
Houses in Chicago
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Top-rated boutique hotel rooms in Chicago
Guests agree: these boutique hotel rooms are highly rated for location, cleanliness, and more.
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Popular amenities for Chicago boutique hotel rooms
Boutique hotel rooms in Chicago

King Room in Theatre District
I had a great stay. Clean, check-in was easy, and the room is conveniently located to many Chicago attractions.

Charming King Bedroom in Loop
Absolutely! Go ahead and send me the Airbnb review you want expanded, and I’ll enhance it with more detail, warmth, or whatever tone you’re going for.

1BD/1BA steps away from local shops, entertainment
A wonderful place, clean, well equipped, friendly, and located in a great neighborhood. We will return the next time we go to Chicago!

Charming Private Room in Downtown
This is wonderfully located , clean and nice place! It is the second time that I stay there and it is still lovely! Thank you!

King Bedroom in Theatre District
Cambria hotel was super convenient. Instructions for check in were clear. Room was as shown in the photos. Super close to everything and easily walkable to the theaters! Will stay again.

Private King Bedroom in Heart of Downtown Chicago
Enjoyed our stay, thank you Paul for having us!

Private King Room in Theatre District
Staff were incredibly helpful during our stay. Checking in and out was super smooth and efficient. The location is super convenient and walkable to many fun activities and restaurants. We didn’t have to be on public transit for more than a half hour for anything we couldn’t walk to.

Bright 1BR w/ shared Roof Deck, close to beach
FANTASTIC Andersonville place to stay, walkable to all the best the neighborhood has to offer! Rick is super responsive, helpful, kind, and generous! Highly recommended, and hope to return soon :)
Places to stay in Chicago

Cute, Clean, Cozy Apartment in Pilsen
I was very impressed and pleased with all of the thoughtful details and extras like Keurig pods, filtered water and parking stickers. The space was cozy and perfect for our small family. It had every possible amenity needed to make ourselves at home for a week and cooking was a breeze. The location was ideal both due to the proximity to our daughter’s place, but also very quiet and walkable to everything you need including restaurants, stores, light rail and bus lines. Leigh-Anne was super responsive and flexible. The only word of caution would be that guests who are very tall (like over 6’) might find the ceilings too low, though they were perfect for us. We would definitely stay here again on a future trip.

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Polk Street Coach House Apartment, Little Italy/Medical Dist
the airbnb was so lovely and spacious for our party of 4! we had 0 trouble finding the home and had the best weekend in chicago reuniting with our friends from college. would def recommend - it is a quieter part of chicago. the walk to little italy is quite lovely and is a quick uber from the west loop

Explore Lincoln Park from a Polished Apartment
There is no way I/we can do a review of Elizabeth's beautiful apartment in just 1,000 characters. Met Elizabeth personally, made a wonderful connection. It's the most awesome airbnb we've ever stayed at. The apartment has been beautifully remodeled. As a retired general contractor, I was very impressed. The neighborhood is fantastic; great for walking, shopping, and there are restaurants galore. The location is fantastic for touring Chicago. The neighborhood is beautiful with lovely architecture and interesting shops. There are lots of families; couples walking, biking, babies-buggying. We enjoyed walking around the neighborhood after a walk to dinner or lunch. The bed/bedding is very comfortable and we slept very well. Great temp control, lots of windows, and a 65"flat screen TV. The bathroom is large and airy with a walk-in shower. The unit is very quiet, with dual-pane windows and black-out shades for sleeping in late. Stay here for the best Chicago experience.

Eddy Street Upstairs Apartment
Joe was awesome at communicating and hosting. He even allowed us to bring our reactive dog and we didn’t even have one bad interaction. It was awesome and I appreciate it. It will get warm during the summer time but that’s okay with us. We were happy to just bring our furbabies with us 💕

Private Logan Square Studio
very private and fit the description exactly!

Berwyn Musical Apartment
We stayed here for 2-weeks and it was perfect for our family of three. All of the amenities were as described and the washer/dryer proved extremely helpful during out time here. The location can't be beat, there's so much to do! It is very walkable to local bars, restaurants and parks. Train access is also a huge plus. We look forward to staying here again soon. Berwyn forever!

Pilsen Modernist, Creative, Lightfilled Loft
Really nice stay in Chicago. Very quiet and safe neighborhood. Daniel is very friendly to reach out. We’d choose to stay here again next time visiting Chicago.
Dog friendly houses in Chicago

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Staying at Matt’s Air BnB was a fantastic experience. We stayed with our two kids and another couple and the space was perfect for our group. The spacious, fenced in yard made for a great hangout space for our toddler to safely run around. The house looks exactly like the pictures and was extremely clean. We will definitely stay here again! Thank you, Matt!

