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Vacation rentals in Chicago

Browse 5,524 available vacation homes and compared across 10 trusted partners
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Top 15 most Recommended Vacation Rentals in Chicago

Discover your ideal Chicago vacation rental with real-time comparisons of 5,524 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

B&B with patio, jacuzzi & yard

Sheffield & DePaul, Chicago, Illinois, United States
from $247
per night
Good
from $247
per night
View deal
Bed and breakfast Canaryville
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B | Good for workation

Canaryville, Chicago, Illinois, United States
from $55
per night
from $55
per night
View deal
Motel River North
Motel ∙ 5 guests ∙ 1 bedroom

Motel | Near Magnificent Mile

River North, Chicago, Illinois, United States
from $93
per night
Excellent
from $93
per night
View deal
Resort Bucktown
Resort ∙ 4 guests ∙ 1 bedroom

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

Bucktown, Chicago, Illinois, United States
from $335
per night
Excellent
from $335
per night
View deal
Bed and breakfast Canaryville
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast | Suitable for remote work

Canaryville, Chicago, Illinois, United States
from $55
per night
from $55
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 $87
per night
Outstanding
from $87
per night
View deal
Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace & yard | Good for workation

West Woodlawn, Chicago, Illinois, United States
from $87
per night
from $87
per night
View deal
Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

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

Bucktown, Chicago, Illinois, United States
from $190
per night
Outstanding(341 ratings)
from $190
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 $87
per night
Outstanding
from $87
per night
View deal
Bed and breakfast North Center
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with 1 room for 2 persons

North Center, Chicago, Illinois, United States
from $307
per night
from $307
per night
View deal
Bed and breakfast Rogers Park
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Nice bed and breakfast for 4 persons

Rogers Park, Chicago, Illinois, United States
from $80
per night
from $80
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 $156
per night
from $156
per night
View deal
Bed and breakfast Bucktown
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed and breakfast with garden & terrace | Good for workation

Bucktown, Chicago, Illinois, United States
from $189
per night
Outstanding(341 ratings)
from $189
per night
View deal
Bed and breakfast Logan Square
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Bed & breakfast with yard & terrace

Logan Square, Chicago, Illinois, United States
from $135
per night
from $135
per night
View deal
Bed and breakfast Andersonville
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

Andersonville, Chicago, Illinois, United States
from $67
per night
Good
from $67
per night
View deal

Vacation Rentals With Fireplaces

Bed and breakfast  Sheffield Neighbors
from $240
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
Fireplace
View deal
Bed and breakfast  Sheffield Neighbors
from $335
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
Fireplace
View deal
Bed and breakfast  Old Town
from $188
per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed & breakfast with patio

4.9
Outstanding(444 ratings)
Old Town, Chicago, Illinois, United States
Fireplace
View deal
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Vacation houses with Balconies or Patios

Resort  Bucktown
from $317
per night
Resort ∙ 2 guests ∙ 1 bedroom

Pleasant resort with sauna, heated pool & patio

Bucktown, Chicago, Illinois, United States
Balcony/Patio
View deal
Bed and breakfast  East Village
from $2,772
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
View deal
Bed and breakfast  Magnolia Glen
from $154
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with yard & patio

Magnolia Glen, Chicago, Illinois, United States
Balcony/Patio
View deal
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Vacation rentals and apartments with air conditioning

Bed and breakfast  West Loop
from $206
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant B&B for 2 persons

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
Air conditioning
View deal
Bed and breakfast  Bridgeport
from $302
per night
Bed and breakfast ∙ 9 guests ∙ 3 bedrooms

Wonderful bed and breakfast | Good for workation

5.0
Outstanding
Bridgeport, Chicago, Illinois, United States
Air conditioning
View deal
Bed and breakfast  West Loop
from $234
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
Air conditioning
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Chicago offering exceptional value for money

Bed and breakfast Bucktown
from $189
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with terrace & garden

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast Bucktown
from $195
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 Bucktown
from $185
per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Beautiful bed & breakfast with garden, grill & terrace | Pets are welcome

Bucktown, Chicago, Illinois, United States
View deal

Top-Rated Vacation rentals in Chicago

Book the highest-rated Chicago vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Bed and breakfast West Loop
from $267
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
Bed and breakfast Wicker Park
from $254
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with yard

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
View deal
Bed and breakfast West Loop
from $314
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant bed and breakfast for 2 persons

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

Discover real guest reviews to help you choose the perfect stay in Chicago

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 $77
per night
Hotel ∙ 2 guests ∙ 1 bedroom
4.5
Excellent(44 ratings)
River West, Chicago, Illinois, United States
View deal

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Verified reviews

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Spend your budget exactly as planned by comparing thousands of providers.

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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 Features & Amenities in Chicago

  • WiFi (5,447)
  • Pool (1,765)
  • Parking (1,376)
  • Pet-friendly (2,330)
  • Kitchen (963)
  • TV (4,962)
  • Air conditioning (5,288)
  • Balcony/patio (1,600)
  • Washing machine (1,622)
  • Microwave (1,845)
  • Fireplace (858)
  • No smoking (5,433)

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 4, 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 5,524 rentals
🌙 Nightly prices starting at $55
⭐ Popular amenities Internet, Pool and Parking
🐾 Pet friendly homes 2,308 homes
🏊 Vacation rentals with pools 1,764 homes
9 reviews
Chicago vacation rentals have an average rating of 4.3/5 on 9 reviews left by travelers.

Frequently Asked Questions

What is the nightly price for a vacation rental in Chicago?

Prices for vacation rentals in Chicago start from $55 per night. Average prices for bed and breakfast rentals are $437 per night. Apartment rentals in Chicago cost $280 per night on average.

How many vacation rentals are available to book in Chicago?

There are 5,524 vacation homes in Chicago to browse and book for your trip.

What are the most popular amenities for vacation rentals in Chicago?

The most popular amenities for vacation rentals in Chicago include accommodations with: Pool, Internet, and Parking.

How many vacation rentals with a pool are there in Chicago?

Chicago offers 1,764 Hotel room and Aparthotel available for booking.

Are pets allowed in vacation rentals in Chicago?

In case if you are traveling with a pet in Chicago - 42% of vacation rentals allow pets.

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