Holiday rentals with outdoor seating near Chicago River Walk

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated outdoor seating rentals near Chicago River Walk

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A cozy living area features a plush green sofa adorned with patterned throw pillows. A textured rug covers the floor, while a wooden staircase leads to the lofted sleeping area. Natural light filters through the window, illuminating the space.
Guest suite in Chicago
4.96 out of 5 average rating, 389 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Top Guest favourite
A bright living area features a comfortable gray sofa with decorative pillows, a round coffee table, and large windows overlooking a private outdoor space. Light wood flooring complements the modern kitchen area, which includes sleek bar stools and stainless steel appliances.
Apartment in Chicago
4.95 out of 5 average rating, 155 reviews

Perfect Spot & Spacious 2BR+2BA | Mapletree Suites

Welcome to Mapletree Suites! Our stylish, clean, and contemporary 2 bed+2 bath suites are located in a boutique building in Chicago’s booming West Loop neighborhood. Keyless entry, blazing fast WiFi, bright white linens, in-unit laundry, 10ft ceilings, balconies, Italian cafe, host on-site, plus much more! Steps from Target store, parks/athletic field, CTA, and close to United Center, world-class restaurants, loop/lakefront, Med District, UIC, corporate offices and highway network. Book today!

Top Guest favourite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Condo in Chicago
4.97 out of 5 average rating, 155 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Top 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.
Apartment in Chicago
4.97 out of 5 average rating, 262 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 spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Chicago
4.94 out of 5 average rating, 276 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.

Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 106 reviews

Luxury Loft Collection 02 - 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!

Superhost
A spacious living area features large windows allowing abundant natural light. Exposed Chicago brick adds character to the space, while hardwood floors extend throughout. A comfortable sectional sofa, a chic armchair, and a tasteful area rug create a welcoming atmosphere. A television and decorative furnishings are also visible.
Apartment in Chicago
4.91 out of 5 average rating, 316 reviews

✨Spacious Centrally Located West Loop Loft✨

✔ FREE Fitness classes at The Barre Code included ✔ FREE STREET PARKING - Msg for more info ✔ PETS ok w/ prior approval ✔ HUGE 1300 sq ft loft style, but walls go to the ceiling ✔ CLEAN & sanitized ✔ Cozy & bright ✔ FAMED, historic Chicago pink brick ✔ Soap & other toiletries included ✔ Bedrooms are in back & quiet ✔ Central Location: -Close to trains & bus -6-10 mins to popular neighborhoods & hot restaurants ⚠️Construction noted in older reviews was completed in Nov '24

Guest favourite
A spacious rooftop deck is featured, showcasing a sectional sofa and colorful lounge chairs. A barbecue grill is positioned nearby, surrounded by planters filled with vibrant flowers. The skyline of Chicago and a glimpse of Lake Michigan are visible in the background under a clear blue sky.
Apartment in Chicago
4.84 out of 5 average rating, 128 reviews

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!

Top Guest favourite
Apartment in Chicago
4.99 out of 5 average rating, 279 reviews

Quaint Comfort Studio Near Downtown/Queen Bed

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Top Guest favourite
A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.
Condo in Chicago
4.9 out of 5 average rating, 190 reviews

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Top 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 Chicago
4.88 out of 5 average rating, 209 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

Top Guest favourite
Condo in Chicago
4.97 out of 5 average rating, 175 reviews

Chicago Oasis | Spa Bath, Patio & Fireplace

Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

Popular amenities for outdoor seating rentals near Chicago River Walk

Quick stats about holiday rentals with outdoor seating near Chicago River Walk

  • Total holiday rentals

    Explore 130 holiday rentals in Chicago River Walk

  • Nightly prices starting at

    Chicago River Walk holiday rentals start at $142 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,790 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Chicago River Walk holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chicago River Walk rentals

  • 4.9 Average rating

    Chicago River Walk stays are highly rated by guests—averaging 4.9 out of 5!

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