
Holiday rentals with a patio in Chicago
Find and book unique rentals with patio on Airbnb
Quick stats about holiday rentals with a patio in Chicago

Total holiday rentals
Explore 4,290 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 311,070 verified reviews to help you choose

Family-friendly holiday rentals
2,810 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,560 rentals that welcome pets

Holiday rentals with a pool
530 properties feature pools

Rentals with dedicated workspaces
3,140 properties have a dedicated workspace

Wifi availability
4,220 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
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.

Paradise on the Boulevard!
Amazing 2 bedroom garden apartment, located in the heart of the highly desirable Logan Square. This luxurious space with heated polished concrete floors & spa inspired bathroom is situated on the Historic Logan Boulevard, just steps from CTA Blue Line. Fabulous restaurants and coffee shops across the street. The apartment has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Peace, convenience & excitement are right here.

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.

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.

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking
Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

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

Evanston 2BR 2Bth 1 Blk to Beach

King Sleep Number Bed – No Cleaning Fee

Sunny 1 bedroom apartment 1 block from restaurants

In the Heart of Andersonville-Steps from Clark St.

Downtown Mich Ave #10 | gym+rooftop

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Colorful Bucktown Garden Apartment

Blue Brick Apartment in Bridgeport - Park for Free
House rentals with a patio

Beautiful 4 BR Family Home near Wrigley

NEW! 3BR/2.5B Duplex in Noble Sq

The Ashlin House.

Entire first floor in Lincoln Square!

Private Downtown Retreat with Rooftop Oasis

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

Kid friendly 2 bedroom w/ private office

My Cozy Casa in Pilsen
Apartment rentals with a patio

Int. Designer’s Lakeview Duplex w/private backyard

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Chicago Oasis | Spa Bath, Patio & Fireplace

Logan Square Beauty with 2 Bedrooms W/parking

Modern Chicago Movie Themed Apt

Wrigleyville Updated Condo with Free Parking

Wicker Park/Bucktown condo with large balcony

Chic Home! Walk to Nightlife-Comedy-Restaurants!
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $175 SGD | $178 SGD | $204 SGD | $200 SGD | $228 SGD | $239 SGD | $245 SGD | $249 SGD | $224 SGD | $227 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 |
Destinations to explore
- Indianapolis Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Downtown Chicago Holiday rentals
- Ann Arbor Holiday rentals
- Windsor Holiday rentals
- Grand Rapids Holiday rentals
- Rentals with an accessible-height bed Chicago
- Serviced apartment rentals Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Waterfront rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a fireplace Chicago
- Townhouse rentals Chicago
- Guest house rentals Chicago
- Rentals with lake access Chicago
- Loft rentals Chicago
- Rentals with a sauna Chicago
- Fitness-friendly rentals Chicago
- Private suite rentals Chicago
- Rentals with an EV charger Chicago
- Smoking-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Lakehouse rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with a balcony Chicago
- Luxury rentals Chicago
- Flat rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Beachfront rentals Chicago
- Rentals with beach access Chicago
- Boutique hotels Chicago
- Mansion rentals Chicago
- House rentals Chicago
- Bed and breakfasts Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with a patio Cook County
- Rentals with a patio Illinois
- Rentals with a patio United States
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- Chicago River Walk
- The Field Museum
- Shedd Aquarium
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Beachwalk Vacation Rentals
- Washington Park Zoo
- Things to do Chicago
- Sightseeing Chicago
- Food and drink Chicago
- Sports activities Chicago
- Nature and outdoors Chicago
- Tours Chicago
- Art and culture Chicago
- Things to do Cook County
- Tours Cook County
- Nature and outdoors Cook County
- Food and drink Cook County
- Sports activities Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Things to do Illinois
- Sports activities Illinois
- Sightseeing Illinois
- Tours Illinois
- Art and culture Illinois
- Food and drink Illinois
- Nature and outdoors Illinois
- Things to do United States
- Nature and outdoors United States
- Tours United States
- Sightseeing United States
- Sports activities United States
- Entertainment United States
- Art and culture United States
- Food and drink United States
- Wellness United States







