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Chicago Vacation Rentals

Find 5,520 available home rentals from 10 partners
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Top 15 Recommended vacation rentals in Chicago

Find your perfect vacation rental in Chicago from just $86 per night!

Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Euro Room

Sheffield Neighbors, Chicago, Illinois, United States
This cozy bed and breakfast in Sheffield Neighbors offers beach access, a fireplace, and a balcony for a perfect getaway.
from $334
per night
Excellent(99 ratings)
from $334
per night
View deal
Bed and breakfast West Loop
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Meno)

West Loop, Chicago, Illinois, United States
This West Loop bed and breakfast features a cozy setting for two, with free breakfast and an ideal backdrop for weddings.
from $303
per night
Outstanding(166 ratings)
from $303
per night
View deal
Bed and breakfast West Loop
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Carmen)

West Loop, Chicago, Illinois, United States
This intimate West Loop bed and breakfast offers a free breakfast and is perfect for a romantic getaway or a wedding celebration.
from $394
per night
Outstanding(166 ratings)
from $394
per night
View deal
Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Capone's Cantina

Sheffield Neighbors, Chicago, Illinois, United States
This bed and breakfast in Sheffield Neighbors offers beach access, a balcony, and a cozy fireplace for unforgettable getaways.
from $408
per night
Excellent(99 ratings)
from $408
per night
View deal
Bed and breakfast Boystown
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

Five bedroom - 3 bath - Sleeps 12

Boystown, Chicago, Illinois, United States
This inviting bed and breakfast in Boystown offers a kitchen, balcony, free breakfast, and parking for up to 12 guests.
from $918
per night
from $918
per night
View deal
Bed and breakfast Bucktown
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Cardinal Room (First Floor)

Bucktown, Chicago, Illinois, United States
This Bucktown bed and breakfast features a kitchen, spa, and yard, providing a perfect retreat for you and your pet.
from $263
per night
Outstanding(341 ratings)
from $263
per night
View deal
Bed and breakfast West Loop
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Harvey)

West Loop, Chicago, Illinois, United States
This West Loop bed and breakfast offers a perfect setting for two, complete with free breakfast and an ideal backdrop for weddings.
from $389
per night
Outstanding(166 ratings)
from $389
per night
View deal
Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room with a View (Second Floor)

Bucktown, Chicago, Illinois, United States
This Bucktown bed and breakfast features a kitchen, spa, and yard, perfect for a relaxing getaway with your pet.
from $263
per night
Outstanding(341 ratings)
from $263
per night
View deal
Bed and breakfast West Loop
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Bellow)

West Loop, Chicago, Illinois, United States
This West Loop bed and breakfast offers a cozy retreat for two, complete with free breakfast and a perfect wedding venue.
from $342
per night
Outstanding(166 ratings)
from $342
per night
View deal
Bed and breakfast West Loop
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Suite, 1 King Bed (Sinclair)

West Loop, Chicago, Illinois, United States
A cozy bed and breakfast in West Loop, perfect for a romantic getaway or an unforgettable wedding celebration for two.
from $454
per night
Outstanding(166 ratings)
from $454
per night
View deal
Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Grand Tuscan Suite

Sheffield Neighbors, Chicago, Illinois, United States
This inviting bed and breakfast in Sheffield Neighbors features beach access, a cozy fireplace, and a balcony for unforgettable stays.
from $471
per night
Excellent(99 ratings)
from $471
per night
View deal
Bed and breakfast Bucktown
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

DaVinci Room (Second Floor)

Bucktown, Chicago, Illinois, United States
This pet-friendly bed and breakfast in Bucktown features a spa, kitchen, yard, free breakfast, and parking for an unforgettable getaway.
from $271
per night
Outstanding(341 ratings)
from $271
per night
View deal
Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Chickadee room (First Floor)

Bucktown, Chicago, Illinois, United States
This Bucktown bed and breakfast features a kitchen, spa, and yard, perfect for a relaxing getaway with your pet.
from $271
per night
Outstanding(341 ratings)
from $271
per night
View deal
Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Venetian Suite

Sheffield Neighbors, Chicago, Illinois, United States
This bed and breakfast in Sheffield Neighbors offers beach access, a cozy fireplace, and a yard perfect for weddings.
from $337
per night
Excellent(99 ratings)
from $337
per night
View deal
Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Woodpecker (Second Floor)

Bucktown, Chicago, Illinois, United States
This Bucktown bed and breakfast features a kitchen, spa, free breakfast, and a yard, perfect for a cozy getaway with your pet.
from $255
per night
Outstanding(341 ratings)
from $255
per night
View deal

Vacation rentals with a fireplace

Motel  Archer Heights
from $114 per night
Motel ∙ 10 guests ∙ 1 bedroom

Motel

Archer Heights, Chicago, Illinois, United States
Fireplace
View deal
Bed and breakfast  Old Town
from $253 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Deluxe Suite, 1 King Bed

4.9
Outstanding(444 ratings)
Old Town, Chicago, Illinois, United States
Fireplace
View deal
Motel  Archer Heights
from $180 per night
Motel ∙ 4 guests ∙ 1 bedroom

Traditional Room, 2 Queen Beds, Non Smoking

3.2
(970 ratings)
Archer Heights, Chicago, Illinois, United States
Fireplace
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Vacation rentals and apartments with air conditioning