Private 3rd Floor Apartment
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

BoHo House - A Chic, 1903 Chicago Workers Cottage
Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

Victorian House in Heart of Rogers Park
We had an excellent stay here. hosts went above and beyond to make sure we had everything we needed. beautiful house and parking spot was ideal.

Dog Friendly Cozy North Naperville 3 BED/2 BA Home
Nice place tucked into a quiet, safe neighborhood. Backyard was outstanding. (We wish the weather had cooperated so we could have spent more time outside) One level home with comfy beds and furniture throughout. Kitchen was spacious and clean. Plenty of extra towels and blankets.

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14
The house is very beautiful. My family and I loved the place and how spacious it is.

Quiet cul-de-sac with huge fenced in backyard
Tom's place was really nice and exactly as described. The backyard was perfect for our pup and the neighborhood was really nice to take him on the walk. We would defintely stay there again if we are in the area.

The Grand Kimball Lodge, Logan Square, Sleeps 14
Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!
Quick stats about vacation rentals in Chicago
Total rentals
11K properties
Total number of reviews
542K reviews
Family-friendly rentals
5.2K properties are a good fit for families
Pet-friendly rentals
3.6K properties allow pets
Rentals with a pool
1.2K properties have a pool
Rentals with dedicated workspaces
6.9K properties have a dedicated workspace
Your guide to Chicago
All About Chicago
Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.
You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.
The best time to stay in a vacation rental in Chicago
Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.
Top things to do in Chicago
The Art Institute of Chicago
The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.
Willis Tower
The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.
Millennium Park
Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.
Frequently Asked Questions
How is the weather in Chicago?
Chicago experiences a wide range of weather, from hot summers that can reach 95°F (35°C) to chilly winters that can drop to 20°F (-6°C). The city exhibits four distinct seasons, with beautiful spring blossoms, sunny summers, colorful autumns, and snow-dusted winters, perfect for ice skating in Millennium Park.
What are some of the best things to do in Chicago?
In Chicago, you can explore iconic sights like Navy Pier, Cloud Gate in Millennium Park, and Willis Tower's SkyDeck for breathtaking city views. Cultural enthusiasts can immerse themselves in the Art Institute of Chicago or catch an engaging show at the Second City comedy club.
What is the best time of year to visit Chicago?
Summer, from June to August, is often recommended to visit Chicago. During this season, the city hosts various events, including the Chicago Blues Festival and Taste of Chicago, attracting food and music enthusiasts alike. However, the city is vibrant year-round, with winter activities such as ice skating and holiday markets.
What are the best places to stay in Chicago?
Popular areas to stay in Chicago include the vibrant neighborhoods of River North and Gold Coast for their proximity to dining and shopping. Lincoln Park and Lakeview are also often recommended for their leafy streets, local cafes, and proximity to the lake.
What are the best places to visit in Chicago?
Popular places to visit in Chicago include the culturally rich neighborhoods like Chinatown, Little Italy, and Pilsen. Navy Pier, the Magnificent Mile shopping district, as well as green spaces like Grant Park and Lincoln Park, are also frequently suggested.
What are some hiking trails in Chicago?
While Chicago is an urban city, it still has some scenic hiking trails. The Chicago Lakefront Trail, a 18-mile (29 km) path along Lake Michigan, and the North Branch Trail System in the Forest Preserves of Cook County are popular among outdoor enthusiasts.
What are some family activities to do in Chicago?
Families often enjoy exploring the Shedd Aquarium, the Field Museum of Natural History, and the interactive exhibits at the Chicago Children's Museum. A boat tour along the Chicago River, highlighting the city's architectural marvels, is another frequently suggested activity for families.
What are some of the best day trip ideas in Chicago?
For day trips from Chicago, consider a visit to the Indiana Dunes National Park for some beach fun and hiking, or explore the charming town of Geneva for a relaxed pace with boutique shopping. Rockford, with its Anderson Japanese Gardens and Burpee Museum of Natural History, is also a viable option.
How much does it cost to stay in boutique hotel rentals in Chicago?
Experience the best of Chicago with our boutique hotel rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there boutique hotel rentals with a dedicated workspace in Chicago?
Yes! Work meets play with ease at over 30 boutique hotel rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park
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