97 per night (USD)Expedia
- 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 $177 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 $177 per night (USD)Expedia
- 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 $124 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 $124 per night (USD)Expedia
- From $152 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 $152 per night (USD)VRBO
- From $115 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 $115 per night (USD)Expedia
- From $137 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 $137 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 $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 $595 per night (USD)
Expedia
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 $595 per night (USD)Expedia
- 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)
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 $3150 per night (USD)Expedia
- 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 $280 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 $280 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
About this space This isn't just a home I'm listing for profit, its a labor of love, years of sacrifice and sentimental ...
From $400 per night (USD)VRBO
- From $65 per night (USD)
Expedia
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)Expedia
- 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
- Click For Pricing
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 ...
Click For PricingVRBO
- From $409 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 $409 per night (USD)VRBO
- From $85 per night (USD)
Expedia
Chicago Hi-Rise Lakeside Living in Spacious Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Very quiet, circa 1928, elegant building with doorman, owned and decorated by an art collector. Walking distance from: t ...
From $85 per night (USD)Expedia
- From $170 per night (USD)
VRBO
Modern 2-Bdrm Condo - Private Patio - In Unit Laundry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
If you're seeking a modern retreat in a dynamic neighborhood, this 2-bedroom, this top floor condo with a furnished priv ...
From $170 per night (USD)VRBO
- From $427 per night (USD)
Expedia
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)Expedia
- 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 $480 per night (USD)
Expedia
Fantastic 4 BR 2BR, Minutes from Down Town Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our incredible oasis in the vibrant neighborhood of Avondale/Logan Square, Chicago! This stunning 4-bedroom, ...
From $480 per night (USD)Expedia
- From $156 per night (USD)
VRBO
Free Parking Luxury Loft Getaway Uptown Montrose Beach WFH Gym Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $156 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Cozy 1-bedroom apartment .luxury building
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This memorable apartment is the perfect home base for your trip to Chicago. Nestled in the heart of the city, this charm ...
From $200 per night (USD)Expedia
- 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 $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
- From $331 per night (USD)
VRBO
Luxurious Avalon Manor
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled in a prime location, this exceptional 4-bedroom, 2 1/2 bath tri-level smart house awaits your arrival. Recently ...
From $331 per night (USD)VRBO
- From $402 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 $402 per night (USD)VRBO
- From $424 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 $424 per night (USD)VRBO
- From $304 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 $304 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 $299 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 $299 per night (USD)VRBO
- From $200 per night (USD)
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. ...
From $200 per night (USD)Expedia
- From $192 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 $192 per night (USD)VRBO
- From $204 per night (USD)
Expedia
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 $204 per night (USD)Expedia
- From $1259 per night (USD)
VRBO
Downtown Penthouse 5bd\/4ba VIEWS, Parking, Gym, Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Welcome to our Two 2-Story Downt ...
From $1259 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)
Expedia
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)Expedia
- 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 $163 per night (USD)
Expedia
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 $163 per night (USD)Expedia
- From $536 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 $536 per night (USD)VRBO
- From $130 per night (USD)
Expedia
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)Expedia
- 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 $270 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 $270 per night (USD)VRBO
- From $305 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 $305 per night (USD)VRBO
- From $96 per night (USD)
Expedia
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 $96 per night (USD)Expedia
- From $180 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 $180 per night (USD)VRBO
- From $352 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 $352 per night (USD)Expedia
- 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 $99 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 $99 per night (USD)Expedia
- From $371 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 $371 per night (USD)VRBO
- From $1202 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 $1202 per night (USD)VRBO
- From $244 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 $244 per night (USD)VRBO
- From $288 per night (USD)
Expedia
2 bedroom Pastel Loft 1 mi from the Chicago Lakefront, close to CTA transit!
- 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 $288 per night (USD)Expedia
- From $135 per night (USD)
VRBO
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 ...
From $135 per night (USD)VRBO
- From $1019 per night (USD)
Expedia
Luxury Loft Collection 903 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $1019 per night (USD)Expedia
- From $988 per night (USD)
VRBO
Luxury Loft Collection 902 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $988 per night (USD)VRBO
- From $149 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 $149 per night (USD)Expedia
- From $130 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 $130 per night (USD)VRBO
- From $146 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 $146 per night (USD)Expedia
- From $120 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 $120 per night (USD)VRBO
- From $122 per night (USD)
Expedia
Chicago Vacation Rental, 19 Mi to Downtown Area!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Explore the vibrant city of Chicago from the comfort of this 4-bedroom, 2-bath vacation rental. Located just minutes awa ...
From $122 per night (USD)Expedia
- From $787 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 $787 per night (USD)VRBO
- From $140 per night (USD)
VRBO
Landing at NEXT - 1 Bedroom in Near North Side
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the NEXT evolution of luxury living. Our apartments come in varied layouts outfitted with contemporary featur ...
From $140 per night (USD)VRBO
- From $1598 per night (USD)
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 ...
From $1598 per night (USD)VRBO
- From $561 per night (USD)
Expedia
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 $561 per night (USD)Expedia
- From $715 per night (USD)
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 ...
From $715 per night (USD)VRBO
- From $1458 per night (USD)
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 ...
From $1458 per night (USD)Expedia
- From $1636 per night (USD)
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 ...
From $1636 per night (USD)VRBO
- From $684 per night (USD)
Expedia
McCormick Place 6 twin beds + Sofa bed 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 • 6 twin size beds + ...
From $684 per night (USD)Expedia
- From $233 per night (USD)
VRBO
South Shore Retreat 5 bedrooms\/entertainment
- Bedrooms:
- 3
- Bathrooms:
- 5
- 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 $233 per night (USD)VRBO
- From $650 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 $650 per night (USD)Expedia
- From $298 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 $298 per night (USD)VRBO
- From $101 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 West Loop furnished one bedroom apartm ...
From $101 per night (USD)Expedia
- From $183 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 West Loop. . It’ll be easy to simply show up and start ...
From $183 per night (USD)VRBO
- From $355 per night (USD)
Expedia
Chicago New 2BR Home w 3 Beds and HighSpeed Internet
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy a stylish experience at this centrally-located home in the eccentric Wicker Park neighborhood of Chicago. ...
From $355 per night (USD)Expedia
- From $180 per night (USD)
VRBO
Bright 3BR\/1BA FREE Parking\/Laundry in Pilsen. Minutes from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Escape to the vibrant heart of Pilsen and experience Chicago like a local in our charming home: -Fully equipped, modern ...
From $180 per night (USD)VRBO
- From $100 per night (USD)
VRBO
Perfect 2BD\/1BA FREE Garage Parking\/Laundry in Pilsen. Minutes to downtown.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover our 2-bed, 1-bath Pilsen gem! Adorned with local art, a workspace, and free parking & laundry, it's minutes fro ...
From $100 per night (USD)VRBO
- From $543 per night (USD)
VRBO
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 $543 per night (USD)VRBO
- From $178 per night (USD)
Expedia
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 $178 per night (USD)Expedia
- From $75 per night (USD)
VRBO
Tranquil 1BR Urban Retreat in Hyde Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to a cozy urban retreat in the heart of Chicago! Our fully furnished 1-bedroom apartment offers a stylish and co ...
From $75 per night (USD)VRBO
- From $153 per night (USD)
Expedia
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 $153 per night (USD)Expedia
- From $800 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 $800 per night (USD)VRBO
- From $188 per night (USD)
VRBO
Modern, Cozy & Chic 2 BR\/1BA Apartment in Lincoln Square\/Ravenswood, Chicago, IL
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our newly renovated apartment in the heart of Lincoln Square! This modern, cozy space features 2 bedrooms w/ ...
From $188 per night (USD)VRBO
- From $378 per night (USD)
VRBO
❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Chicago! Whether you’re in town to seal a business deal or have a short holiday breather, our warm three-bed ...
From $378 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Newly renovated 2 bedroom Garden apartment, Living room, bath,and full kitchen.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Keep it simple at this peaceful and centrally-located place to almost Everything. Newly renovated 3 bedroom apartment, o ...
From $175 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Newly remodeled, 3 bedroom apartment 20 min from almost everything in the city
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Keep it simple at this peaceful and centrally-located place to almost Everything. Newly renovated 3 bedroom apartment, o ...
From $230 per night (USD)VRBO
- From $280 per night (USD)
Expedia
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 $280 per night (USD)Expedia
- From $800 per night (USD)
VRBO
3 Bed Wrigley home w\/view & party deck - 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 $800 per night (USD)VRBO
- From $422 per night (USD)
Expedia
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by RedAwning
- 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 $422 per night (USD)Expedia