Chicago Rentals
From $399 per night (USD)VRBO
Beautiful 2-bedroom apartment near united center/few minutes to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this charming apartment in Chicago. With two cozy bedrooms featuring 3 queen beds, guests can enjoy a restful ...
From $399 per night (USD)VRBO
From $435 per night (USD)VRBO
Spacious 5-bedroomDuplex in lovely South Shore with AC
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 10
Spacious 5-Bedroom, 2-Bath Updated Duplex in South Shore | Chicago Looking for a comfortable Chicago stay with plent ...
From $435 per night (USD)VRBO
From $115 per night (USD)VRBO
Western Logan Square near Healy Metra Stop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Please contact me with your reservation dates of less than 31 night. T ...
From $115 per night (USD)VRBO
From $490 per night (USD)VRBO
Spacious 7-bedroom house in Chicago with 2 Car Garage/parking Pod/Mins to DT
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 14
Discover the beauty of Chicago from this 7-bedroom house. Each room features a comfortable queen bed, perfect for a rest ...
From $490 per night (USD)VRBO
From $302 per night (USD)VRBO
2 BR Apt. — Near U Chicago Campus + the Lakefront !
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your Chicago adventure begins at this 2-bedroom apartment. Inside, guests find two comfortable queen beds and a beautifu ...
From $302 per night (USD)VRBO
From $315 per night (USD)VRBO
A 3-bedroom, 2-bathroom residence that provides ample space and comfort.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your Chicago adventure begins at this 3-bedroom apartment. Step into a nice and serene space where guests can relax afte ...
From $315 per night (USD)VRBO
From $182 per night (USD)VRBO
The Huron Loft | Near Magnificent Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Stay in the heart of Chicago at The Huron Loft, perfectly located near the Magnificent Mile, Michigan Avenue, ...
From $182 per night (USD)VRBO
From $322 per night (USD)VRBO
Stunning Corner 2BR in the Loop | City & Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city a ...
From $322 per night (USD)VRBO
From $257 per night (USD)VRBO
Rooftop Reverie | Prime Location - Modern-Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern 3BR/2BA condo in the heart of vibrant Pilsen, a prime and centrally located neighborhood with quick access to dow ...
From $257 per night (USD)VRBO
From $246 per night (USD)VRBO
Cozy Chicago Smoke Ok 3BR Suite Near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your urban escape in Chicago’s vibrant South Loop neighborhood! This stunning 3-bedroom, 2-bathroom apartment ...
From $246 per night (USD)VRBO
From $132 per night (USD)VRBO
Comfy 3Bdrm near LSD,Obama Center, UIC, Sci Museum
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
South Shore located along Chicago’s shoreline, with stunning views of Lake Michigan. This location is a perfect stay. G ...
From $132 per night (USD)VRBO
From $561 per night (USD)VRBO
Gold Coast, Downtown Chicago, Sleeps 20
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 20
Summary: Gold Coast Jumbo Duplex-Down LOCATION! LOCATION! LOCATION! DOWNTOWN CHICAGO! The perfect crash pad, w ...
From $561 per night (USD)VRBO
From $308 per night (USD)VRBO
River West 4BD Home: Perfect for Families & Groups
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our stunning 4-bedroom retreat in Chicago's River West neighborhood. Walk to local cafés and brewer ...
From $308 per night (USD)VRBO
From $218 per night (USD)VRBO
Pilsen 2BA Condo Minutes from Chicago Attractions
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Experience Chicago like a local from this beautifully renovated retreat in the heart of Pilsen. Wake up in a s ...
From $218 per night (USD)VRBO
From $259 per night (USD)VRBO
Serene Avondale Triangle Apartment I Near Wrigley/Transit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Savor the privacy, comfort, and location in this Avondale apartment. Steps to the Belmont Blue Line train from O'Hare an ...
From $259 per night (USD)VRBO
From $424 per night (USD)VRBO
Wicker Park 4BD Home: Parking, Theater, & Rooftop
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Summary: Elevate your Chicago getaway in this luxurious Wicker Park retreat. Cook in a chef's kitchen, unwind in your p ...
From $424 per night (USD)VRBO
From $347 per night (USD)VRBO
Amazing Penthouse: Views, Hot Tub, Cold Plunge!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: Experience city living in this stylish 3BD/3BA duplex penthouse in the heart of Wicker Park! Just a 2-minute w ...
From $347 per night (USD)VRBO
From $544 per night (USD)VRBO
Designer Oasis - Sauna, Hot Tub, Patios, Game room
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: Experience Chicago in style from this one-of-a-kind Wicker Park retreat. Spend your days exploring award-winni ...
From $544 per night (USD)VRBO
From $266 per night (USD)VRBO
United Center 3BD Apt with Parking and Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Discover this modern 3-bed apartment, ideally situated near Chicago's United Center. This spacious retreat off ...
From $266 per night (USD)VRBO
From $394 per night (USD)VRBO
Super Paradise Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern and luxurious, open plan, LARGE full equipped back yard also included, located near Midway Airport and 12 minutes ...
From $394 per night (USD)VRBO
From $1839 per night (USD)VRBO
5,000 Sq Ft Luxury Chicago Loft - Prime River North Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to an incredible 5,000-square-foot loft in the heart of Chicago’s River North neighborhood. Designed for groups ...
