
Holiday rentals with a patio in Chicago
Find and book unique rentals with patio on Airbnb
Top-rated rentals with patio in Chicago
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

The Metropolitan Retreat (Fitness Center • Sauna)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Wicker Park Walk-Up Condo
Enjoy the best of what Chicago has to offer. Located in the West Town/Wicker Park Neighborhood, steps away from the exciting Division St. and Milwaukee Ave. lined with great neighborhood bars, restaurants, boutiques, etc. Centrally located steps from public transit (The "L" Train/Bus), the expressway, Goose Island, Lincoln Park, & More. Experience one of Chicago's best and most interesting neighborhoods! This apartment is fully furnished with modern touches, a private rear deck & front patio.

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

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.

Fulton House #1 - Studio Only (Nightly)
Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced studio has the business-travel amenities you want: ultra speed wifi, work station, top tier dining options within steps, Nespresso coffee maker, bottled water and more. Paid parking next door $20/day, subject to avail - inquire in advance.

3-bedroom exposed brick in Chicago's Wicker Park
Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Colorful & Peaceful Boho-Chic Unit in Logan Square
Kick back & relax in your home away from home in our stylish, spacious and peaceful abode in the center of the Logan Square neighborhood, close to downtown and the CTA Blue Line. Featuring incredible natural light, modern amenities & beautiful artwork, the apartment is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Milwaukee Avenue, you're only blocks away from local breweries, restaurants, coffee shops and much more!

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.

Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Victorian House in Heart of Rogers Park
Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

Spacious Downtown 3BR with Free Parking
A beautiful, modern, three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'll have the whole space to yourself with easy access to some of the best restaurants in the city, a free parking space on premise, and nearby access to public transportation to quickly get around the city. The interior is recently renovated with new furnishings, and provides a beautiful space to relax and recharge between outings.
Popular amenities for rentals with patio in Chicago
Flat rentals with a patio

Cozy Lincoln Park Studio - Steps to Zoo!

Sunny 1 bedroom apartment 1 block from restaurants

Cozy guest studio, great for couples!

Dtown Penthouse 11+Parking, Gym, Pvt Patio

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Cheerful Oak Park Apartment

Spacious&Modern Condo, Near Dwtn, Secure Parking

Bellwood Getaway
House rentals with a patio

NEW! 3BR/2.5B Duplex in Noble Sq

Modern Boho house in Lombard 7 min to Metra

BoHo House | Chic, 1903 Chicago Workers Cottage

Private Downtown Retreat with Rooftop Oasis

3 bed/2 bath by United Center w/ private parking

WrigleyRoost <5 min to Cubs/train/lake!

Beautiful Chicago Greystone

Kid friendly 2 bedroom w/ private office
Apartment rentals with a patio

Int. Designer’s Lakeview Duplex w/private backyard

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Can't Beat This 2min Walk to Wrigley!

Wrigleyville Inn. Historic Greystone, Free Parking

Spacious 4 Bedroom Condo

Walk to Foster Beach! 3 Bed Andersonville Duplex
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $174 SGD | $176 SGD | $202 SGD | $198 SGD | $226 SGD | $236 SGD | $243 SGD | $246 SGD | $222 SGD | $225 SGD | $200 SGD | $192 SGD |
| 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 |
Quick stats about holiday rentals with a patio in Chicago

Total holiday rentals
Explore 4,250 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 300,260 verified reviews to help you choose

Family-friendly holiday rentals
2,760 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,530 rentals that welcome pets

Holiday rentals with a pool
540 properties feature pools

Rentals with dedicated workspaces
3,150 properties have a dedicated workspace

Wifi availability
4,210 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
Destinations to explore
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach
- Illinois Beach State Park
- Things to do Chicago
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- Art and culture Chicago
- Tours Chicago
- Nature and outdoors Chicago
- Food and drink Chicago
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