
Vacation rentals with a patio in Chicago Loop
Find and book unique accommodations with an outdoor patio on Airbnb
Top-rated accommodations with an outdoor patio in Chicago Loop
Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

Blue Brick Apartment in Bridgeport - Park for Free
-600 sq.ft apartment / 2nd floor / Patio Deck -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

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.

Lovely top floor 2BR/2BA, steps from everything!
BEST LOCATION IN LOGAN SQUARE/AVONDALE with garage parking! 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.

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

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

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.

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.

Fun & cozy getaway w/POOL/game room/FREE parking
Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

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.

Downtown Mich Ave #10 | gym+rooftop
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Double bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

1 bed apartment + futon room bridgeport
Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.
Popular amenities for Chicago Loop accommodations with an outdoor patio
Apartment rentals with a patio

Modern 3BR with Private Rooftop & Free Parking

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

Andersonville's Secret Garden: 2 beds, 1 bath

Sunny 1 bedroom apartment 1 block from restaurants

South Loop 2BR Near McCormick & Lakefront w/ Patio

Balcony, Gym, 1 Garage Parking, Sleeps 12!

Logan’s Cozy Inn.

Top Rated Stay with Free Parking+King Beds+Laundry
House rentals with an outdoor patio

3BD Home Mins from Airport | Free Wi-Fi + Parking

Modern Boho house in Lombard 7 min to Metra

Unique porcelain-enamel paneled "Lustron" home

BoHo House - A Chic, 1903 Chicago Workers Cottage

Entire first floor in Lincoln Square!

Victorian House in Heart of Rogers Park

Boho Chic Coach House 30Min to downtown W/ Parking

Clean & Comfy, Central Loc. & Parking, Sleeps 4
Condo rentals with a patio

Christmas in the City- Holiday Duplex in Lakeview

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Modern Chicago Movie Themed Apt

Tri-Taylor/Medical Dist. near West Loop

Spacious 4 Bedroom Condo

Chic Home! Walk to Nightlife-Comedy-Restaurants!
When is the best time to visit Chicago Loop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $222 CAD | $223 CAD | $247 CAD | $309 CAD | $347 CAD | $410 CAD | $399 CAD | $382 CAD | $350 CAD | $344 CAD | $304 CAD | $252 CAD | 
| 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 vacation rentals with a patio in Chicago Loop

Total vacation rentals
Explore 270 vacation rentals in Chicago Loop

Nightly prices starting at
Chicago Loop vacation rentals start at $56 CAD per night before taxes and fees

Verified guest reviews
Over 8,570 verified reviews to help you choose

Family-friendly vacation rentals
130 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 150 rentals that welcome pets

Vacation rentals with a pool
210 properties feature pools

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wifi availability
270 of Chicago Loop vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chicago Loop rentals

4.8 Average rating
Chicago Loop stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chicago Loop’s top spots, include Millennium Park, Shedd Aquarium, and Willis Tower
Destinations to explore
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 - Rentals with a patio United States
 
- Lincoln Park
 - Millennium Park
 - Wrigley Field
 - United Center
 - Navy Pier
 - Six Flags Great America
 - 875 North Michigan Avenue
 - Humboldt Park
 - Shedd Aquarium
 - Guaranteed Rate Field
 - Oak Street Beach
 - The Field Museum
 - Wicker Park
 - Garfield Park Conservatory
 - Lincoln Park Zoo
 - Frank Lloyd Wright Home and Studio
 - Brookfield Zoo
 - Museum of Science and Industry
 - Willis Tower
 - Illinois Beach State Park
 - Washington Park Zoo
 - The Beverly Country Club
 - Raging Waves Waterpark
 - The 606