Chicago Rentals
From $881 per night (USD)VRBO
Ultra-modern 4BR/2.5BA Uptown/Edgewater duplex, featuring a rooftop deck with fire pit and easy access to the lake, dining, shopping, and Chicago’s cultural highlights.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
🌟 New 4BR Duplex in Uptown/Edgewater! 🌟 This ultra-modern 2500+ SF duplex is steps from Lake Michigan, Andersonville, ...
From $881 per night (USD)VRBO
From $286 per night (USD)VRBO
Game Day Getaway - 3BR in Vibrant Wrigleyville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
An excellent location in the vibrant heart of Wrigleyville! It's a brief 5-minute stroll to Wrigley Field and just aroun ...
From $286 per night (USD)VRBO
From $596 per night (USD)VRBO
Modern 6BR House Steps to Wrigleyville
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
Fantastic location in the heart of Wrigleyville! Just a 5-minute walk to Wrigley Field and a block from The Metro concer ...
From $596 per night (USD)VRBO
From $183 per night (USD)VRBO
Cozy Logan Square Studio, Wi-Fi & AC, Quick Downtown Access
- Bedrooms:
- 0
- Bathrooms:
- 1
- Sleeps:
- 2
Ideally situated in the vibrant heart of Logan Square, this home places you just steps from acclaimed restaurants, cozy ...
From $183 per night (USD)VRBO
From $239 per night (USD)VRBO
Updated 3 Bedroom Chicago Downtown Pilsen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Experience Chicago and Pilsen as being in the heart of 18th st. Some of the best food, music and nightlife Chi ...
From $239 per night (USD)VRBO
From $206 per night (USD)VRBO
Charming 3-bedroom smart house in fabulous Chicago with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in Chicago, this delightful smart house offers 3 cozy bedrooms - 2 with queen beds and 1 with a sofa bed. The ba ...
From $206 per night (USD)VRBO
From $343 per night (USD)VRBO
South Loop 3BD 2BA Condo with Balcony and Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Discover this modern 3-bedroom condo on Michigan Avenue, ideally situated in the South Loop, one of Chicago’s ...
From $343 per night (USD)VRBO
From $401 per night (USD)VRBO
Chic Chinatown Apt w parking!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1 ...
From $401 per night (USD)VRBO
From $3285 per night (USD)VRBO
Iconic Downtown Penthouses Getaway + City Views
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 15
Summary: 'The Lyra' pairs two exquisite penthouses for a unique Chicago experience perfect for groups seeking both leis ...
From $3285 per night (USD)VRBO
From $115 per night (USD)VRBO
Modern and Stylish Private1BR Garden Apt in Logan Square With Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our cozy and modern West Logan Square garden apartment in one of Chicago's up-and-coming neighborhoods! The ...
From $115 per night (USD)VRBO
From $418 per night (USD)VRBO
Spacious 5-bedroom bungalow in delightful Chicago with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Make yourself at home in this 5-bedroom Chicago retreat. This adorable bungalow features 2 queen beds, 2 twin beds, and ...
From $418 per night (USD)VRBO
From $1572 per night (USD)VRBO
Ideal for Groups: Spacious 2BR in The Loop
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Discover 'The Poppy,' your group's vibrant home base in The Loop, offering two stylish apartments with breatht ...
From $1572 per night (USD)VRBO
From $798 per night (USD)VRBO
Premium 2BR Apartments in Lincoln Park
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: For families and large groups, 'The Ash' makes your Chicago stay easy, offering two spacious apartments with W ...
From $798 per night (USD)VRBO
From $255 per night (USD)Expedia
Charming 2-bedroom 1 bathroom Bridgeport Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This Chicago unit 2 inviting bedrooms with 1 full bed and 1 bunk bed in Bridgeport . The cozy space includes heating, an ...
From $255 per night (USD)Expedia
From $494 per night (USD)VRBO
Chic 2-bedroom apartment in vibrant Chicago with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of Chicago from this 2-bedroom apartment. This delightful space features 1 bunk bed and 1 full bed, ...
From $494 per night (USD)VRBO
From $798 per night (USD)VRBO
Luxury Designer Penthouse Combo |North| Gold Coast
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthous ...
From $798 per night (USD)VRBO
From $798 per night (USD)VRBO
Luxury Designer Penthouse Combo |South| Gold Coast
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthous ...
From $798 per night (USD)VRBO
From $594 per night (USD)Expedia
Luxury Loft Collection 901 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious ...
From $594 per night (USD)Expedia
Click For PricingVRBO
United Center Compound w/Rooftop, Hot Tub, Sauna
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 18
Summary: Welcome to the Chicago Mid-Century Gem, an extraordinary urban retreat. With easy access to the CTA Green Lin ...
