
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.

NorthSide Chicago duplex 5-BD,2King size-free park
5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

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.

English garden apt. in the heart of Lincoln Park
Welcome to this new, totally furnished apartment in the heart of East Lincoln Park…only a 3 minute walk to the Lincoln Park Zoo! Apartment has been completely renovated with high finishes throughout. Living room boasts a 50” television with Dish TV, internet and a queen sleeper sofa! Gourmet kitchen with granite counter tops with an eat-in bar height counter top. Truly gourmet kitchen! Bedroom with en-suite European styled bathroom. Wall mounted television in the bedroom. In unit laundry.

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.

Lincoln Pk-Kingbed-fast WIFI-Parking-crib-roofdeck
A Wonderful 2 bedroom Airbnb in the Superhot Lincoln Park neighborhood on a block where homes sell from 5 million to 12.5 million dollars. The apartment was totally renovated adding new furniture, 50-inch High-Definition Flatscreen in the Livingroom, a fully stocked kitchen, superfast wifi, parking space, rooftop deck, Patio, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop. Pack-in-play, highchair, kids. Millennium Pk, Navy Pier, Mag Mile, Museum.

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.

Old Town/Gold Coast Masterpiece (+private rooftop)
Chicago's top getaway spot! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Privacy is hard to beat in this beautiful courtyard! - Luxurious interior design - Spacious rooftop for lounging - Extremely Fast WiFi - Pillow-top Bamboo mattresses - State-of-the-art kitchen - Exceptional workspace - 5-10 minute walk from red line (CTA L) We look forward to hosting you!

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.

50th Floor Mag Mile Views, Balcony, Pool, Gym
The Penthouses at Grand Plaza PH#12: Towering 50 stories above Downtown Chicago, this luxury unit features floor-to-ceiling windows and breathtaking skyline views. Enjoy sunsets, unmatched location, and true urban living. Walk Score of 100 with a grocery store in the building. Amenities include a fitness center, outdoor pool, kitchens, and business center. The city is at your feet—experience Chicago in style.

Steps to Clark St in the Heart of Andersonville
Enjoy local living on the 1st floor of our classic Chicago 2-flat with modern touches and free street parking. Our location is unbeatable, just a few buildings off of Andersonville's famous Clark Street! We live upstairs, maintain the unit ourselves, and are glad to answer questions. You can easily spend your whole stay in Andersonville or explore our iconic city via quick Uber rides or public transportation.

Modern 3BR with Private Rooftop & Free Parking
A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.
Popular amenities for rentals with patio in Chicago
Flat rentals with a patio

Wicker Park Walk-Up Condo

Pristine Chicago Home | 3BD |2BA |Free Parking (2)

King Sleep Number Bed – No Cleaning Fee

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

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

Bright KNG+QN/near DT/walk to restaurants & bars

Bucktown Garden Suite 7 min walk to train

Wicker Park Historic, Art-Filled, Urban Oasis #1
House rentals with a patio

Division St Designer Home In Heart of Wicker Park

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Unique porcelain-enamel paneled "Lustron" home

BoHo House - A Chic, 1903 Chicago Workers Cottage

Victorian House in Heart of Rogers Park

Windy City White House (3br/2ba)

Chicago getaway for two!

Centrally Located, Apt. w/ Kitch. & Parking for 4
Apartment rentals with a patio

Int. Designer’s Lakeview Duplex w/private backyard

Can't Beat This 2min Walk to Wrigley!

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

Modern Chicago Movie Themed Apt

Large Remodeled Home in Lincoln Park, Sleeps 12!

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Wicker Park/Bucktown condo with outdoor patio

Private hot tub - King bed suite - Free parking
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 | $193 SGD | $199 SGD | $227 SGD | $238 SGD | $244 SGD | $248 SGD | $223 SGD | $226 SGD | $202 SGD | $193 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
Destinations to explore
- Platteville Holiday rentals
- Downtown Chicago Holiday rentals
- Indianapolis Holiday rentals
- Southern Indiana Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Windsor Holiday rentals
- Rentals with a fireplace Chicago
- Bed and breakfasts Chicago
- Rentals with a sauna Chicago
- Townhouse rentals Chicago
- Family-friendly rentals Chicago
- Private suite rentals Chicago
- Loft rentals Chicago
- Waterfront rentals Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Rentals with lake access Chicago
- Smoking-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Fitness-friendly rentals Chicago
- Lakehouse rentals Chicago
- House rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Flat rentals Chicago
- Mansion rentals Chicago
- Luxury rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Beachfront rentals Chicago
- Serviced apartment rentals Chicago
- Guest house rentals Chicago
- Boutique hotels Chicago
- Rentals with beach access Chicago
- Rentals with pools Chicago
- Rentals with a patio Cook County
- Rentals with a patio Illinois
- Rentals with a patio United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- 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
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- University of Chicago
- Naval Station Great Lakes
- Things to do Chicago
- Food and drink Chicago
- Sightseeing Chicago
- Art and culture Chicago
- Nature and outdoors Chicago
- Sports activities Chicago
- Tours Chicago
- Things to do Cook County
- Sports activities Cook County
- Tours Cook County
- Art and culture Cook County
- Food and drink Cook County
- Nature and outdoors Cook County
- Sightseeing Cook County
- Things to do Illinois
- Nature and outdoors Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Tours Illinois
- Sports activities Illinois
- Things to do United States
- Food and drink United States
- Wellness United States
- Tours United States
- Art and culture United States
- Sightseeing United States
- Sports activities United States
- Nature and outdoors United States
- Entertainment United States






