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.

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Guest favourite

Flat in Forest Park

4.99 out of 5 average rating, 88 reviews

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.

11–18 Mar

$162 SGD per night

Guest favourite

Flat in Oak Park

4.91 out of 5 average rating, 103 reviews

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

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

1–8 Oct

$196 SGD per night

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 87 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

9–16 Jan

$156 SGD per night

Guest favourite

Flat in Berwyn

4.87 out of 5 average rating, 137 reviews

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

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

9–16 Jul

$141 SGD per night

Guest favourite

Flat in Chicago

4.93 out of 5 average rating, 184 reviews

Spacious & Clean Ukrainian Village 2 Bedroom!

This charming 2 bedroom/1 bath garden apartment is located in Ukrainian Village, a friendly neighborhood on Chicago's near West side! Steps to the restaurants and bars on bustling Division Street, our home is located on a quiet residential side street, so you will have the best of both worlds. Drive to downtown in just 10 - 15 minutes! For any type of traveler, our home is the perfect oasis. Don't miss out, book today! Early Check-Ins and Late Check-Outs are difficult to accommodate.

16–23 Feb

$227 SGD per night

Guest favourite

Flat in Chicago

4.83 out of 5 average rating, 208 reviews

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!

10–17 Jan

$149 SGD per night

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 200 reviews

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).

20–25 May

$355 SGD per night

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 27 reviews

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

Welcome to Jarvis Gardens. A hidden gem in the heart of Chicago's Rogers Park northside neighborhood. Live like a true Chicagoan in this beautifully appointed and recently renovated apartment. Just 1 block to Lake Michigan's Jarvis beach, 1/2 block to Jarvis Square (shops/restaurants/bars/wine stores), and the Jarvis Redline train to Wrigley Field or the 147 bus to the famed Michigan Avenue shopping. No car is necessary for this vacation destination.

2–9 Jan

$176 SGD per night

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 31 reviews

Serene Escape with King Sleep Number Bed, No Fees!

Welcome to our meticulously designed oasis! Relax in luxury on a king-sized Sleep Number bed, refresh in the marbled bathroom with a rain shower, and indulge your culinary passions in the farmhouse-inspired chef's kitchen. Bright, airy, and inviting, our space offers a serene escape. Conveniently located near Belmont CTA Blue Line Station and bus stops, it's the perfect base for your Chicago adventure. Book now for sophistication and comfort!

12–19 Dec

$146 SGD per night

Guest favourite

Flat in Cicero

4.98 out of 5 average rating, 201 reviews

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

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

5–12 Sep

$168 SGD per night

Guest favourite

Guest suite in Wheaton

4.85 out of 5 average rating, 99 reviews

Cozy Wheaton Home

Cozy lower level apartment close to DT Wheaton & Glen Ellyn, restaurants, coffee shops, and shopping. Only 40 minutes outside of the DT Chicago! Train station is walking distance. You'll have the entire lower level of our home to yourself! You'll be able to enjoy your own private entrance, living space, and parking . There is everything you need, coffee, tea, mini fridge, microwave, and a comfy couch with a Firestick TV!

11–18 Feb

$153 SGD per night

Guest favourite

Flat in Chicago

4.87 out of 5 average rating, 271 reviews

Historic Old Town Flat - Minutes from Downtown!

Built in 1886, our "Boland House" offers guests a rare chance to stay in an architecturally significant residence on a beautiful tree-lined street in Historic Old Town district! The original owner was chief of plasterwork projects for the "White City's" 1893 World's Columbian Exposition - combined with modern day conveniences. If you've always wanted to stay in an authentic Chicago Victorian brownstone, you've found it!

28 Jan – 4 Feb

$217 SGD per night