Click For PricingVRBO
From $291 per night (USD)Expedia
Medical District 2BR with Jacuzzi & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Spacious 2-bed, 2-bath Chicago retreat in the Illinois Medical District, perfect for 4 guests. Enjoy a jetted tub, dedic ...
From $291 per night (USD)Expedia
From $471 per night (USD)VRBO
Luxury Designer Penthouse 3804 | Pool | Gold Coast
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's cente ...
From $471 per night (USD)VRBO
From $802 per night (USD)VRBO
Family, Groups - Convenient to Wrigley, Loop, Airport - Spacious 2200 Sq Ft
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking a ...
From $802 per night (USD)VRBO
From $187 per night (USD)VRBO
2BD/1 BA with summer patio in quiet Roscoe Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/ ...
From $187 per night (USD)VRBO
From $289 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 $289 per night (USD)VRBO
From $222 per night (USD)VRBO
2F - ❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
<p>Welcome to Chicago!</p> <p> </p> <p>Whether you’re in town to seal a business deal or have a short holiday breather ...
From $222 per night (USD)VRBO
From $193 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 $193 per night (USD)VRBO
From $323 per night (USD)VRBO
River North 2BD Condo: Parking, Balcony, Laundry
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to our riverfront oasis in Chicago's vibrant River North neighborhood! Start your morning with a strol ...
From $323 per night (USD)VRBO
From $423 per night (USD)Expedia
Warm & Spacious 4BR Home Long Stays Welcome
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your cozy Chicago home away from home — a spacious 4-bedroom, 3-bath retreat perfect for families, business t ...
From $423 per night (USD)Expedia
From $249 per night (USD)VRBO
River North 2BD 2BA Retreat with Balcony & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Wake up in the heart of River North, where Chicago's best restaurants, rooftop bars, boutiques, and art galler ...
From $249 per night (USD)VRBO
From $251 per night (USD)Expedia
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 $251 per night (USD)Expedia
From $432 per night (USD)VRBO
Unique Chicago Penthouse Loft - Amazing Deal & Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ideal for a Chicago getaway, a business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (n ...
From $432 per night (USD)VRBO
From $279 per night (USD)VRBO
Chic Ukrainian Village Home: 4 Bedrooms 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our Chic 4-Bedroom Haven in Ukrainian Village, Chicago! Explore nearby Wicker Park, West Town, the ...
From $279 per night (USD)VRBO
From $263 per night (USD)VRBO
Foosball, Steps from Wrigley, Private Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Enjoy this beautiful space, just minutes away from the very best Chicago has to offer! This condo is walking d ...
From $263 per night (USD)VRBO
From $235 per night (USD)VRBO
Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our spacious and stylish 3-bedroom, 3-bath condo located in the vibrant, historic Bronzeville community of Ch ...
From $235 per night (USD)VRBO
From $882 per night (USD)VRBO
The Grand Kimball Lodge, Logan Square, Sleeps 15
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
The Grand Kimball Lodge is a premier Logan Square loft and a trusted production site for brands like Adidas, Ford, Jack ...
From $882 per night (USD)VRBO
From $121 per night (USD)VRBO
Stunning Suite 2 @ Hotel Nemo Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Hotel Nemo is a boutique, corporate guest house stylishly designed for those who want to stay just around the c ...
From $121 per night (USD)VRBO
From $296 per night (USD)VRBO
The Norwood Nook – Walkable Stay Near O’Hare & Metra!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
-5 miles to O’Hare Airport 10 minutes drive without traffic -2nd Floor Apartment within a two-unit building** You will ...
From $296 per night (USD)VRBO
From $152 per night (USD)VRBO
Sunny Lakeview 1BR w/ Rooftop & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $152 per night (USD)VRBO
From $228 per night (USD)VRBO
Open Lakeview 2BR w/ Gym & Grills, nr Lakefront Trail, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Lake View East with balcony views over the city. It’ll ...
From $228 per night (USD)VRBO
From $114 per night (USD)VRBO
Dreamy Streeterville Studio w/ Pool & Gym, nr Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the city. It’l ...
From $114 per night (USD)VRBO
From $337 per night (USD)VRBO
2-Car Parking, PingPong, Arcade, 3 Floors!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: As soon as you step inside, you'll be struck by the open floor plan and sleek design. The living room is the p ...
From $337 per night (USD)VRBO
From $146 per night (USD)Expedia
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 $146 per night (USD)Expedia
From $400 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 $400 per night (USD)VRBO
From $242 per night (USD)Expedia
The Neighborhood Hotel - Little Italy One Bedroom - ADA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 KING BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM ADA This airy, one bedroom suite exudes a mid-century Italian meets slee ...
