
Houses in Chicago
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Top-rated boutique hotel rooms in Chicago
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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 Iâll enhance it with more detail, warmth, or whatever tone youâre 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 didnât have to be on public transit for more than a half hour for anything we couldnât 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 daughterâs 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 6â) might find the ceilings too low, though they were perfect for us. We would definitely stay here again on a future trip.

Costa Lota Near Wrigley Field
I absolutely loved this place. It was very comfortable and I appreciated all the little design touches. I loved the seperate entrace from the rest of the building. It was a very Chicago apartment. I felt right at home. The water pressure was great and appreciated having a sound machine in the bedroom. Special shout out to the character drinking glasses. The location was perfect right off Ashland and close to Clark. I would love to stay here again sometime.

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.

Entire place with free parking.
Jose was awesome and the place was perfect! I would 100% stay here again. No concerns for parking, safe area, close to what I needed. Would recommend to anyone considering this place!

The Grotto of Logan Square
Benjamin's place fit my needs exactly: super comfortable bed, clean bathroom, lots of surfaces for keeping stuff organized. Benjamin was super responsive upon check-in which is so helpful. I will definitely be staying there again!

Elegant Suite in Gold Coast
A perfect stay! Next time I am in Chicago, this will be my first choice. I "second" all the great things that everyone else has said. I was here for a multi-day conference at a very nearby hotel, and I am so glad I chose here over the host hotel. Wonderful staff, great communication! Top notch in every respect! Thank you!

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

Berwyn Musical Apartment
Had a great experience, Kara the host was extremely kind and responsive with my questions and the place listed was exactly as it looked.Overall had a great stay!
Dog friendly houses in Chicago

MiniGolfHouse-Chicago Close Beach & Indoor Fun!
This wasnât really supposed to be a âfunâ trip. I unfortunately had to put my mom into assisted living, but found this Airbnb close to her home. My 2 boys came with me (10 & 13) and if it wasnât for the fun accommodations in this house, they wouldnât have had the awesome time they did. It was a fantastic distraction, and the house felt like a home. We loved the updated bathrooms, the modern look and feel, and donât forget the basement! We spent lots of time down there playing putt putt and arcade games. My son even hooked up his X-Box and played (which he ended up leaving behind on accident, and the host Marc actually drove it to my moms to drop it off - A SAINT!) We will likely be back at least every couple months to check on my mom and will book here from now on!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Staying at Mattâs 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 itâs 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 theyâre fairly steep and small, so if you have mobility issues that would be a concern. I donât 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 itâs a great place to explore and hang out.

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!

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.

Retro Modern Bungalow | fire pit | free parking
This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!

The Sunshine Spot
House is centrally located . Clean. Host was responsive. 100% recommend this property !

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.
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, thereâs a unique aura found in each.
Youâll 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
Chicagoâs 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 itâs 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 thereâs 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 cityâs 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 thatâs 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. Itâs 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 âThe Bean.â 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.
Destinations to explore
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- Cabins United States
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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
- Flossmoor Golf Club
- Things to do Chicago
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- Family travel hub Tips and inspiration
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- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes