Chicago Rentals
From $158 per night (USD)VRBO
Gorgeous Loop 1BR w/ Gym, Pool, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $158 per night (USD)VRBO
From $127 per night (USD)Expedia
Mod West Loop 1BR w/ Pool, Gym, nr. Fulton Market & L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop with views over the city. It’ll be easy to si ...
From $127 per night (USD)Expedia
From $269 per night (USD)VRBO
Generous River North 3BR w/ Gym, Rooftop, walk to L & Park, by Blueground (ID #CHI324)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the best of Chicago, with this three bedroom apartment in River North with balcony views over the city. It’ll b ...
From $269 per night (USD)VRBO
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Rad West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop with views over the city. It’ll be easy to si ...
Click For PricingExpedia
From $454 per night (USD)VRBO
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful, modern and newly furnished 4br/2 bath condo at a desirable location for business conventions and vacation tra ...
From $454 per night (USD)VRBO
From $249 per night (USD)Expedia
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Beautiful, newly renovated condo located in the heart of Chicago Chinatown with 2 bedroom, 1 bath, a spacious living roo ...
From $249 per night (USD)Expedia
From $458 per night (USD)VRBO
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Newly remodeled apartment with 4 bedrooms, 4 bathrooms, a spacious & modern living area, FREE private parking and plenty ...
From $458 per night (USD)VRBO
From $447 per night (USD)Expedia
4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 11
Beautiful, modern and newly furnished 4 br/1.5 bath condo at a desirable location for both business conventions and vaca ...
From $447 per night (USD)Expedia
From $224 per night (USD)VRBO
Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Charming Oasis! Step into this delightful 3-BR, 1-BA retreat in a friendly neighborhood with views of a ...
From $224 per night (USD)VRBO
From $224 per night (USD)VRBO
Spacious 2-BR Condo + Free On-Site Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $224 per night (USD)VRBO
From $1187 per night (USD)VRBO
Downtown Sleep 20 | Mag Mile 6bd/6ba
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐚𝐭 𝐨𝐮𝐫 𝐪𝐮 ...
From $1187 per night (USD)VRBO
From $313 per night (USD)VRBO
Best Lincoln Square Location - Spacious 2 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming apartment in an updated 1800s beautiful brick building. Located in the heart of Chicago's Lincoln Square neighb ...
From $313 per night (USD)VRBO
From $215 per night (USD)VRBO
Amazing Lakeview 1BR w/ Rooftop Pool, near Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Lake View East furnished one bedroom a ...
From $215 per night (USD)VRBO
From $156 per night (USD)Expedia
Stunning Lakeview 1BR w/ Rooftop Pool, near Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Lake View East furnished one be ...
From $156 per night (USD)Expedia
From $639 per night (USD)VRBO
Adorable single family home in Logan Square
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
I bought this house in Spring of 2016 and have been remodeling and updating it. There are 2 bedrooms upstairs with a ful ...
From $639 per night (USD)VRBO
From $276 per night (USD)Expedia
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and club ...
From $276 per night (USD)Expedia
From $642 per night (USD)VRBO
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Wrigleyville condo is located 1/2 block from Wrigley Field and Clark Street. Also close to Southport corridor and Brown ...
From $642 per night (USD)VRBO
From $220 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 $220 per night (USD)Expedia
From $1264 per night (USD)VRBO
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 20
Luxurious Upscale Duplex Penthouse Property - Sleeps up to 14 people with over 5600 sq ft in this Duplex Penthouse! Rec ...
From $1264 per night (USD)VRBO
From $256 per night (USD)Expedia
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nicely renovated, modern kitchen and bath, comfortable beds, and solar-powered. Great location in a safe neighborhood, J ...
From $256 per night (USD)Expedia
From $614 per night (USD)VRBO
Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
This is THE place to stay for all things Chicago. Everything you need is here: * Fabulous well stocked chef's kitch ...
From $614 per night (USD)VRBO
From $242 per night (USD)Expedia
Cozy 2BR haus inn Pilsen with patio and fire pit 🔥
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Forget your worries in this spacious and serene space. You have many options steps away including a byob pizza parlor, t ...
From $242 per night (USD)Expedia
From $148 per night (USD)VRBO
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Licensed by the City of Chicago: Studio 1: 2209375 Immaculately clean, quiet studio, housed in a brick coach house off ...
