
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.

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.

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!

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.

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.

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.

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!

✨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

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!

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.

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.

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

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
Holiday House Rentals with Outdoor Seating

NEW! 3BR/2.5B Duplex in Noble Sq

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

The Chicago River House – GIANT wall projector!

Cool Quiet Coach House, Private Access + Patio

Victorian House in Heart of Rogers Park

Entire first floor in Lincoln Square!

Private Downtown Retreat with Rooftop Oasis

3 bed/2 bath by United Center w/ private parking
Apartment rentals with outdoor seating

Evanston 2BR 2Bth 1 Blk to Beach

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Modern 3BR with Private Rooftop & Free Parking

The Lakefront Lookout (Rooftop Deck • Gym)

Bridgeport Place -free parking, McCormick-Sox Park

The Bell House: Apartment #1

Walk to UC, Free P, Ping Pong, Sleeps 8
Explore the City from an Elegant, Urban Retreat
Condo rentals with outdoor seating

Studio flat in the heart of Chicago's Gold Coast

NEW luxury Old Town 1-Bedroom condo

Welcome to the Chi! Close to Downtown

Your Chicago Retreat

Two Bedroom w Porch in Wicker Park

Can't Beat This 2min Walk to Wrigley!

Susie's Space. 2BR easy parking & pet friendly

Spacious 4 Bedroom Condo
Other holiday rentals with outdoor seating

Level ◆ Brand New Luxe One Bedroom

Riverfront Views - Smart Home - Simple Check In

Upscale High-Rise Apt · Rooftop Pool + Views

Private rooftop | Breathtaking skyline view

Downtown Chicago Retreat 2BD 2BA Views Gym Rooftop

Chicago Row House Garden Apartmt

ChiCasa Wicker Park Paradise

Newly Remodeled in West Town
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!
Destinations to explore
- Waterfront rentals Chicago River Walk
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- Rentals with breakfast Chicago River Walk
- Family-friendly rentals Chicago River Walk
- Hotel rooms Chicago River Walk
- Rentals with an EV charger Chicago River Walk
- Apartment rentals Chicago River Walk
- Fitness-friendly rentals Chicago River Walk
- Rentals with a washing machine and dryer Chicago River Walk
- Pet-friendly rentals Chicago River Walk
- Rentals with pools Chicago River Walk
- Rentals with a fire pit Chicago River Walk
- Rentals with a hot tub Chicago River Walk
- Rentals with a fireplace Chicago River Walk
- Condo rentals Chicago River Walk
- Serviced apartment rentals Chicago River Walk
- Rentals with an accessible height bed Chicago River Walk
- Rentals with a patio Chicago River Walk
- Rentals with outdoor seating Cook County
- Rentals with outdoor seating Illinois
- Rentals with outdoor seating United States
- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- 875 North Michigan Avenue
- Naval Station Great Lakes
- Indiana Dunes State Park
- Six Flags Great America
- Shedd Aquarium
- The Field Museum
- Humboldt Park
- University of Chicago
- SeatGeek Stadium
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Frank Lloyd Wright Home and Studio
- Union Park
- Donald E Stephens Convention Center
- Washington Park Zoo
- Garfield Park Conservatory





