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Vacation rentals in Chicago

Find 5,415 available vacation homes from 12 partners
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Top 15 Recommended vacation rentals in Chicago

Find your perfect vacation rental in Chicago from just $44 per night!

Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with 1 room for 2 persons

West Woodlawn, Chicago, Illinois, United States
from $83
per night
from $83
per night
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Bed and breakfast Bronzeville
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Nice bed and breakfast with 1 room for 2 persons

Bronzeville, Chicago, Illinois, United States
from $102
per night
from $102
per night
View deal
Bed and breakfast Bridgeport
Bed and breakfast ∙ 9 guests ∙ 3 bedrooms

Wonderful bed and breakfast with 3 rooms for 9 persons

Bridgeport, Chicago, Illinois, United States
from $304
per night
Outstanding
from $304
per night
View deal
Bed and breakfast University Village / Little Italy
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

University Village / Little Italy, Chicago, Illinois, United States
from $231
per night
from $231
per night
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Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Nice bed & breakfast with terrace, barbeque & yard | Good for workation

Sheffield Neighbors, Chicago, Illinois, United States
from $242
per night
Excellent(99 ratings)
from $242
per night
View deal
Bed and breakfast Hyde Park
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with 1 room for 2 persons

Hyde Park, Chicago, Illinois, United States
from $146
per night
from $146
per night
View deal
Bed and breakfast Roscoe Village
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

Fully equipped pleasant bed and breakfast with yard & patio | Good for workation

Roscoe Village, Chicago, Illinois, United States
from $219
per night
Outstanding(158 ratings)
from $219
per night
View deal
Bed and breakfast Roscoe Village
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented charming B&B with patio & yard

Roscoe Village, Chicago, Illinois, United States
from $397
per night
Outstanding(105 ratings)
from $397
per night
View deal
Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with barbecue, patio & yard

West Woodlawn, Chicago, Illinois, United States
from $86
per night
Outstanding
from $86
per night
View deal
Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with patio & garden

West Woodlawn, Chicago, Illinois, United States
from $83
per night
from $83
per night
View deal
Bed and breakfast Englewood
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed & breakfast for 3 persons

Englewood, Chicago, Illinois, United States
from $66
per night
from $66
per night
View deal
Bed and breakfast West Ridge
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with 1 room for 2 persons

West Ridge, Chicago, Illinois, United States
from $152
per night
from $152
per night
View deal
Bed and breakfast South Austin
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with 1 room for 2 persons

South Austin, Chicago, Illinois, United States
from $133
per night
from $133
per night
View deal
Bed and breakfast Illinois Medical District
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming bed and breakfast for 2 persons

Illinois Medical District, Chicago, Illinois, United States
from $204
per night
from $204
per night
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Bed and breakfast Avondale
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

B&B for 4 persons

Avondale, Chicago, Illinois, United States
from $163
per night
from $163
per night
View deal

Vacation rentals and apartments with air conditioning

Bed and breakfast  Near West Side
from $222
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast for 2 persons

Near West Side, Chicago, Illinois, United States
Air conditioning
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Bed and breakfast  Illinois Medical District
from $142
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

Illinois Medical District, Chicago, Illinois, United States
Air conditioning
View deal
Bed and breakfast  Bucktown
from $233
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented wonderful bed and breakfast with terrace & garden | Suitable for remote work | Pets are welcome

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
Air conditioning
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Vacation houses with Balconies or Patios

Bed and breakfast  Magnolia Glen
from $180
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with yard & patio

Magnolia Glen, Chicago, Illinois, United States
Balcony/Patio
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Bed and breakfast  Douglas
from $187
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with yard & terrace | Perfect for remote work

Douglas, Chicago, Illinois, United States
Balcony/Patio
View deal
Bed and breakfast  East Village
from $4,604
per night
Bed and breakfast ∙ 16 guests ∙ 8 bedrooms

B&B with garden | Perfect for remote work

East Village, Chicago, Illinois, United States
Balcony/Patio
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Vacation homes and rentals with a yard

Bed and breakfast  Sheffield Neighbors
from $268
per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Lovely bed & breakfast with barbeque, patio & yard | Suitable for remote work

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
Yard
View deal
Bed and breakfast  Bucktown
from $245
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented spacious B&B with patio & yard | Good for workation | Pets allowed