From $148 per night (USD)VRBO
From $383 per night (USD)Expedia
3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
New condo in the heart of Chicago Chinatown with 3 bedrooms, 2 baths, a spacious living area and FREE private parking. T ...
From $383 per night (USD)Expedia
From $296 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 $296 per night (USD)VRBO
From $225 per night (USD)Expedia
Family-friendly, stylish Chicago Apartment in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Hamlin House! The living area has beautifully restored hardwood floors and the bathroom was completely renova ...
From $225 per night (USD)Expedia
From $285 per night (USD)VRBO
3 BD condo near to downtown, Gold Coast and Michigan Avenue.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Situated on quiet side street across from 19c. church, steps from popular bars, restaurants, and public transportation. ...
From $285 per night (USD)VRBO
From $828 per night (USD)Expedia
Luxéry Stay \"Hollywood\" Downtown/McCormick/WinTrust Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Experience the best of Chicago from this stunning 3-bedroom apartment in the South Loop. With its elegant desig ...
From $828 per night (USD)Expedia
From $212 per night (USD)VRBO
50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Step into the vibrant heart of River North, where your window frames forever views and the sky blushes with the best s ...
From $212 per night (USD)VRBO
From $354 per night (USD)Expedia
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
You will be transported when you stay with us in this hip and charming space in Chicago's most vibrant neighborhood! Enj ...
From $354 per night (USD)Expedia
From $463 per night (USD)VRBO
DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $463 per night (USD)VRBO
From $486 per night (USD)Expedia
Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $486 per night (USD)Expedia
Click For PricingVRBO
Luxe Ranch & Spa House Retreat! Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
We now have the newly renovated Hot Tub Room off the rear yard with additional indoor tiled bench style seating. The ho ...
Click For PricingVRBO
From $200 per night (USD)Expedia
Trendy Streeterville Studio w/ Pool & Gym, nr Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $200 per night (USD)Expedia
From $211 per night (USD)VRBO
Lovely 3-bedroom apartment in Bronzeville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our spacious 3-bedroom, 2-bathroom apartment on the 3rd floor of a multi-unit walk-up. Enjoy the convenience ...
From $211 per night (USD)VRBO
From $224 per night (USD)Expedia
Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 4
Book your Holiday-Get-away! This luxury space is elegantly adorned with central air, ample room for living, entertaining ...
From $224 per night (USD)Expedia
From $77 per night (USD)VRBO
Sleek Edgewater 1BR w/ Gym, Deck & Lounge, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Edgewater Beach furnished one bedroo ...
From $77 per night (USD)VRBO
From $139 per night (USD)Expedia
lovely and cozy vintage two bedroom, 🐾friendly apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Comfy and cozy, second floor apartment located in an incredibly beautiful & safe neighborhood on chicago’s northwest sid ...
From $139 per night (USD)Expedia
From $89 per night (USD)VRBO
Modern Gold Coast 1BR w/ Doorman & Gym, 2 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $89 per night (USD)VRBO
From $167 per night (USD)VRBO
Ukrainian Village Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the heart of Ukrainian village and just a few short minutes from downtown, your family will be close to every ...
From $167 per night (USD)VRBO
From $684 per night (USD)VRBO
As Seen on TV: Safest Area Lincoln Park Duplex
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
** As featured on upcoming Season 3 of CBS' TV show "Staycation". ** Come stay in a tasteful DUPLEX in the heart of Ch ...
From $684 per night (USD)VRBO
From $295 per night (USD)Expedia
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy your stay in this 3-BR/2-bath vintage duplex unit located on a serene, residential side street walking distance to ...
From $295 per night (USD)Expedia
From $255 per night (USD)VRBO
*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations s ...
From $255 per night (USD)VRBO
From $294 per night (USD)VRBO
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations s ...
From $294 per night (USD)VRBO
From $243 per night (USD)VRBO
Sew u wana stay in a storefront?
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
If you're staying in Chicago and want to experience Wicker Park, you gotta stay in a space as unique as the neighborhood ...
From $243 per night (USD)VRBO
From $195 per night (USD)Expedia
Bridgeport Boho Chic Vibes
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your new home away from home in this 2 bedroom apartment in the classic Chicago neighborhood of Bridgeport, t ...
