
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.

Sunny 1 bedroom apartment 1 block from restaurants
This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

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.

Sun drenched 2 bedroom 1 bath with Kitchen & W/D
Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

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.

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.

Grace House | Cozy, contemporary + convenient 2-BR
Make yourself at home in our newly renovated, spacious and immaculately clean 2-bedroom, 1-bath condo — perfect for your next family, work or friends' trip. Located on a tree-lined street in a family-friendly neighborhood and walkable to shops, restaurants, cafes, bars and more. A stone's throw to Southport Corridor/Wrigleyville/Lakeview, Lincoln Square, Roscoe Village and everything the Northside has to offer. Gigabit internet w/ WiFi and everything you need to live and thrive in Chicago.

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

Luxury Loft Collection 01 - Terrace - River North
BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

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).

Charming & Bright Multilevel Townhome with Parking
Plenty of space to spread out and relax! My two level townhome in the hot Old Town neighborhood makes for the perfect relaxation destination for any type of traveler. With workspaces in both bedrooms, a beautiful full-sized kitchen, free parking and laundry on-site, and the best location, you can't beat what my place has to offer. Walk to Wells St, North Ave, Lincoln Park, and the lakefront! You won't want to miss out on this unique opportunity. Book today!
Popular amenities for rentals with patio in Chicago
Flat rentals with a patio

Family-Friendly 2BD/2BA Prime Location (+parking)

NorthSide Chicago duplex 5-BD,2King size-free park

Heart of Andersonville | Quiet | Steps to Clark St

Vibrant & Chic Apt On Quiet St in Andersonville

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Home in Forest Park Upstairs.

Bright & Modern Apt | Steps to Lake, Train, Food

Chicago Penthouse Mid-Century Modern: Logan Square
House rentals with a patio

*King bed *Outdoor Living *Sought-After Area

Modern Boho house in Lombard 7 min to Metra

BoHo House - A Chic, 1903 Chicago Workers Cottage

Boho Chic Coach House 30Min to downtown W/ Parking

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

Chicago Row House Garden Apartmt

Centrally Located, Apt. w/ Kitch. & Parking for 4

Beautiful Chicago Greystone
Apartment rentals with a patio

Welcome to the Chi! Close to Downtown

Can't Beat This 2min Walk to Wrigley!

Spacious 4 Bedroom Condo

Large Remodeled Home in Lincoln Park, Sleeps 12!

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Walk to Foster Beach! 3 Bed Andersonville Duplex

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Wicker Park/Bucktown condo with outdoor patio
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $171 SGD | $168 SGD | $192 SGD | $199 SGD | $227 SGD | $237 SGD | $244 SGD | $248 SGD | $223 SGD | $226 SGD | $201 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 4,570 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 299,900 verified reviews to help you choose

Family-friendly holiday rentals
2,910 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,540 rentals that welcome pets

Holiday rentals with a pool
540 properties feature pools

Rentals with dedicated workspaces
3,330 properties have a dedicated workspace

Wifi availability
4,530 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
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- University of Chicago
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- Nature and outdoors Chicago
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