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Holiday rentals with outdoor seating in Near North Side

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Near North Side

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

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Top guest favourite
A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.
Guest house in Little Italy
4.99 out of 5 average rating, 916 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Top guest favourite
Flat in Wicker Park
4.97 out of 5 average rating, 293 reviews

Stylish First Flr. Studio. Best Location Division+Hermitage.

Clean! Private! Studio located in the popular Ukrainian Village. This quiet unit is located in a charming 19th century pink brick Victorian cottage. It is a great retreat from work or play when visiting Chicago. This welcoming space features modern amenities, stylish decor with unique artwork, tall ceilings and an inviting color palette. Hermitage House Studio a perfect home away from home with in unit laundry, cable with On Demand and green filled backyard patio perfect for sipping your morning coffee or tea. Need 2nd space same building? Check out airbnb.com/h/chicago-hermitage-loft2 This private –very hip studio apartment - completely renovated and newly decorated is set up like a posh hotel suite with all the amenities of home!! Used for guests only this cozy and modern first floor apartment is set in an 1892 vintage brick cottage with a beautiful outdoor rear patio on a quiet tree lined street! This richly colored designer decorated space with all original artwork has comfort in mind. It has plenty of seating including a comfortable leather sofa, a cool desk area and raised bar. Hardwood floors throughout living space, 9’ ceilings, washer/ dryer, central air and heating, hotel like bathroom with soaking tub and an in unit stacking washer/dryer. Modern white kitchen has granite countertops, quartz sink, gas stove-oven, dishwasher, garbage disposal , microwave. The kitchen has many fun gadgets like French press coffee maker, electric tea pot and more. Everything is available for you to use. The high counter with barstools separates the kitchen from the living/sleeping space. The relaxing bedroom area accommodates 2 with a queen pillow top Serta mattress, great lighting, beautiful Mediterranean blue curtains and storage end tables filled with additional blankets. A full aero bed can accommodate a third person if needed. There is a custom closet system with great storage for personals, shoes and folded clothing. Perfect for a couple or an Airbnb business user! Flat screen TV with cable and movie channels Fast Wi-Fi This unit is located in the quiet first floor rear of this building. The first floor rear patio is yours to enjoy! The upper level deck is private. This unit features a digital locks. You will be able to pick your own code before check-in. I am readily available but will respect your privacy unless you need me. I live in the building (Sometimes out of town) but always accessible by phone or internet if anything is needed but the place is yours to enjoy! Located just steps off bustling Division Street this neighborhood has it all without the fuss of downtown. Within walking distance there are restaurants with cuisines from around the world as well as comfort food. Nightlife options including live music and sports venues. There is boutique shopping, art galleries, a local gym and even a mini Target. This cozy Studio is quick walk from the Division St. Blue-Line train that will get you downtown or to O'hare Airport in minutes. Just two blocks to the Division Blue line running from O’Hare and downtown at the intersection of Division/Ashland/Milwaukee This is a great walking neighborhood but it is easily accessible to many buses, cabs, trains and even the new shared Divvy bike station just a block from the studio. If you choose to drive there is zoned parking permits available- 1 per day. I will happily provide directions to attractions, neighborhoods, great food, groceries, coffee and nightlife

Top guest favourite
The kitchen features modern, streamlined cabinetry and a stainless steel refrigerator. A small dining table with three black stools offers a casual dining space. The kitchen’s layout includes a stove, microwave, and sink, with counter space for meal preparation.
Flat in West Town
4.98 out of 5 average rating, 145 reviews

Cozy Studio in Perfect Location

Recently remodeled English garden studio apartment in the perfect location! Exposed brick with skylights added to this lower level apartment in a great neighborhood! Steps away from the CTA Blue Line train in an area featuring great cafes, bars and restaurants! The apartment was recently renovated and the bed is a Bob-O-Pedic memory foam mattress. If you're coming to Chicago for concerts, sporting events, restaurants, museums or other cultural activities, this location is ideal and pretty chill!

Top guest favourite
Flat in Lincoln Park
4.77 out of 5 average rating, 262 reviews

Rare 1BR Lincoln Park Apt, close to everything!

Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.

Top guest favourite
A light and airy living room is showcased, featuring a comfortable sofa adorned with decorative pillows. Two armchairs are positioned nearby, and a coffee table sits at the center. Natural light filters through two windows, and a large television is mounted on the wall.
Flat in Lincoln Park
4.96 out of 5 average rating, 142 reviews

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.