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
Yard
View deal
Bed and breakfast  Sheffield Neighbors
from $242
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming B&B with grill, yard & patio | Perfect for remote work

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
Yard
View deal
See all offers

Budget-friendly Vacation Rentals in Chicago

Find Fantastic yet Inexpensive Offers

Bed and breakfast Woodlawn
from $134
per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Lovely bed & breakfast | Perfect for remote work

Woodlawn, Chicago, Illinois, United States
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Bed and breakfast Near West Side
from $142
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming B&B for 2 persons

Near West Side, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from $249
per night
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Wonderful bed and breakfast for 6 persons

4.8
Outstanding
Wicker Park, Chicago, Illinois, United States
View deal

Top-Rated Rentals and Accommodations in Chicago

Book Vacation Rental Offers with the Highest User Rating

Resort Bucktown
from $268
per night
Resort ∙ 127 guests ∙ 1 bedroom

Resort with terrace, sauna & hot tub | Suitable for remote work

4.5
Excellent
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast Bucktown
from $314
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with patio & garden

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast West Loop
from $339
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
View deal

Customer ratings and reviews

How are reviews collected?
Laura G.
Guest verified by HomeToGo

The room was clean, compact and perfect for travel. It was very close to the blue line, so transportation was easy.

Reviewed on 6/12/2025
Hotel River West
from $78
per night
HomeToGo
Hotel ∙ 2 guests ∙ 1 bedroom
4.5
Excellent(34 ratings)
River West, Chicago, Illinois, United States
View deal

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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Chicago

  • WiFi (5,280)
  • Pool (1,765)
  • Parking (1,379)
  • Pet-friendly (2,244)
  • Kitchen (987)
  • TV (4,837)
  • Air conditioning (5,302)
  • Balcony/patio (1,580)
  • Washing machine (1,582)
  • Microwave (1,765)
  • Hot tub (72)
  • Fireplace (872)

One-third of the accommodations provide a pool, which makes Chicago a wonderful destination for vacationers looking to relax pool-side. In addition, more Bed and breakfast rental have pools than any other type of property. They are an excellent choice if you go in a group of 8, as that is the number of people they can welcome on average. If you would ideally like to be close to the water, two-thirds of the vacation rentals with a pool are located within 2 miles of the waterfront.

Chicago Condo Rental: Enjoy a Fun and Cultural Trip

The historic city of Chicago boasts a fabulous skyline and a profusion of world-class museums, art galleries, jazz clubs, and playhouses. A walk through downtown Chicago will reveal some of the world's best architectural styles: Gothic, classic, modernist, and more.

The winds that blow across Lake Michigan have earned Chicago a nickname as the Windy City. Check in at your Chicago condo and find out what the fuss is all about.

What are the best activities for families in Chicago?

Activities with Children

Chicago has plenty to keep kids occupied. Right along the lake on Museum Campus lie three institutions within walking distance of each other. The Adler Planetarium has the coolest astronomy shows and exhibits, while the Shedd Aquarium features majestic sharks, dolphins, whales, and other superb marine life. The kids will love the giant Tyrannosaurus Rex skeleton in the Field Museum of Natural History. How about a picnic on the clean shores of Lake Michigan to finish up? The waters are safe and excellent for swimming.

What are the best places to discover the arts and culture of Chicago?

Art and Culture in the City

Art and history enthusiasts will have plenty of choice with the variety of art galleries and museums scattered across the city. The Art Institute of Chicago in the Loop district houses priceless Impressionist and Modernist works, and there's also the National Museum of Mexican Art in Pilsen, the Museum of Photography, the Polish Museum of America in Wicker Park, the International Museum of Surgical Science, and more. Buy the Chicago CityPASS to save money if you plan on visiting several attractions in a short span of time.

For improvisational comedy and performance art, catch a show at The Annoyance Theater, I.O., or the Playground. Steppenwolf in Lincoln Park is more serious, having hosted the likes of John Malkovich. Visit the Auditorium in the Loop for its architecture and brilliant use of performance space. For rock, blues, jazz, and spoken-word performances, the Chicago Theater awaits.

What are the top sights in Chicago?