From $242 per night (USD)Expedia
From $247 per night (USD)VRBO
The Neighborhood Hotel - Little Italy LI
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
1 KING BED + 1 BATHROOM This airy studio exudes a mid-century Italian meets sleek urban loft vibe. Pops of color compli ...
From $247 per night (USD)VRBO
From $328 per night (USD)Expedia
The Neighborhood Hotel - Little Italy Two Bedroom w/ Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM + BALCONY This airy, two bedroom suite exudes a mid-centur ...
From $328 per night (USD)Expedia
From $281 per night (USD)VRBO
The Neighborhood Hotel - Little Italy Two Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM This airy, two bedroom suite exudes a mid-century Italian ...
From $281 per night (USD)VRBO
From $265 per night (USD)Expedia
The Neighborhood Hotel - Little Italy One Bedroom w/ Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 KING BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM + BALCONY This airy, one bedroom suite exudes a mid-century Italian meet ...
From $265 per night (USD)Expedia
From $281 per night (USD)VRBO
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 $281 per night (USD)VRBO
From $272 per night (USD)Expedia
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 $272 per night (USD)Expedia
From $509 per night (USD)VRBO
STYLISH-LOCAL-COMFY-SAFE 4 night min.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Chicago’s Andersonville & Edgewater area. Down the street from Loyola's campus and near great restaurants ...
From $509 per night (USD)VRBO
From $354 per night (USD)Expedia
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 $354 per night (USD)Expedia
From $1354 per night (USD)VRBO
DTown Penthouse - 4bd/4ba (+Parking + Gym )
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Feel at Home, Unwind, and Enjoy the amenities you deserve with two 2-Story Downtown Penthouses with Million $ Views. Gu ...
From $1354 per night (USD)VRBO
From $202 per night (USD)Expedia
50th Floor Mag Mile Views, Balcony, Pool, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Soar 50 stories above downtown Chicago in this modern Studio apartment with breathtaking city views. Perfect f ...
From $202 per night (USD)Expedia
From $415 per night (USD)VRBO
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 $415 per night (USD)VRBO
From $501 per night (USD)Expedia
DTown Penthouse 2bd +Parking, Gym, Pvt Patio
- 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 $501 per night (USD)Expedia
From $674 per night (USD)VRBO
Dtown Penthouse 11+Parking, Gym, Pvt Patio
- 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 $674 per night (USD)VRBO
From $118 per night (USD)VRBO
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 $118 per night (USD)VRBO
From $404 per night (USD)VRBO
Modern 3BR & 2BA Near McCormick & Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the perfect home base for your next Chicago visit. Located on the 3rd floor of a classic multi-unit building on ...
From $404 per night (USD)VRBO
From $256 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 $256 per night (USD)Expedia
From $136 per night (USD)VRBO
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 $136 per night (USD)VRBO
From $194 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 $194 per night (USD)VRBO
From $1301 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 $1301 per night (USD)VRBO
From $492 per night (USD)VRBO
Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
House located in Lakeview / Lincoln Park - close to other popular Chicago neighborhoods. New furniture throughout house. ...
From $492 per night (USD)VRBO
From $228 per night (USD)VRBO
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 $228 per night (USD)VRBO
From $836 per night (USD)Expedia
4BR Old Town Chicago Loft | Walk to Wells St
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
If you’re coming to Chicago and want space, comfort, and a location that truly works—you’ve found it. This is not a typ ...
From $836 per night (USD)Expedia
From $187 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 $187 per night (USD)VRBO
From $603 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 $603 per night (USD)VRBO
From $460 per night (USD)VRBO
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 $460 per night (USD)VRBO
From $417 per night (USD)Expedia
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 $417 per night (USD)Expedia
From $458 per night (USD)VRBO
W3 - Spacious 2BR Apt + 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 $458 per night (USD)VRBO
From $445 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 $445 per night (USD)VRBO
From $601 per night (USD)VRBO
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This single family home w/garage is in desirable LOGAN SQUARE - our 5 bedroom / 4 bath is a 15 minute drive away from Do ...
From $601 per night (USD)VRBO
From $588 per night (USD)Expedia
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 (first-com ...
From $588 per night (USD)Expedia
From $594 per night (USD)VRBO
4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful, modern and newly furnished 4 br/1.5 bath condo at a desirable location for both business conventions and vaca ...
