
Holiday rentals with outdoor seating in Chicago
Find and book unique rentals with outdoor seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Chicago

Total holiday rentals
Explore 2,670 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 223,230 verified reviews to help you choose

Family-friendly holiday rentals
1,890 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 990 rentals that welcome pets

Holiday rentals with a pool
330 properties feature pools

Rentals with dedicated workspaces
2,240 properties have a dedicated workspace

Wifi availability
2,670 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 outdoor seating in Chicago
Guests agree: these rentals with outdoor seating 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.

Flat in Lincoln Park 2-Flat Central to Everything
Historic, newly renovated flat in the heart of Lincoln Park, with garage! A block from the famous Blues club "Kingston Mines". Close to great bars and restaurants, including Alinea, the only restaurant in Chicago awarded 3 Michelin Stars. A mile to Lincoln Park Zoo, less than 1-1/2 miles to the lake. Beautiful yard (shared with lower unit) has gas grill, patio, deck, and a garage space. Enjoy the Lincoln Park area in this unique home that offers everything you need for your holiday in Chicago.

Private Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

Upscale Home in Lincoln Park Minutes from Downtown
Minutes outside downtown Chicago, built in 1890, this gorgeous fully-remodeled modern Victorian-era row house is located in the heart of Chicago’s historic and vibrant Lincoln Park. One of Chicago’s most affluent neighborhoods! > Walkability score of 98/100 > 4 min walk to the train station, steps to bus stops, short Uber ride to all top Chicago attractions > Across DePaul > Amazing parks & bike trails, free zoo, performing arts, shops, nightlife, spas & some of Chicago’s finest restaurants

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.

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.

Luxury Loft Collection 703 - Terrace - River North
BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

An elegant Chicago Northside Getaway
Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

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

Vintage Elegance Meets Modern Sophistication
Beautiful large 2000+ sqft vintage three bedroom apartment with separate office and two living rooms and formal dining room. This flat has been recently remodeled with modern sensibilities, while keeping the vintage charm. Soaring ceilings and bright light filled rooms transport you to your own private oasis. Easily enjoy one of Chicago’s most engaging neighborhoods within walking distance of many restaurants and unique shops.

Modern 3BR with Private Rooftop & Free Parking
A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Beautiful and spacious West Loop apartment.
This sunny & spacious 2bd / 2ba is the perfect getaway in the epicenter of the bustling Fulton Market neighborhood. Find Chicago’s most eclectic restaurant scene steps from your apartment. Explore the many coffee houses, shops, and galleries the West Loop has to offer. Downtown and Millennium Park are a short "El" ride away. Complimentary assorted coffee, fluffy towels and a beautiful deck await!
Popular amenities for outdoor seating rentals in Chicago
House rentals with outdoor seating

NEW! 3BR/2.5B Duplex in Noble Sq

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

The Chicago River House – GIANT wall projector!

The Ashlin House.

Cool Quiet Coach House, Private Access + Patio

Vintage Designed 3BR Condo Near DePaul University

Entire first floor in Lincoln Square!

Wrigleyville Southport Studio
Apartment rentals with outdoor seating

Evanston 2BR 2Bth 1 Blk to Beach

iKlektik House Chicago/BlueJay

Bright family-friendly Lincoln Square 2-bed 1-bath

Spacious Studio w/Balcony in Bucktown/Wicker Park

The Bell House: Apartment #1

Stylish 2BR Andersonville — Walk to Lake & Cafés

Modern vintage chic steps from Wrigley: park free

Spacious&Modern Condo, Near Dwtn, Secure Parking
Apartment rentals with outdoor seating

Inspired, luxe living in Logan Square on BLVD #1

Chicago Oasis | Spa Bath, Patio & Fireplace

Your Chicago Retreat

Two Bedroom w Porch in Wicker Park

Susie's Space. 2BR easy parking & pet friendly

Spacious 4 Bedroom Condo

Wicker Park/Bucktown condo with large balcony

Stylish 2-bedroom flat in Vibrant Bucktown.
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $180 SGD | $181 SGD | $207 SGD | $208 SGD | $242 SGD | $257 SGD | $260 SGD | $265 SGD | $235 SGD | $244 SGD | $213 SGD | $200 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
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- Rentals with an accessible-height bed Chicago
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- Rentals with outdoor seating Cook County
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- Rentals with outdoor seating 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
- The Field Museum
- Shedd Aquarium
- Chicago River Walk
- Humboldt Park
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Frank Lloyd Wright Home and Studio
- Union Park
- Donald E Stephens Convention Center
- Washington Park Zoo
- Garfield Park Conservatory
- Things to do Chicago
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- Sightseeing Chicago
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