
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

Cozy 1BR + Futon • Deck • Laundry • Private Entry
Located at the geographic center of Chicago with plenty of FREE street parking. The area is very safe and about a 10-min walk to the 35th/Archer Orange Line and just 3 blocks from the Archer bus—both take you downtown within minutes. This lower-level 1BR has a private entrance, spacious queen bedroom, living room with full futon, full kitchen, and private bath. Perfect for solo stays, couples, small families, or work trips. Enjoy your own space with access to a back patio, grill, and laundry.

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!

Millennium park 10 min Free P-Spot&Balcony Sleep 8
FREE & SECURE ONE IN-DOOR PARKING SPOT!!! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences. Bring the whole family to this great place with lots of room for fun.

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.

Hidden Gem - 3 Story House & Pet Friendly!
Cozy & entertaining family -pet friendly property in the heart of Chicago - Lincoln Park. This Smart triplex has a fully-equipped kitchen. Large patio w/ sunset views. 3 bedrooms & 2.5 bathrooms. A Foosball table, 82' TV & BAR to enjoy a night in. This property is perfect to book w/ family or friends. Its spacious yet set up the right way to entertain in one floor, cook in another & sleep without having to deal with noise. Pets: Certain restrictions may apply. It is $35/night per pet

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen
Welcome to our charming home in the peaceful yet centrally located Buena Park neighborhood, housed in an updated antique building. This prime location offers easy access to the Red and Purple train lines, as well as multiple bus routes, making it easy to explore Chicago. You’ll be within walking distance of Wrigley Field, Clark St. bars, Montrose Beach, Lakeview, Boystown, and the iconic Green Mill. A perfect blend of quiet comfort and proximity to Chicago’s best attractions.

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.

Entire first floor in Lincoln Square!
First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!

Cozy Lincoln Park Studio - Steps to Zoo!
This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

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

Wicker Park Walk-Up Condo

Sunny 1 bedroom apartment 1 block from restaurants

King Sleep Number Bed – No Cleaning Fee

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Home in Forest Park Upstairs.

Cheerful Oak Park Apartment

The Green Bungalow: Charming 1-BR apt. with patio

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
House rentals with a patio

Division St Designer Home In Heart of Wicker Park

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

Modern Boho house in Lombard 7 min to Metra

The Sunshine Spot

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

Quiet cul-de-sac with huge fenced in backyard

Chicago getaway for two!

Cozy 2 bedroom house/w garage in Skokie
Apartment rentals with a patio

Int. Designer’s Lakeview Duplex w/private backyard

Convenient & Spacious 3BR Condo w/Free Parking

Welcome to the Chi! Close to Downtown

Renovated 3br Duplex In Logan Square W/parking

Modern Chicago Movie Themed Apt

Spacious 4 Bedroom Condo

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 | $170 SGD | $167 SGD | $191 SGD | $198 SGD | $226 SGD | $236 SGD | $242 SGD | $246 SGD | $222 SGD | $225 SGD | $200 SGD | $191 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
- Indianapolis Holiday rentals
- Downtown Chicago 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
- Beachfront rentals Chicago
- Private suite rentals Chicago
- Family-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Flat rentals Chicago
- Rentals with an EV charger Chicago
- Guest house rentals Chicago
- Rentals with lake access Chicago
- Waterfront rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Townhouse rentals Chicago
- Luxury rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Smoking-friendly rentals Chicago
- Serviced apartment rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with a sauna Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Rentals with a fireplace Chicago
- Mansion rentals Chicago
- House rentals Chicago
- Loft rentals Chicago
- Rentals with pools Chicago
- Villa rentals Chicago
- Lakehouse rentals Chicago
- Rentals with a balcony Chicago
- Boutique hotels Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with beach access Chicago
- Bed and breakfasts 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
- 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
- Things to do Chicago
- Sightseeing Chicago
- Food and drink Chicago
- Tours Chicago
- Art and culture Chicago
- Sports activities Chicago
- Nature and outdoors Chicago
- Things to do Cook County
- Nature and outdoors Cook County
- Sightseeing Cook County
- Tours Cook County
- Food and drink Cook County
- Sports activities Cook County
- Art and culture Cook County
- Things to do Illinois
- Tours Illinois
- Art and culture Illinois
- Food and drink Illinois
- Nature and outdoors Illinois
- Sports activities Illinois
- Sightseeing Illinois
- Things to do United States
- Nature and outdoors United States
- Entertainment United States
- Sports activities United States
- Sightseeing United States
- Wellness United States
- Food and drink United States
- Art and culture United States
- Tours United States