From $594 per night (USD)VRBO
From $130 per night (USD)VRBO
Hip River North 1BR w/ Gym + Pool + W/D near Mag Mile 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 $130 per night (USD)VRBO
From $267 per night (USD)VRBO
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this cozy, calm and stylish 1 bedroom, 1 bath unit with a spacious kitchen, a dedicated work spac ...
From $267 per night (USD)VRBO
From $193 per night (USD)Expedia
❤️ Modern 2BR Apt Right next to Wrigley Field & Transit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience city life; Located in Wrigley! Feel like a local! ✔️Right Next to Wrigley Field (1 block away); Home of Chi ...
From $193 per night (USD)Expedia
From $864 per night (USD)VRBO
River North 3BR/2BA: HUGE, Parking, Center Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Experience an urban oasis unlike any other: - Complimentary parking for one vehicle in our attached lot - Spacious, re ...
From $864 per night (USD)VRBO
From $645 per night (USD)VRBO
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: [NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Winter/Spring 2027. The ...
From $645 per night (USD)VRBO
From $148 per night (USD)VRBO
Lg Studio Apt. No cleaning fee. Obama Center 10 mins.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Beautiful, comfortable, PRIVATE garden unit of a 3 floor home located in the historic Bronzeville neighborhood of Chicag ...
From $148 per night (USD)VRBO
From $602 per night (USD)Expedia
Luxury Modern home minutes from Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Newly rehabbed single family home with parking in Chicago's popular Pilsen neighborhood. Close to transportation, 18th s ...
From $602 per night (USD)Expedia
From $109 per night (USD)VRBO
Smart Loop 1BR w/ Pool, Gym, nr. Financial District, 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 $109 per night (USD)VRBO
From $137 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 The Loop with views over the city. It’ll be easy to sim ...
From $137 per night (USD)VRBO
From $121 per night (USD)VRBO
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 $121 per night (USD)VRBO
From $131 per night (USD)VRBO
Roomy Lakeview 1BR w/ W/D, Gym, near Lakefront Trail, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $131 per night (USD)VRBO
From $113 per night (USD)VRBO
Generous River North 1BR w/ Gym, Rooftop walk to L and Parks, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...
From $113 per night (USD)VRBO
From $114 per night (USD)VRBO
Hip Loop 1BR w/ Gym, Pool, W/D, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy The Loop furnished one bedroom apartment ...
From $114 per night (USD)VRBO
From $113 per night (USD)VRBO
Smart Loop 1BR w/ Gym, Pool, near Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $113 per night (USD)VRBO
From $621 per night (USD)Expedia
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 $621 per night (USD)Expedia
From $320 per night (USD)VRBO
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 $320 per night (USD)VRBO
From $307 per night (USD)VRBO
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot top-floor corner penthouse with oversize windows, an open layout, and dramatic city ...
From $307 per night (USD)VRBO
From $104 per night (USD)VRBO
Luxe West Loop 1BR w/ Gym, Pool, Coworking, walk to UIC, 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 $104 per night (USD)VRBO
From $534 per night (USD)Expedia
LakeHouse with rooftop and views of lake.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Beautifully renovated luxury residence featuring 3 spacious suites, designer furnishings, antique Murano and Luminaire c ...
From $534 per night (USD)Expedia
From $774 per night (USD)VRBO
Wrigley Field/Lakeview -Entire Home- Large Groups!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 20
"Welcome to your exclusive 2-story haven flooded with natural light! Dual TV areas with brand new 70" and 55" TVs create ...
From $774 per night (USD)VRBO
From $105 per night (USD)VRBO
Luxe West Loop Studio w/ Gym, Pool, Coworking, walk to UIC, 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 $105 per night (USD)VRBO
From $205 per night (USD)VRBO
Comfortable and Trendy Design 1BR in Lincoln Square
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Requires walking up 2 flights of stairs. Old building that has radiant heat controlled by building management. Located ...
From $205 per night (USD)VRBO
From $388 per night (USD)VRBO
Bucktown Home - Rooftop Deck, Game Rm, & Garage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Welcome to our wonderful home in Chicago! This spacious Bucktown retreat is designed for unforgettable group ...
From $388 per night (USD)VRBO
From $341 per night (USD)VRBO
2R- ❤️ Stylish and Cozy 2BR in Logan Square!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Welcome to Chicago! Our large 2-bedroom / 1 bathroom apartment unit is perfect for getaway to Chicago. Stretch out on ...
From $341 per night (USD)VRBO
From $269 per night (USD)Expedia
3BR Spacious Home Away From Home. Coziest neighborhood in Chicago.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Windy City and home of amazing restaurants, great sports teams, and of course the lake! Whether you are t ...
From $269 per night (USD)Expedia