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Vacation Rentals in Chicago

Find 10,997 available offers from 24 partners
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1 guest
Anytime
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Recommended vacation rentals in Chicago

Find your perfect vacation rental in Chicago from just $59 per night!

Villa South Shore
Jan 12 - Jan 19
Villa ∙ 16 guests ∙ 3 bedrooms

Villa with 3 Rooms for 16 Persons

South Shore, Chicago, Illinois, United States
$326
per night
$326
per night
View deal
Condo Lincoln Park
Feb 8 - Feb 15
Condo ∙ 7 guests ∙ 4 bedrooms

Family-Oriented Condo with Patio & Yard

Lincoln Park, Chicago, Illinois, United States
$172
per night
Outstanding(35 ratings)
$172
per night
View deal
House Goose Island
Mar 2 - Mar 9
House ∙ 14 guests ∙ 3 bedrooms

Family-Friendly Big House with Barbeque, Terrace & Sauna | City View | Perfect for Remote Work

Goose Island, Chicago, Illinois, United States
$228
per night
Outstanding(51 ratings)
$228
per night
View deal
House Douglas
-19%
Aug 9 - Aug 16
House ∙ 9 guests ∙ 4 bedrooms

House with Patio

Douglas, Chicago, Illinois, United States
$384$109
per night
Very good(28 ratings)
$384$109
per night
View deal
Apartment South Loop
-73%
Feb 8 - Feb 15
Apartment ∙ 8 guests ∙ 3 bedrooms

Family-Friendly Nice Rental Apartment with Pool, Terrace & Grill | Perfect for Remote Work

South Loop, Chicago, Illinois, United States
$1,042$300
per night
Outstanding(60 ratings)
$1,042$300
per night
View deal
Apartment Near North Side
Jul 5 - Jul 12
Apartment ∙ 10 guests ∙ 2 bedrooms

Fully Equipped Holiday Apartment | City View | Perfect for Remote Work

Near North Side, Chicago, Illinois, United States
$487
per night
Outstanding(9 ratings)
$487
per night
View deal
Apartment Roscoe Village
-63%
Feb 8 - Feb 15
Free cancellation
Apartment ∙ 10 guests ∙ 1 bedroom

Beautiful Rental Apartment with Yard

Roscoe Village, Chicago, Illinois, United States
$329$135
per night
Very good
$329$135
per night
View deal
Apartment Rush & Division
-76%
Feb 4 - Feb 11
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-Friendly Rental Apartment with Terrace | Near John Hancock Center | City View | Pets Are Welcome

Rush & Division, Chicago, Illinois, United States
$1,044$1,119
per night
Outstanding(4 ratings)
$1,044$1,119
per night
View deal
Apartment Streeterville
-66%
Feb 8 - Feb 15
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental Apartment with Terrace | Near John Hancock Center | City View | Perfect for Remote Work

Streeterville, Chicago, Illinois, United States
$600$183
per night
Outstanding(36 ratings)
$600$183
per night
View deal
Apartment Heart of Chicago
-38%
Jul 5 - Jul 12
Apartment ∙ 6 guests ∙ 4 bedrooms

Fully Equipped Beautiful Holiday Apartment with Terrace | City View | Perfect for Remote Work

Heart of Chicago, Chicago, Illinois, United States
$743$226
per night
Outstanding(7 ratings)
$743$226
per night
View deal
House Streeterville
Jul 5 - Jul 12
House ∙ 12 guests ∙ 3 bedrooms

Charming House | Close to John Hancock Center | City View | Pets Are Welcome

Streeterville, Chicago, Illinois, United States
$263
per night
$263
per night
View deal
House Bridgeport
Feb 4 - Feb 11
House ∙ 12 guests ∙ 4 bedrooms

Children-Friendly House with Garden & Terrace | Perfect for Remote Work | Pet-Friendly

Bridgeport, Chicago, Illinois, United States
$268
per night
Outstanding(23 ratings)
$268
per night
View deal
House West Town
Feb 8 - Feb 15
House ∙ 13 guests ∙ 5 bedrooms

Fully Equipped House with BBQ

West Town, Chicago, Illinois, United States
$272
per night
Very good(15 ratings)
$272
per night
View deal
House West Town
Feb 4 - Feb 11
House ∙ 10 guests ∙ 5 bedrooms

House with BBQ

West Town, Chicago, Illinois, United States
$430
per night
$430
per night
View deal
House Grand Boulevard
Feb 8 - Feb 15
House ∙ 8 guests ∙ 3 bedrooms

House with 3 Rooms for 8 Persons

Grand Boulevard, Chicago, Illinois, United States
$273
per night
Outstanding(2 ratings)
$273
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Old Town Triangle
Jul 20 - Jul 27
$163
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with 2 Rooms for 4 Persons

4.4
Very good(34 ratings)
Old Town Triangle, Chicago, Illinois, United States
Air conditioning
View deal
Apartment  Near North Side
Jul 20 - Jul 27
$546
per night
Apartment ∙ 11 guests ∙ 3 bedrooms

Fully Equipped Apartment with Patio | City View

4.3
Very good(35 ratings)
Near North Side, Chicago, Illinois, United States
Air conditioning
View deal
Apartment  Streeterville
Jul 20 - Jul 27
$725
per night
Apartment ∙ 6 guests ∙ 4 bedrooms

Rental Apartment with Terrace | Close to John Hancock Center | City View

4.8
Outstanding(25 ratings)
Streeterville, Chicago, Illinois, United States
Air conditioning
View deal
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Best Vacation Home Deals in Chicago

Save up to 76%

Condo Old Town Triangle
Jan 21 - Jan 28
-76%
$539
$127
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with 2 Rooms for 4 Persons

