Vacation rentals with a patio in North Side

Find and book unique accommodations with an outdoor patio on Airbnb

Top-rated accommodations with an outdoor patio in North Side

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 80 reviews

Adorable Private Edgewater Suite

Cozy exposed brick, garden unit on a quiet street, perfect for relaxing after a night out in the city! Comfy, queen-sized bed, full kitchenette and gated private side entrance so its the perfect spot for your trip to Chicago! We are right by the exciting nightlife of Andersonville and a 10 minute walk to the beach/start of the Lakefront trail. Public Transit is close and easily accessible, the redline "L" can get you downtown in a half-hour train ride. Close to Loyola University, Go Ramblers!

Sep. 28 – Oct. 5

$219 CAD per night

Guest favourite

Apartment 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!

Aug. 24 – 31

$224 CAD per night

Guest favourite

Home in West Rogers Park

5.0 out of 5 average rating, 12 reviews

Hidden Gem on the CHI north side

Take it easy at this unique and tranquil getaway. Close to Northwestern and Loyola for visiting parents. Easy access to public transportation (Red Line). Residential home neighborhood provides ample street parking. Spacious enclosed backyard provides privacy for quiet time. Amenities include grills, patio furniture, and small fire pit for outdoor living. Totally private upstairs unit with WiFi access allows remote working. Upstairs unit is spacious with full eat in kitchen and living room.

Sep. 14 – 21

$249 CAD per night

Guest favourite

Apartment in Logan Square

5.0 out of 5 average rating, 8 reviews

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.

Jan. 2 – 9

$291 CAD per night

Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 31 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

Sep. 16 – 23

$254 CAD per night

Guest favourite

Home in Chicago

4.98 out of 5 average rating, 54 reviews

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

Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/1 bath with a sunny private patio deck in the rear with everything you need for a relaxing getaway in Chicago. It is walking distance to everything you need: grocery store (5 min walk), pharmacy (3 min walk), bars + restos (5 min walk), Brown line station Paulina (9 min walk), Hamlin Park (6 min walk), Wrigley Field (8 min drive). On-street parking is permitted.

Dec. 16 – 23

$299 CAD per night

Guest favourite

Condo 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.

Jan. 11 – 18

$229 CAD per night

Guest favourite

Apartment 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!

Aug. 8 – 15

$257 CAD per night

Guest favourite

Apartment 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.

Dec. 11 – 18

$196 CAD per night

Guest favourite

Guest suite in Wheaton

4.85 out of 5 average rating, 100 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!

Feb. 12 – 19

$168 CAD per night

Guest favourite

Apartment in Lincoln Park

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!

Jan. 28 – Feb. 4

$351 CAD per night

Guest favourite

Apartment in Forest Park

4.85 out of 5 average rating, 111 reviews

Home away from home downstairs

Enjoy a stylish experience at this centrally-located, easy access , ground floor apartment. You will have a fully equipped kitchen, laundry facility outside your back door and super fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation.

Dec. 30 – Jan. 6

$174 CAD per night