The Best Neighborhoods in Chicago

Chicago's international neighborhoods are so true-to-life, you'd be forgiven for thinking you were genuinely in another country. There's Chinatown, the Korean community in Lawrence Avenue, the Swedish settlement at Andersonville, Little Italy, Greektown, and several other international pockets. The Polish Cathedrals of St. Mary of the Angels in Bucktown and St. Hyacinth Basilica in Avondale are exquisite. Experience the different facets of the city with guided architecture walks or a river boat tour.

The world comes to Chicago for gastronomical expertise, so indulge those taste buds! Devon Avenue is the place for Indian delights, and a mix of everything is served in Uptown, including American, Ghanaian, Nigerian, Japanese, and even Swedish delicacies.

Chicago is a drinking city that is home to a record number of dive bars, lounges, and breweries, the best of them found in the Logan Square and Bucktown areas.

Where are the unique attractions in Chicago?

3 Great Day Trips from Chicago

The city’s location makes it convenient to explore neighboring destinations on short day trips. Just a 90-minute drive will take you to Milwaukee, a city known for its breweries. The Milwaukee Public Museum, Discovery World, and Harley-Davidson Museum are popular attractions in this Wisconsin city.

Get more out of your stay at a Chicago vacation house with a trip to Starved Rock State Park. A delight for outdoor enthusiasts, this park is known for the many sandstone canyons that were created by glacial meltwater. Explore the different hiking trails through lush green areas and spend time by the waterfalls.

Another worthwhile trip is to Michigan City, just an hour away from Chicago. Spend the day visiting popular attractions like Washington Park, the Old Lighthouse Museum, and the gorgeous Barker Mansion. Family vacationers can visit the zoo and later hit the beach area for some boating, surfing, and swimming.

What are the must-see attractions in Chicago?

6 Must-See Attractions in Chicago

1. 360 Chicago Observation Deck

What better to way to see the city than from above? Travel up to the 94th floor of the John Hancock Center for stunning views of the city and over Lake Michigan.

2. Lincoln Park Zoo

The city's most popular attraction, this iconic zoo houses African apes and other interesting species. Be sure to allow for plenty of time to explore its plentiful and varied exhibits!

3. Museum of Science and Industry

At this world-class interactive museum, you'll find a life-size replica coal mine and recreated historic Chicago streets, with functional shops and other interesting querks.

4. Cloud Gate

One of the most iconic pieces of art in the United States, Cloud Gate was created by Anish Kapoor. This beautiful reflective sculpture is nicknamed 'The Bean' due to its shape, and attracts photographers from across the world.

5. Millennium Park

This majestic urban park in the center of Chicago is a great place to wile away an afternoon amidst a tranquil backdrop. Concerts, local fairs, and fun events are held regularly at the park.

6. Art Institute of Chicago

As one of the oldest and largest galleries in the country, this impressive museum showcases over 300,000 artworks. Modern art, photography, and ancient sculptures are all on display for visitors to enjoy.

Information about vacation rentals in Chicago

🏡 Vacation rentals available 5,476 rentals
🌙 Nightly prices starting at $65
⭐ Popular amenities Internet, Pool and Parking
🐾 Pet friendly homes 2,222 homes
🏊 Vacation rentals with pools 1,763 homes
10 reviews
Chicago vacation rentals have an average rating of 4.2/5 on 10 reviews left by travelers.

Frequently Asked Questions

What is the average price per night for a vacation home in Chicago?

The nightly price of accommodations in Chicago starts at $65. Average prices for bed and breakfast rentals are $495 per night. Apartment rentals in Chicago cost on average $280 per night.

How many vacation homes are available for booking in Chicago?

Currently there are 5,476 rentals in Chicago to browse and rent for your upcoming trip.

What amenities are most popular for vacation rentals in Chicago?

Usually travelers search for Pool, Internet, and Parking when booking a vacation rental in Chicago.

How many vacation homes with a pool are in Chicago?

There are 1,763 vacation rentals from 11 providers in Chicago.

Are pets allowed in vacation homes in Chicago?

If you are traveling with a dog in Chicago - 41% of vacation homes allow pets.

What's the best month to travel to Chicago?

If you are booking a vacation home in Chicago, consider that rainy season is typically in March or April, with February often being the driest.

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