Guest favourite
A modern living area is shown featuring a light-colored sectional sofa and a wall-mounted television. Natural light enters through large windows, and a small indoor plant adds a touch of greenery. A low coffee table sits in front of the seating area, enhancing the inviting atmosphere.
Flat in West Town
4.97 out of 5 average rating, 117 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.

Top guest favourite
An open living area features a dark leather sofa and a small wooden table atop a vibrant area rug. Natural light floods through two tall windows, framed by wooden shutters. A decorative fireplace is situated to one side, adding to the room's charm.
Flat in Lincoln Park
4.93 out of 5 average rating, 522 reviews

Victorian Guest Suite in Old Town

This private guest suite is the restored 1st floor of my Victorian era single family home. The space has a private ground floor entrance with small patio, located in the “Old Town Historic District”. Decor is Mid Century Modern. Located 1 block north of Sedgwick train station, bus stop across the street, 5 minute walk to the lake, 1/2 hour lakeside walk to downtown. Great restaurants nearby. Only registered guests are allowed on the premises. Please see booking requirements in house rules

Guest favourite
A cozy living area features a comfortable sofa and two round coffee tables positioned on a light-colored rug. The open layout reveals a well-equipped kitchen with white cabinetry and appliances. Natural light pours in through a window, enhancing the warm ambiance.
Flat in West Town
4.97 out of 5 average rating, 250 reviews

Comfy River West, Free Parking

Comfy, sunny 2 bedroom apt with free gated parking. Level 2 EV charging available for electric cars. Beautiful hardwood floors and high ceilings. Fully stocked kitchen with Coffee, tea and snacks. Both bedrooms have ceiling fans. Full length mirror in 1 bedroom and bath. Views of the property gardens and Willis Tower from both bedroom windows. Communal gardens, backyard has table and chairs, BBQ grill and bocce ball. An additional 2 bedroom apt in the same building may also be available.

Guest favourite
A living area features exposed brick walls and polished hardwood floors. A comfortable sofa along with two wooden side tables, each topped with a lamp, is positioned for relaxing. Large windows allow natural light to fill the space, providing views of the outdoors.
Guest suite in River West
4.87 out of 5 average rating, 180 reviews

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

Superhost
A cozy living area showcases a vintage fireplace and a comfortable sofa with red cushions. Natural light filters through a large window, enhancing the inviting ambiance. A coffee table sits in the center, accompanied by a TV on a modern stand and decorative plants.
Flat in Downtown Chicago
4.76 out of 5 average rating, 309 reviews

Secret Gallery on the Park - 2bd/1ba

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love our home because: ✅You are in Chicago’s Gallery district ✅2 blocks from "L" subway ✅Upgraded kitchen & bathroom ✅2 Comfy bedrooms ✅Seamless in-and-out ✅Lots of space ✅Your own personal art gallery in the ART district If you're interested in booking, please see our FAQs below. We look forward to having you at our home!

Top guest favourite
A modern rooftop deck is presented, featuring contemporary seating with vibrant orange cushions arranged around a firepit. Panoramic views of the Chicago skyline are visible, showcasing a mix of architectural styles under a clear blue sky.
Flat in Downtown Chicago
4.92 out of 5 average rating, 172 reviews

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.

Top guest favourite
An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.
Apartment in Fulton Market
4.96 out of 5 average rating, 267 reviews

Designer Loft in Fulton Market with Parking

Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.

Popular amenities for outdoor seating rentals in Near North Side

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Quick stats about holiday rentals with outdoor seating in Near North Side

  • Total holiday rentals

    Explore 340 holiday rentals in Near North Side

  • Nightly prices starting at

    Near North Side holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 14,700 verified reviews to help you choose

  • Family-friendly holiday rentals

    190 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 190 rentals that welcome pets

  • Holiday rentals with a pool

    210 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wifi availability

    340 of Near North Side holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Near North Side rentals

  • 4.9 Average rating

    Near North Side stays are highly rated by guests – averaging 4.9 out of 5!

  • Nearby attractions

    Near North Side’s top spots include 875 North Michigan Avenue, Chicago Riverwalk and Museum of Contemporary Art Chicago

Destinations to explore