
Condo holiday rentals in Chicago
Find and book unique condos on Airbnb
Quick stats about condo rentals in Chicago

Total holiday rentals
Explore 1,010 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $34 NZD per night before taxes and fees

Verified guest reviews
Over 72,460 verified reviews to help you choose

Family-friendly holiday rentals
610 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 280 rentals that welcome pets

Holiday rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
610 properties have a dedicated workspace

Wi-Fi availability
1,010 of Chicago holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chicago rentals

4.8 Average rating
Chicago stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chicago's top spots, include Millennium Park, Wrigley Field, and Lincoln Park
Top-rated condo rentals in Chicago
Guests agree: These condos are highly rated for location, cleanliness and more.

Stylish 2-bedroom flat in Vibrant Bucktown.
* Please be aware the city of Chicago is currently renovating its lead pipes. Construction is inevitable and noise. Its a city there will be noise. Hello and welcome to Bucktown! One of Chicago's most popular neighborhoods. Bucktown is centrally located, just a short commute to downtown and surrounded by the best dining and entertainment options Chicago has to offer. We are also half a mile from the expressway and 1 mile away from the Blue Line which directly connects to O'hare airport.

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking
Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Sunny Top-Floor Uptown Condo Near Lake & Red Line
Bright top-floor Chicago condo with fast WiFi, dedicated workspace, and easy access to Montrose Beach and the CTA. Perfect for remote workers, couples, and travelers looking to experience Chicago like a local. Enjoy a sunny living room, fully equipped kitchen and dining room, spacious primary bedroom, and serene sunroom with a full-size bed. Just steps from the lakefront and a 6-minute walk to the 24/7 Wilson Red Line. Over 1,000 sq. ft. of comfortable living space in historic Uptown.

Lovely top floor 2BR/2BA, steps from everything!
BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Alluring Condo w/ Pri. Prkng Cls to Transit &Beach
Our 3 bedroom and 2 bathroom condo has a perfect open layout for any size group that is traveling together. You'll have a ton of open space to share and feel at home, while also choosing from 3 bedrooms to get some privacy as well. Each bedroom has a queen size bed, while the master bedroom also has its own full size private bathroom. Feel free to stay in and cook with our fully equipped kitchen, enjoy the 65 inch Roku TV, and gather around the very large island.

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Two Bedroom w Porch in Wicker Park
Spacious two bedroom apartment with custom wood shelving and hard wood floors. Bay windows and great natural light. Gorgeous furnished porch for when the weather is nice. Quiet, tree lined street that's close to all the best bars and music venues. Short walk to Milwaukee avenue, two blocks from the Division Street blue line station which runs direct from O'hare, only two stations to downtown.

Modern Izakaya Studio in Wicker Park
The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

Old Town Condo: Private Terrace & Garage Parking
Experience vibrant Chicago from this modern 2-bed, 2-bath Old Town condo. Perfect for families or professionals, it features a private terrace, gourmet kitchen, dedicated workspace, and a rare dedicated parking spot. Soaring 13-ft ceilings and stylish design create a light-filled urban retreat just steps from Lincoln Park, Second City, and North Avenue Beach. Comfortably sleeps 4.

Lincoln Square Gem!
Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. We live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
Enjoy a stylish, fun condo experience on Northalsted, nestled between Wrigley Field and LGBTQ+ Nightlife! A huge street view patio in the front provides a birds eye view of the lively neighborhood below and massive above garage patio in the back provides a lot of outdoor living in the city!
Popular amenities for Chicago condo rentals
Weekly condo rentals

Designer Avondale 2BR w/Easy Parking

Int. Designer’s Lakeview Duplex w/private backyard

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

Susie's Space. 2BR easy parking & pet friendly

3-bedroom exposed brick in Chicago's Wicker Park

Wicker Park/Bucktown condo with large balcony

Modern/Spacious 2BR/2BA West Town

Chic Home! Walk to Nightlife-Comedy-Restaurants!
Pet-friendly condo rentals

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Downtown Park #11 - Mich Ave PH | gym+rooftop

Can't Beat This 2min Walk to Wrigley!

Chicago River West 4 Bedroom / 3 Bathroom

Lincoln Park Hideaway - 5 Min Walk to the Park!

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Picture Perfect 3Bed Steps from Train and FLW
Condo rentals with a pool

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Just remodeled apartment close to airport and mall

Pond View, Washer Dryer, Non Smoking Community

Red Door

Best view and luxury style, Located in Downtown

Lovely 2 Bed 2 Bathroom!

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $213 NZD | $218 NZD | $250 NZD | $250 NZD | $286 NZD | $303 NZD | $305 NZD | $315 NZD | $277 NZD | $283 NZD | $255 NZD | $242 NZD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Destinations to explore
- Indianapolis Holiday rentals
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- Downtown Chicago Holiday rentals
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- Rentals with a home theatre Chicago
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Beachwalk Vacation Rentals
- Garfield Park Conservatory
- Washington Park Zoo
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