
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.

Bright & Modern Apt | Steps to Lake, Train, Food
This is the ideal location for your trip to Chicago! Steps from the Red Line Train, Foster Beach, Lake Shore Drive, Lake Front Trail, amazing Restaurants & a quality grocery store. You'll enjoy a clean & spacious 2 bedrooms apartment w/ friendly neighbors, flawless check-in & reserved parking. This place is safe & provides a beautiful & stocked apartment to relax after a busy day in the city. Short walk to Andersonville & Asia on Argyle for wonderful food options. The Riv &Aragon for concerts

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.

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.

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.

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.

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
Popular amenities for rentals with patio in Chicago
Flat rentals with a patio

Evanston 2BR 2Bth 1 Blk to Beach

Lovely, spacious 2bd, 1bath home w/free parking

Beverly Cottage Loft

Vibrant & Chic Apt On Quiet St in Andersonville

Home in Forest Park Upstairs.

50th Floor Mag Mile Views, Balcony, Pool, Gym

Lincoln Pk-Kingbed-fast WIFI-Parking-crib-roofdeck

Fulton House #1 - Studio Only (Nightly)
House rentals with a patio

House Bucktown /wickerPark.

The Architectural Haven

*King bed *Outdoor Living *Sought-After Area

CasaNova Modern City Living

A Wonderful Getaway Home on the North Shore!

California Cottage/4br prime location Logan Square

Big house in the BEST Location!

Boho Chic Coach House 30Min to downtown W/ Parking
Apartment rentals with a patio

Convenient & Spacious 3BR Condo w/Free Parking

Renovated 3br Duplex In Logan Square W/parking

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!

Walk to Foster Beach! 3 Bed Andersonville Duplex

Wicker Park/Bucktown condo with large balcony
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
Destinations to explore
- Platteville Holiday rentals
- Downtown Chicago Holiday rentals
- Indianapolis Holiday rentals
- Southern Indiana Holiday rentals
- Detroit Holiday rentals
- Louisville Holiday rentals
- St. Louis Holiday rentals
- Columbus Holiday rentals
- Cincinnati Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Windsor Holiday rentals
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Rentals with an accessible-height bed Chicago
- Private suite rentals Chicago
- Fitness-friendly rentals Chicago
- Loft rentals Chicago
- Rentals with a sauna Chicago
- Rentals with a balcony Chicago
- Rentals with an EV charger Chicago
- Flat rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Smoking-friendly rentals Chicago
- Rentals with a fireplace Chicago
- Lakehouse rentals Chicago
- Townhouse rentals Chicago
- Family-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with lake access Chicago
- Bed and breakfasts Chicago
- Guest house rentals Chicago
- House rentals Chicago
- Mansion rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Beachfront rentals Chicago
- Boutique hotels Chicago
- Rentals with beach access Chicago
- Waterfront rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Luxury rentals Chicago
- Rentals with pools Chicago
- Serviced apartment rentals 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
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Brookfield Zoo
- Museum of Science and Industry
- University of Chicago
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- Things to do Chicago
- Art and culture Chicago
- Food and drink Chicago
- Sports activities Chicago
- Nature and outdoors Chicago
- Sightseeing Chicago
- Tours Chicago
- Things to do Cook County
- Tours Cook County
- Sports activities Cook County
- Food and drink Cook County
- Nature and outdoors Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Things to do Illinois
- Food and drink Illinois
- Nature and outdoors Illinois
- Tours Illinois
- Sports activities Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Things to do United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Entertainment United States
- Wellness United States
- Sports activities United States
- Sightseeing United States
- Nature and outdoors United States






