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 Cicero

4.98 out of 5 average rating, 210 reviews

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.

Superhost

Apartment in Chicago

4.87 out of 5 average rating, 110 reviews

Idyllic Lakefront Sanctuary W/ Unforgettable Vista

From the moment you step into the living room of my lakefront home, your breath will be taken away by the incredible scenery outside of the huge windows. Let the gentle sounds of the lake relax you and clear your mind during your tranquil stay. The interior is just as stunning with professionally designed decor, completely new appliances, & thoughtfully provided amenities. You will want for nothing during your stay and may not want to leave! Don't miss out on a true lakefront gem, book today!

Guest favourite

Apartment in Oak Park

4.92 out of 5 average rating, 108 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!

Guest favourite

Condo in Chicago

4.96 out of 5 average rating, 129 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.

Superhost

Apartment in Chicago

5.0 out of 5 average rating, 4 reviews

Cozy Bungalow Getaway

This comfy, cool, garden-level apartment is nestled in a friendly historic Chicago bungalow neighborhood. It’s close to universities (Northeastern and North Park), LaBagh Woods (hiking/biking trails), Gompers Park pool, park and lagoon, O'Hare Airport (20 mins away) and diverse restaurants and entertainment, some walkable, some a short Uber/Lyft away. Easy expressway, transit and bike trail access. Perfect for solo adventurers, couples, students, visiting families, and business travelers.

Guest favourite

Apartment in Chicago

4.93 out of 5 average rating, 41 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

Guest favourite

Condo in Chicago

4.93 out of 5 average rating, 43 reviews

Spacious Apartment in Chicago

Updated vintage charm in the heart of Lincoln Park. 1000 sqft 1 bedroom + office, 1 bath situated in a three flat condo building . Large living space with huge windows and southern exposure with patio. Come experience a walkers paradise with the lake, shopping, and nightlife all within a short distance. Street parking is plentiful on street and surrounding streets in which I can provide street parking stickers for $5/night. The apartment is my home when not being rented out.

Guest favourite

Apartment in Chicago

4.83 out of 5 average rating, 216 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!

Guest favourite

Condo in Chicago

4.97 out of 5 average rating, 32 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.

Guest favourite

Apartment in Chicago

4.97 out of 5 average rating, 36 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!

Guest favourite

Guest suite in Wheaton

4.83 out of 5 average rating, 108 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!

Guest favourite

Apartment in Lincoln Park

4.87 out of 5 average rating, 276 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!