Bed and breakfast  Sheffield Neighbors
from $408 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Florencia Suite

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
Air conditioning
View deal
Bed and breakfast  Wicker Park
from $360 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Concord)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
Air conditioning
View deal
Bed and breakfast  Wicker Park
from $418 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Exclusive Apartment, 1 Queen Bed with Sofa bed (Garden)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
Air conditioning
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Apartments with a balcony or patio

Bed and breakfast  Bucktown
from $263 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Skylight Room (Upstairs)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
Balcony/Patio
View deal
Bed and breakfast  Bucktown
from $271 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Egret Room (Second Floor)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
Balcony/Patio
View deal
Resort  Bucktown
from $389 per night
Resort ∙ 10 guests ∙ 1 bedroom

Resort

Bucktown, Chicago, Illinois, United States
Balcony/Patio
View deal
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Budget-friendly Rentals in Chicago

Find Fantastic yet Inexpensive Rentals

Bed and breakfast Wicker Park
from $334 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Wabansia)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from $384 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Hoyne)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from $384 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Wolcott)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
View deal

Top-Rated Offers and Accommodations in Chicago

Book Vacation Rentals with the Highest User Rating

Bed and breakfast Bucktown
from $271 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Eagles Nest (Second Floor)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast Magnolia Glen
from $222 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Premier Room (Room 1)

4.5
Excellent(472 ratings)
Magnolia Glen, Chicago, Illinois, United States
View deal
Bed and breakfast Magnolia Glen
from $240 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Premium Room (Room 3)

4.5
Excellent(472 ratings)
Magnolia Glen, 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 $107 per night
Hotel ∙ 2 guests ∙ 1 bedroom
4.5
Excellent(44 ratings)
River West, Chicago, Illinois, United States
View deal

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

Popular Rental Amenities in Chicago

  • WiFi (5,451)
  • Pool (1,738)
  • Kitchen (959)
  • TV (4,973)
  • Air conditioning (5,288)
  • Parking (1,373)
  • Washing machine (1,621)
  • Pet-friendly (2,332)
  • Balcony/patio (1,600)
  • Microwave (1,850)
  • Dishwasher (462)
  • No smoking (5,435)

Chicago is a wonderful vacation spot if you want an accommodation with a pool, as 32% of the vacation rentals there have one. Interestingly, our data shows that more hotel room have a pool than aparthotel. Additionally, they can welcome 4 vacationers, on average, while aparthotel with pools can host an average of 4 people. two-thirds of Chicago's vacation homes including a pool are located within two kilometres of water, choose between some pool time or waterfront moments.

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?

Special Tips for Activities with Children

There's no shortage of options to entertain your family if you're visiting Chicago with kids who love animals. Shedd Aquarium is both exciting and educational for kids, with fun interactive displays, live shows, play zones, and exhibits on marine life around the world. Brookfield Zoo is a vast, 216-acre nature park in Chicagoland that's home to hundreds of different animals, a fun motor safari tram, a huge butterfly world, and the Family Play Zoo where you can dress up as zookeepers or furry friends. Closer to downtown, historic Lincoln Park Zoo has exotic creatures like red pandas, snow monkeys, leopards, a classic carousel, and other fun rides.

A ride for kids of all ages is the Navy Pier's Centennial Wheel, which gives fantastic city views topped only by heading up to 360 Chicago on the 94th floor of the John Hancock Tower on Michigan Avenue. For a different perspective of Chicago, hop on board the Tall Ship Windy at Navy Pier and enjoy great city views from Lake Michigan aboard an authentic 4-mast schooner. Kids can even join in and hoist the sails themselves!

The world-class Chicago Children's Museum has hands-on, interactive displays and exhibits, including the popular ""Dinosaur Expedition"" where kids can join an archaeological dig and explore a real fossil pit. The Adler Planetarium lets kids have the feeling of going to outer space without even leaving Chicago, and LEGOLAND Chicago is a toy wonderland with life-sized LEGO displays, interactive areas, and a 4D theatre.

What are the top sights in Chicago?

Things to Do and See

The city's most popular attraction is the Lincoln Park Zoo, which houses African apes and other interesting species. Trivia lovers will be impressed to learn that Chicago is home to three out of America's five tallest buildings: the Sears Tower, Trump Tower, and the Aon Center.

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.

What are the must-see attractions in Chicago?

Chicago: Culture in the Windy City

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.

Museum of Science and Industry

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

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.

Millennium Park

This 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.

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, ancient sculptures, and more feature.

Information about vacation rentals in Chicago

🏡 Vacation rentals available 5,478 rentals
🌙 Nightly prices starting at $86
⭐ Popular amenities Internet, Pool and Kitchen
🐾 Pet friendly homes 2,329 homes
🏊 Vacation rentals with pools 1,737 homes
7 reviews
Chicago vacation rentals have an average rating of 4.1/5 on 7 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Chicago?

At the moment, there are 5,478 vacation homes from 10 different providers in Chicago.

What are the most popular vacation home amenities in Chicago?

Many travellers are searching for Internet, Pool, and Kitchen when booking a vacation home in Chicago.

Are there pet-friendly vacation rentals in Chicago?

If you're travelling with a dog, over 43% of vacation rentals in Chicago are pet-friendly.

What's the best month to visit Chicago?

When booking a vacation rental in Chicago, remember that the rainiest months are usually March and April, with February often being the sunniest.

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