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Holiday rentals with a patio in Downtown Chicago

Find and book unique rentals with patio on Airbnb

Top-rated rentals with patio in Downtown Chicago

Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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Guest house in Chicago

4.92 out of 5 average rating, 13 reviews

Private Coach House / Easy Commute

Located in the vibrant neighborhood of Logan Square, known for its hip atmosphere, tree-lined streets, and diverse dining scene, this private apartment is a perfect home away from home for your visit to the Windy City. Whether you're a culinary enthusiast or just looking to whip up a quick snack, you'll find everything for your cooking needs. Convenient public transportation, you can access all that Chicago has to offer. 10 mins walk to the train to get to either downtown Chicago or O’Hare.

11–18 Sep

$225 SGD per night

Guest favourite

Flat in Oak Park

4.91 out of 5 average rating, 104 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!

23–30 Sep

$169 SGD per night

Guest favourite

Flat in Chicago

5.0 out of 5 average rating, 26 reviews

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.

12–19 Jan

$252 SGD per night

Guest favourite

Flat in Logan Square

4.89 out of 5 average rating, 18 reviews

Funky Logan Lair

This gem is located in West Logan in the heart of everything Logan has to offer. The space is the basement unit of an owner-occupied single-family home with private entrance. One bedroom unit with a queen-size bed and living room with connecting kitchenette & bathroom with stand-up shower. The space includes a full size washer and dryer. Located next to the 606 Trail. Private entrance, Easy access to CTA and Divvy Bike Rentals, Free Wi-Fi, Fridge, microwave, toaster & Nespresso(with pods)

24–29 Jan

$161 SGD per night

Guest favourite

Apartment in Gold Coast

4.96 out of 5 average rating, 56 reviews

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

22–29 Jul

$724 SGD per night

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 34 reviews

Fulton House #1 - Studio Only

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.

27 Jul – 3 Aug

$275 SGD per night

Guest favourite

Apartment in Little Italy

4.96 out of 5 average rating, 120 reviews

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.

25 Jun – 2 Jul

$426 SGD per night

Guest favourite

Flat in Chicago

4.91 out of 5 average rating, 33 reviews

Private City Hideaway

Park in the private garage and walk to restaurants, coffee, bars , cafes and shopping. 10 minutes to the train! All outside your front door from this entirely private extra large one bedroom city apartment. Well appointed kitchen, free laundry, wi-fi, heat and air cond. No parking worries with included garage parking!! Click SHOW MORE - for detailed location information - Click SHOW MORE Wrigley Field 8 minutes Uber 15 public transport 30 walking NOTE: no smokers no visitors

16–23 Sep

$189 SGD per night

Guest favourite

Flat in Edgewater

4.8 out of 5 average rating, 5 reviews

Lovely Lake Side Apartment

Enjoy a stylish experience at this centrally-located place. My studio apartment is right off of Lake Shore Drive. Across the street from Hollywood beach, a 4 minute walk. The 147 bus stop is right outside the apartment, which gets you downtown in 30 mins and the red line is a short 5-7 minute walk. The apartment is on the 12th floor with an amazing view of the city. The space is equipped with coffee station, records, books, art, and a great pantry of spices for those that enjoy cooking.

5–12 Oct

$173 SGD per night

Flat in Near South Side

4.78 out of 5 average rating, 58 reviews

McCormick 2B/2Ba for up to 6 guests/private Patio

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Private patio • City skyline view • 2 shifts Security officers in the building • Comfortable stay for up to 6 guests at a time • 2 Queen size beds + Sofa bed for the extra 2 guests • Access to the Gym • Dedicated Internet • 4K smart HDTVs in ALL ROOMS(Netflix) • Fully stocked kitchen with Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

12–19 Jan

$168 SGD per night

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 100 reviews

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.

2–9 Jan

$567 SGD per night

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 32 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!

10–17 Jan

$137 SGD per night

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Popular amenities for rentals with patio in Downtown Chicago

Free parking on premises

Air conditioning

Flat rentals with a patio

Flat in Chicago

4.87 out of 5 average rating, 106 reviews

Idyllic Lakefront Sanctuary W/ Unforgettable Vista

28 Jun – 5 Jul

$504 SGD per night

Guest favourite

Flat in Lincoln Park

4.87 out of 5 average rating, 272 reviews

Historic Old Town Flat - Minutes from Downtown!

10–17 Jun

$344 SGD per night

Guest favourite

Flat in Chicago

5.0 out of 5 average rating, 7 reviews

The Downtown Oasis (2BD / 2BA)

10–17 Feb

$429 SGD per night

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 57 reviews

*BRAND NEW* Lincoln Park GEM

1–8 Nov

$219 SGD per night

Guest favourite

Flat in Forest Park

4.99 out of 5 average rating, 90 reviews

Sunny 1 bedroom apartment 1 block from restaurants

23–30 Jul

$160 SGD per night

Flat in Chicago

5.0 out of 5 average rating, 4 reviews

Fantastic West Loop 2 bedroom

11–18 Nov

$468 SGD per night

Guest favourite

Flat in Logan Square

4.98 out of 5 average rating, 63 reviews

Colorful & Peaceful Boho-Chic Unit in Logan Square

29 Dec – 5 Jan

$211 SGD per night

Guest favourite

Flat in Chicago

5.0 out of 5 average rating, 5 reviews

Gold Coast Pristine Paradise 3BR/2BA. Free Parking

29 Dec – 5 Jan

$826 SGD per night

House rentals with a patio

Guest favourite

Home in Chicago

5.0 out of 5 average rating, 11 reviews

Cubby Blue home - Wrigley ~Free Parking~

22–29 Jan

$268 SGD per night

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 88 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

2–9 Mar

$154 SGD per night

Guest favourite

Home in Chicago

4.95 out of 5 average rating, 19 reviews

Spacius unit in historic gem

6–13 Nov

$233 SGD per night

Guest favourite

Home in Chicago

4.98 out of 5 average rating, 55 reviews

2BD/1 BA with summer patio in quiet Roscoe Village

23–30 Dec

$290 SGD per night

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 71 reviews

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

15–22 Aug

$467 SGD per night

Guest favourite

Home in The Loop

5.0 out of 5 average rating, 52 reviews

Architect's Family Friendly Oasis | 4bd/3ba I Luxe

18–25 Nov

$1,126 SGD per night

Guest favourite

Home in Chicago

4.97 out of 5 average rating, 75 reviews

Cozy/Spacious WFH Family Friendly w Permit Parking

27 Apr – 4 May

$271 SGD per night

Guest favourite

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

23–30 Sep

$228 SGD per night

Apartment rentals with a patio

Guest favourite

Apartment in Chicago

4.98 out of 5 average rating, 104 reviews

Interior designer duplex 2bd 2bath w/ prvt office

5–12 Nov

$413 SGD per night

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 101 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

4–11 Sep

$413 SGD per night

Apartment in Chicago

4.83 out of 5 average rating, 178 reviews

Can't Beat This 2min Walk to Wrigley!

26 Nov – 3 Dec

$737 SGD per night

Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 129 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

1–8 Apr

$1,062 SGD per night

Apartment in Chicago

4.82 out of 5 average rating, 187 reviews

Chicago River West 4 Bedroom / 3 Bathroom

21–28 Jul

$1,047 SGD per night

Apartment in Chicago

4.82 out of 5 average rating, 309 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

27 Dec – 3 Jan

$345 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

23–30 Jan

$171 SGD per night

Guest favourite

Apartment in Chicago

4.99 out of 5 average rating, 75 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

7–14 Jun

$418 SGD per night

Destinations to explore