From $1839 per night (USD)VRBO
From $926 per night (USD)VRBO
Luxury Duplex • 4 bedrooms, 3 Bath• Private Speakeasy• Outdoor Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
About this space Experience Casa Sacramento Social Club, a boutique Humboldt Park duplex designed for unforgettable gath ...
From $926 per night (USD)VRBO
From $551 per night (USD)VRBO
Historic Humboldt Park Flat Workspace + Patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay at Casa Sacramento Gallery House, a boutique Humboldt Park residence blending historic Chicago character with thoug ...
From $551 per night (USD)VRBO
From $236 per night (USD)VRBO
Rooftop, West Loop Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Very spacious unit over a boutique shop. No other tenants in the building with your very own private rooftop d ...
From $236 per night (USD)VRBO
From $268 per night (USD)VRBO
Sunny 3BR - 1Gb Fiber WiFi - EV Charger - Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
About this space Bright, modern 3BR/1.5BA home in Chicago—built for remote work and easy stays. Sun-filled, modern decor ...
From $268 per night (USD)VRBO
From $341 per night (USD)VRBO
East Pilsen Palace | Spacious 4BR • Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your modern Chicago retreat, thoughtfully designed for comfortable mid-term stays. This spacious 4-bedroom, 2 ...
From $341 per night (USD)VRBO
From $190 per night (USD)VRBO
Boutique King Room at Hotel Blake Near Millennium Park & Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Chicago's historic Printer's Row neighborhood, Bluegreen Vacations Hotel Blake blends timeless architecture w ...
From $190 per night (USD)VRBO
From $1354 per night (USD)VRBO
Luxury Humboldt Park Home Speakeasy + Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Casa Sacramento Some places offer a beautiful stay. Others offer a story worth becoming part of. Welcome t ...
From $1354 per night (USD)VRBO
From $135 per night (USD)VRBO
Beautiful, furnished condo with great view in luxurious River North high rise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Super host (on another platform) and now looking forward to hosting here on VRBO! This is the perfect home base for you ...
From $135 per night (USD)VRBO
From $152 per night (USD)VRBO
Cozy 1-bedroom apartment in beautiful Chicago with AC and gym access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a recently renovated spacious convertible one bedroom /studio apartment on the lakefront of Chicago with steps t ...
From $152 per night (USD)VRBO
From $149 per night (USD)VRBO
Bright City Condo w/Balcony, in-unit WD, secure outdoor dog run, Near Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property is spacious and luxurious with its own private balcony and in unit washer and dryer, walk in closet, wood ...
From $149 per night (USD)VRBO
From $663 per night (USD)VRBO
Entire Home in Historic Logan Square with private backyard, parking available.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Kick back & relax in this calm & stylish space! Perfect for families & large groups. I built and designed my home it's b ...
From $663 per night (USD)VRBO
From $244 per night (USD)VRBO
Mid-Century Modern 2 BD APT | Walk to Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience stylish comfort in this beautifully designed, mid-century modern apartment in the heart of Wrigleyville. Enjo ...
From $244 per night (USD)VRBO
From $858 per night (USD)VRBO
4BR Apt Same Floor Combo Group Stays Top Amenities
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Perfect for your next group trip or corporate offsite, 'The Pop' offers two same-floor apartments for the ulti ...
From $858 per night (USD)VRBO
From $241 per night (USD)VRBO
Edgewater Chic Apt: Near Beach & Eats
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 4 bedrooms, and is ste ...
From $241 per night (USD)VRBO
From $266 per night (USD)VRBO
Beautiful 4 bedroom 2 bath pet friendly Chicago brick bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy your stay at this Chicago style brick bungalow. Well cleaned updated 4 bedroom 2 bath. Near shopping, the universi ...
From $266 per night (USD)VRBO
From $682 per night (USD)VRBO
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Chicago at this condo. With 3 bedrooms featuring a king, queen, and full bed, this tranquil ...
From $682 per night (USD)VRBO
From $809 per night (USD)VRBO
Luxury Designer Penthouse Combo | NW | 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 $809 per night (USD)VRBO
From $537 per night (USD)VRBO
Loyola Lookout – Sporty 3BR Apt Steps from Loyola & Lake w/ Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sporty Style Meets City Comfort – Steps from Loyola, the Lake & the L! Welcome to your home base in Chicago’s vibrant Ro ...
From $537 per night (USD)VRBO
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 $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 $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 $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 $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 $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 $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 $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)VRBO
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)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 $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 $183 per night (USD)VRBO
Chicago 2BD 2BA Apartment Perfect for Families
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Discover the vibrant spirit of Chicago from this stylishly renovated apartment in the heart of Pilsen. Wake up ...
From $183 per night (USD)VRBO
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 $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 $291 per night (USD)VRBO
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)VRBO
From $471 per night (USD)Expedia
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)Expedia
From $594 per night (USD)VRBO
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)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 $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 $296 per night (USD)Expedia
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)Expedia
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 $188 per night (USD)VRBO
Open Loop 2BR w/ Lounge & Gym, nr Chicago Riverwalk, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this pretty two bedroom Blueground apartment. You’ll love coming h ...
From $188 per night (USD)VRBO
From $225 per night (USD)VRBO
Long-Term Stays | 1 Garage Parking | Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to our vacation home! Nestled in the heart of the city, it offers the perfect blend of sophistication ...
From $225 per night (USD)VRBO
From $337 per night (USD)Expedia
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)Expedia
From $146 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 $146 per night (USD)VRBO
From $289 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 $289 per night (USD)Expedia
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 $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 $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 $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