Vacation rentals with a fire pit in Chicago River

A spacious living area showcases warm wooden floors and a dark brown accent wall. A blue sofa is complemented by colorful cushions, while a wooden coffee table sits in front. Artwork and decorative pieces adorn the walls, and natural light filters through large windows.

4.92 out of 5 average rating, 264 reviews

iKlektik House Chicago/BlueJay

A Space perfect for Two Adults with warm heated floors and amazing craftsmanship + artwork. Custom made built-in king size bed. Large custom kitchen, butcher block and claw foot tub in bathroom. Not suitable for infants/children. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM CLOSE TO THE UNITED CENTER New restaurants and neighborhood favorites, along with cocktail bars and music venues. Metra, Cta {buses and trains} close by. Metra: Western & Hubbard Free Street Parking Right Out Front!

4.96 out of 5 average rating, 394 reviews

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

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.

Superhost

4.82 out of 5 average rating, 233 reviews

The Lakefront Lookout (Rooftop Deck • Gym)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city!

An expansive rooftop patio is showcased, featuring woven outdoor couches with blue cushions arranged around a glass-top table. The city skyline is prominently visible, with notable buildings punctuating the clear blue sky, complemented by touches of lush greenery.

4.98 out of 5 average rating, 120 reviews

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

4.99 out of 5 average rating, 100 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.

4.84 out of 5 average rating, 114 reviews

Private Roofdeck! Location! Parking! Amazing home!

Large Bucktown home with plenty of space for the whole family! Your group will have the best stay in the perfect location to explore all that Chicago has to offer. Steps away from the 606 walking trail and one block from the Blue Line. This home is situated on a beautiful tree lined street with charming bungalows highlighting Bucktown architecture. The home offers 2 floors of living space with a large kitchen, dining room, living room and 3 bedrooms. Custom bath with w/d. Parking included!

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

4.95 out of 5 average rating, 175 reviews

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

*Due to AirBnB new changes in fee disclosure, 18% of the daily rate you see goes to Airbnb* 1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (2 Queens) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. A parking space in the rear allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions. NO CHORES!

4.94 out of 5 average rating, 278 reviews

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

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.

4.98 out of 5 average rating, 150 reviews

A contemporary living space features a comfortable gray sofa adorned with pillows and a cozy throw. A dining table is set for four, with white plates and light floral arrangements. Large windows with sheer curtains allow natural light to brighten the room.

Townhouse in Chicago

𓃥Wicker Cozy Corner w/Parking on site

Welcome to our charming Wicker Park getaway! Located just a 5-minute stroll from the Damen blue line stop, our cozy abode offers the perfect blend of convenience and comfort. Enjoy peace of mind with driveway parking. Explore the vibrant neighborhood with ease – you're just a short walk away from coffee shops, restaurants, bars, unique shopping boutiques, and so much more. Whether you're here for business or leisure, our prime location ensures you're never far from the action.

A modern living area features a contemporary design with a stylish gray sofa and brown leather chairs. A sleek, geometric area rug sits beneath a coffee table, while framed black-and-white photographs line the walls. Large windows allow natural light to illuminate the space.

4.96 out of 5 average rating, 119 reviews

Rooftop Skyline | 5 Ensuites | Games | DT 14 mins

The Monticello ~ Rooftop deck, skyline views, game room, 5 bedrooms w. ensuite bath! ★ "Beautiful, well appointed, and has thoughtful details." ☞ Fully equipped + stocked kitchen ☞ Game room w/ ping pong + arcades ☞ Dedicated workspace + 1 Gig WiFi ☞ Parking → garage (2 cars) ☞ Indoor electric fireplace ☞ Multiple smart TVs (5) ☞ 3 separate bar areas 14 mins → Downtown Chicago 22 mins → Chicago Midway International Airport ✈

4.97 out of 5 average rating, 178 reviews

Condo in Chicago

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.

The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.