From $195 per night (USD)Expedia
From $197 per night (USD)VRBO
Entire Below Level Studio w/ Private Sauna
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Centrally located between Logan Sq., Bucktown, Wicker Park & Ukrainian Village. Easily jump on the 606 walk/bike path or ...
From $197 per night (USD)VRBO
Click For PricingExpedia
4BD Condo w/Parking & Game Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our luxurious 4-bedroom, 2.5-bathroom condo unit that's perfect for your stay in Chicago. This stunning unit ...
Click For PricingExpedia
From $228 per night (USD)VRBO
Large Group Home
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 16
Great accommodations for up to 16 people great for family gatherings and team accommodations it is a very clean and quie ...
From $228 per night (USD)VRBO
From $484 per night (USD)Expedia
Spacious 2BR in The Loop + 5-Star Comfort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: 'The Cooke' is your ideal base for exploring Chicago's vibrant attractions, promising a luxurious stay with uni ...
From $484 per night (USD)Expedia
Click For PricingVRBO
Amazing Edgewater 2BR, nr Lake Michigan, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Edgewater Beach furnished two bedroom ...
Click For PricingVRBO
From $214 per night (USD)Expedia
Luxury Villa 10 minutes to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Windy City! La Villita is the gateway to Chicago's vibrant Mexican-American area. Super cozy , modern and ...
From $214 per night (USD)Expedia
From $794 per night (USD)VRBO
Eddy House, Roscoe Village Haven
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Steps away from Roscoe Village dining & shopping and a short train to the Mag Mile. Enjoy the best Chicago has to offer ...
From $794 per night (USD)VRBO
From $202 per night (USD)Expedia
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This newly updated 2 bedroom, 1 bath condo has everything you need to make your Chicago stay perfect! The home was thou ...
From $202 per night (USD)Expedia
From $829 per night (USD)VRBO
Wrigley 2 bedroom 2 bath with free parking & yard!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: My home is a very large 2 bedroom 2 bath condo 3 blocks (6 minute stroll) from Wrigley Field. It's 20 minutes ...
From $829 per night (USD)VRBO
From $408 per night (USD)Expedia
Penthouse Escape + Vibrant West Loop Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Discover 'The Fitz,' a designer 3BR penthouse ideal for your Chicago getaway, with top marks for cleanliness an ...
From $408 per night (USD)Expedia
From $570 per night (USD)VRBO
Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 20
Lots of room for you to stretch out and enjoy the great location in East Lakeview. Nearby to public transportation incl ...
From $570 per night (USD)VRBO
From $357 per night (USD)Expedia
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to MAYORS MANOR, with a 24/7 dedicated team ensuring a comfortable and unforgettable stay. ✔ Spacious & Stylish ...
From $357 per night (USD)Expedia
From $306 per night (USD)VRBO
McCormick Place city view 2br/2ba with optional parking/sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $306 per night (USD)VRBO
From $218 per night (USD)Expedia
Quiet Area - Revamped Basement
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your cozy retreat! Our 2-bedroom short-term rental is designed to offer you a comfortable and convenient stay ...
From $218 per night (USD)Expedia
From $240 per night (USD)VRBO
Elegant 3 Bedroom and 1 Bath Apartment
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Experience top quality in a spacious 3 bed 1 bath apartment during your next visit to Chicago. We are located in West Ri ...
From $240 per night (USD)VRBO
From $410 per night (USD)VRBO
STYLISH-LOCAL-COMFY-SAFE 5 night min.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Conveniently located in Chicago to all of Chicago. Located in Chicago’s Andersonville & Edgewater area. Down the stre ...
From $410 per night (USD)VRBO
From $254 per night (USD)VRBO
Modern luxury apartment in West Town Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Looking for a luxurious getaway in the heart of the city? Look no further than this stunning 3 bedroom, 2 bath modern ap ...
From $254 per night (USD)VRBO
From $211 per night (USD)Expedia
Beautiful 1st floor apartment.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
We have the spot you would love. Perfect for a cozy get away. Our unit is central to the city and has easy access to do ...
From $211 per night (USD)Expedia
From $379 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 $379 per night (USD)VRBO
From $211 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 $211 per night (USD)VRBO
From $552 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 $552 per night (USD)VRBO
From $449 per night (USD)Expedia
Fremont St. Guesthouse - Unit 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Classic Chicago Brownstone, updated 3 bedroom and 2 bathroom high end, 1st floor condo. Located on beautiful Fremont Str ...
