
Apartment holiday rentals in Chicago
Find and book unique apartments on Airbnb
Quick stats about apartment rentals in Chicago

Total holiday rentals
Explore 1,080 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 71,960 verified reviews to help you choose

Family-friendly holiday rentals
650 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 270 rentals that welcome pets

Holiday rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
630 properties have a dedicated workspace

Wifi availability
1,060 of Chicago holiday rentals include wifi 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 apartment rentals in Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.

Wrigleyville Condo 2 Blks from Lake & Train
I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

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.

Int. Designer’s Lakeview Duplex w/private backyard
A front door walkup duplex condo in the heart of Lakeview neighborhood. 2bed/2 bath with private office space. Surrounded by restaurants, bars and shops & just steps from the Wellington brown line train stop. Luxurious amenities such as designer toiletries, cooking oils/spices, cafe du monde coffee and various teas. Walk to nearby Wrigley, Lake, Lincoln Park Zoo or stay here and enjoy the private backyard garden with large lounge area, gas fireplace, grill, and 10 person dining table

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

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.

Spacious 4 Bedroom Condo
Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

River North 2-Story · Free Parking · Home Theatre
Two-story River North retreat made for families and business travelers. Free onsite parking, a rare find downtown, plus a fully equipped gourmet kitchen, real dining area, and cozy basement home theatre for movie nights. Unwind in comfortable bedrooms and spa-style baths, then step out to River North’s best dining and nightlife. Hotel Godfrey is under 400 feet away, with the Mag Mile, Chicago River cruises, and Millennium Park all minutes from your door.

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.

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.
Popular amenities for Chicago apartment rentals
Weekly apartment rentals

NEW luxury Old Town 1-Bedroom condo

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Modern/Spacious 2BR/2BA West Town

Chicago Oasis | Spa Bath, Patio & Fireplace

3D Tour! Designer Condo near Logan Square

Your Chicago Retreat

Large Remodeled Home in Lincoln Park, Sleeps 12!

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Pet-friendly apartment rentals

Spacious 3BR • Great for Groups • Fast WiFi • Pets

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

Picture Perfect 3Bed Steps from Train and FLW

Lincoln Square Gem!

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

Two Bedroom w Porch in Wicker Park

Can't Beat This 2min Walk to Wrigley!
Apartment rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

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

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Just remodeled apartment close to airport and mall

"Heart of Evanston" 2br +1Bath-0.6miles to NU

Pond View, Washer Dryer, Non Smoking Community

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £94 | £96 | £110 | £110 | £126 | £133 | £134 | £139 | £122 | £124 | £112 | £106 |
| 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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- 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
- Chicago River Walk
- Humboldt Park
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Union Park
- Frank Lloyd Wright Home and Studio
- Washington Park Zoo
- Garfield Park Conservatory
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