4.4
Very good(35 ratings)
Old Town Triangle, Chicago, Illinois, United States
View deal
House Edgewater Beach
Jan 21 - Jan 28
-58%
$511
$214
per night
House ∙ 12 guests ∙ 6 bedrooms

Family-Friendly Vacation Home with Barbeque & Terrace | Good for Workation | Dogs Allowed

5.0
Outstanding(2 ratings)
Edgewater Beach, Chicago, Illinois, United States
View deal
Apartment Streeterville
Feb 7 - Feb 14
-67%
$763
$253
per night
Apartment ∙ 6 guests ∙ 4 bedrooms

Rental Apartment with Terrace | Close to John Hancock Center | City View

4.7
Excellent(27 ratings)
Streeterville, Chicago, Illinois, United States
View deal

Discover a vacation rental fitting your needs among the 10,997 beautiful properties from more than 24 partner websites in Chicago. Using HomeToGo you can instantly search and compare the offers of each listed rental to find the best price and save up to 81%.

Budget-friendly Vacation Rentals in Chicago

Find Fantastic yet Inexpensive Offers

Apartment Fulton River District
Jul 12 - Jul 19
$756
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Ample Rental Apartment with Grill & Terrace | City View | Suitable for Remote Work

4.8
Outstanding(14 ratings)
Fulton River District, Chicago, Illinois, United States
View deal
House Goose Island
Mar 2 - Mar 9
-64%
$429
$169
per night
House ∙ 9 guests ∙ 2 bedrooms

Fully Equipped House with Terrace | City View

4.0
Very good(3 ratings)
Goose Island, Chicago, Illinois, United States
View deal
House Old Town
Feb 8 - Feb 15
$1,035
per night
House ∙ 12 guests ∙ 7 bedrooms

House with Sauna, Yard & Patio | City View

5.0
Outstanding(68 ratings)
Old Town, Chicago, Illinois, United States
View deal

Top-Rated Rentals and Accommodations in Chicago

Book Vacation Rental Offers with the Highest User Rating

Condo Lake View East
Jan 6 - Jan 13
$472
per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with 3 Rooms for 7 Persons

4.7
Excellent(26 ratings)
Lake View East, Chicago, Illinois, United States
View deal
Apartment Near North
Jul 5 - Jul 12
$247
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday Apartment with Terrace | Close to John Hancock Center | City View

4.9
Outstanding(7 ratings)
Near North, Chicago, Illinois, United States
View deal
Apartment Logan Square
Jan 6 - Jan 13
$136
per night
Apartment ∙ 4 guests ∙ 3 bedrooms

Wonderful Holiday Apartment | Pet-Friendly

5.0
Outstanding(5 ratings)
Logan Square, Chicago, Illinois, United States
View deal

Customer ratings and reviews

How are reviews collected?
Abdullah N.
Guest verified by HomeToGo

I will definitely rent it out next time, best place to get if you want to visit chicago. 25-30 mins away from Downtown Chicago. Luxury and got so much Room for kids to play around. You can get 12/13 beds easily.

Reviewed on 12/2/2024 | Family
Apartment South Austin
from $334
per night
HomeToGo
Apartment ∙ 12 guests ∙ 4 bedrooms
4.7
Excellent(3 ratings)
South Austin, Chicago, Illinois, United States
View deal
from $334
per night
Apartment ∙ 12 guests ∙ 4 bedrooms
4.7
Excellent(3 ratings)
South Austin, Chicago, Illinois, United States
HomeToGo
View deal

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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 Rental Amenities in Chicago

  • WiFi (10,366)
  • Pool (2,507)
  • Parking (1,711)
  • Pet-friendly (4,662)
  • Kitchen (6,139)
  • TV (9,679)
  • Air conditioning (10,476)
  • Balcony/patio (2,585)
  • Washing machine (5,546)
  • Microwave (5,736)
  • Hot tub (339)
  • Fireplace (1,496)

Nearly a quarter of the accommodations provide a pool, which makes Chicago a wonderful destination for vacationers looking to relax pool-side. In addition, more Apartment rental have pools than any other type of property. They are an excellent choice if you go in a group of 7, as that is the number of people they can welcome on average. If you would ideally like to be close to the water, many of the vacation rentals with a pool are located within 2 miles of the waterfront.

Price and Availability Index in Chicago

Click on any bar to see price and availability information

Vacation Rental Price Information in Chicago

We analyzed price data and input them into this graph, which displays vacation rental prices for the next twelve months in Chicago. In October, prices go up to $732 per night (10/4 – 10/11), which is the most expensive time of the year to book a vacation home. Vacation rental prices go down to $131 per night in November (11/8 – 11/15).

Rental availability information in Chicago

Check out the graph above to learn about the percentage accommodations are available in Chicago throughout the year. It is harder to find an accommodation during a week of November (11/8 – 11/15), as 93% of the rentals are booked. It is easier to find a rental in a week of May (5/31 – 6/7), as only 33% of the accommodations are booked.

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 10,997 rentals
💳 Possible discounts up to 81%
🌙 Nightly prices starting at $59
⭐ Popular amenities Internet, Pool and Parking
🐾 Pet friendly homes 4,720 homes
🏊 Vacation rentals with pools 2,521 homes
5,811,261 reviews
Chicago vacation rentals have an average rating of 4.3/5 on 5,811,261 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 $59. Average prices for apartment rentals are $351 per night. House rentals in Chicago cost on average $535 per night.

How many vacation homes are available for booking in Chicago?

Currently there are 10,997 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 2,521 vacation rentals from 24 providers in Chicago.

Are pets allowed in vacation homes in Chicago?

If you are traveling with a dog in Chicago - 43% 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.

Find the perfect Chicago home to match your style

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