From $449 per night (USD)Expedia
From $423 per night (USD)VRBO
Beautiful Downtown 3BR with Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
A beautiful and modern three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'l ...
From $423 per night (USD)VRBO
From $267 per night (USD)Expedia
The Neighborhood Hotel - Little Italy Two Bedroom - ADA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 ADA BATHROOM This airy, two bedroom suite exudes a mid-century Ital ...
From $267 per night (USD)Expedia
From $268 per night (USD)VRBO
The Neighborhood Hotel - Little Italy One Bedroom w/ Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 KING BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM + PATIO This airy, one bedroom suite exudes a mid-century Italian meets ...
From $268 per night (USD)VRBO
From $434 per night (USD)VRBO
Chic River North Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to our Chic River North Retreat, a hidden gem in vibrant River North, Chicago. Discover a rare 2-bedroo ...
From $434 per night (USD)VRBO
From $236 per night (USD)VRBO
Beautiful Chicago 2BD 1BA, minutes from Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect Humboldt Park location! 2 minute walk to CTA bus on Grand Ave , North Ave, or Pulaski. Minutes from 606 Trail. T ...
From $236 per night (USD)VRBO
From $264 per night (USD)VRBO
Ultimate City Life Experience in Heart of Chicago | 2 Family Ready Roos
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $264 per night (USD)VRBO
From $138 per night (USD)VRBO
Cozy Corner in Chicago’s Downtown| Walking Distance to Ohio Street Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 1200 sq. ft, equipped with complimentary toiletries, TV, avai ...
From $138 per night (USD)VRBO
From $426 per night (USD)VRBO
Loft8 - Unique Design in Prime Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Layout --- 1,500 sq ft, 3 king size beds, 2 full bathrooms, 1 separate room with desk next to patio (great natural light ...
From $426 per night (USD)VRBO
From $289 per night (USD)VRBO
The Norwood Nook – Walkable Stay Near O’Hare & Metra!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
- Upper unit within two-unit building - 5 miles to O’Hare Airport - 10 minute drive without traffic - Blackout curtains ...
From $289 per night (USD)VRBO
From $128 per night (USD)VRBO
Walk to Train & Bus: Updated Chicago Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
5 Mi to Midway | Close to Hospitals | On Main Road in Residential Area Your extended stay in Chicago is made easy at th ...
From $128 per night (USD)VRBO
From $527 per night (USD)VRBO
Splendid Corner 3BR in the Loop | City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $527 per night (USD)VRBO
From $1301 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 $1301 per night (USD)Expedia
From $378 per night (USD)VRBO
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 $378 per night (USD)VRBO
From $140 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 $140 per night (USD)Expedia
From $153 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 $153 per night (USD)VRBO
From $470 per night (USD)Expedia
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 $470 per night (USD)Expedia
From $352 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 $352 per night (USD)VRBO
From $175 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 $175 per night (USD)Expedia
From $158 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 $158 per night (USD)VRBO
From $1002 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 $1002 per night (USD)VRBO
From $298 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 $298 per night (USD)VRBO
From $215 per night (USD)Expedia
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 $215 per night (USD)Expedia
From $633 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 $633 per night (USD)VRBO
From $315 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 $315 per night (USD)Expedia
From $582 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 $582 per night (USD)VRBO
From $391 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 $391 per night (USD)Expedia
From $88 per night (USD)VRBO
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 $88 per night (USD)VRBO
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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
Click For PricingVRBO
Newly-renovated historic home in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Bright, comfy, and stylish space just steps from all that Logan Square has to offer! You'll have the whole place to your ...
Click For PricingVRBO
From $128 per night (USD)VRBO
Historic Chicago Bungalow – on NW Side
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Traditional 1912 Chicago bungalow on an oversized lot with antiques plus all the modern amenities you would expect: cent ...
From $128 per night (USD)VRBO
From $103 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 $103 per night (USD)VRBO
From $399 per night (USD)Expedia
Wrigley Penthouse w/Private Roof Deck and Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stunning 3BR, 2.5BA penthouse with chef's kitchen, Viking appliances, private rooftop deck, Weber grill, smoker, master ...
From $399 per night (USD)Expedia