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Vacation Rentals in Chicago

Find 11,235 available house rentals from 24 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Chicago

Find your perfect vacation rental in Chicago from just $80 per night!

House South Deering
Jun 28 - Jul 5
House ∙ 8 guests ∙ 4 bedrooms

House with garden | Suitable for remote work

South Deering, Chicago, Illinois, United States
$289
per night
Outstanding(1 rating)
$289
per night
View deal
Apartment Rush & Division
Sep 19 - Sep 26
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-friendly rental apartment with terrace | Close to John Hancock Center | City view

Rush & Division, Chicago, Illinois, United States
$467
per night
Outstanding(7 ratings)
$467
per night
View deal
Condo Lincoln Park
Sep 19 - Sep 26
Condo ∙ 8 guests ∙ 5 bedrooms

Family-friendly condo with garden & patio

Lincoln Park, Chicago, Illinois, United States
$506
per night
Outstanding(37 ratings)
$506
per night
View deal
House Douglas
-28%
Jun 10 - Jun 17
House ∙ 6 guests ∙ 3 bedrooms

Lovely house with garden | Suitable for remote work

Douglas, Chicago, Illinois, United States
$440$134
per night
$440$134
per night
View deal
Apartment Near North
Sep 19 - Sep 26
Apartment ∙ 7 guests ∙ 2 bedrooms

Holiday apartment with terrace | Near John Hancock Center | City view

Near North, Chicago, Illinois, United States
$142
per night
Good(22 ratings)
$142
per night
View deal
House Avalon Park
Sep 19 - Sep 26
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly vacation home | Suitable for remote work

Avalon Park, Chicago, Illinois, United States
$469
per night
Outstanding(1 rating)
$469
per night
View deal
Apartment Wicker Park
-24%
Jul 3 - Jul 10
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment | Good for workation

Wicker Park, Chicago, Illinois, United States
$573$420
per night
Excellent(4 ratings)
$573$420
per night
View deal
Condo East Village
Sep 19 - Sep 26
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with patio & BBQ | Suitable for remote work

East Village, Chicago, Illinois, United States
$634
per night
$634
per night
View deal
Apartment Heart of Chicago
Jul 12 - Jul 19
Apartment ∙ 8 guests ∙ 2 bedrooms

Holiday apartment with patio, grill & hot tub

Heart of Chicago, Chicago, Illinois, United States
$182
per night
Outstanding(5 ratings)
$182
per night
View deal
Apartment North Center
-26%
Sep 19 - Sep 26
Apartment ∙ 6 guests ∙ 5 bedrooms

Fully equipped wonderful apartment with grill, terrace & garden

North Center, Chicago, Illinois, United States
$631$239
per night
Outstanding(13 ratings)
$631$239
per night
View deal
Condo Park West
Sep 19 - Sep 26
Condo ∙ 12 guests ∙ 4 bedrooms

Child-friendly spacious condo with garden | Suitable for remote work

Park West, Chicago, Illinois, United States
$597
per night
Outstanding(2 ratings)
$597
per night
View deal
Apartment Streeterville
Aug 15 - Aug 22
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with terrace | Close to John Hancock Center | City view

Streeterville, Chicago, Illinois, United States
$484
per night
Outstanding(60 ratings)
$484
per night
View deal
House Portage Park
Aug 2 - Aug 9
House ∙ 8 guests ∙ 4 bedrooms

House with 4 rooms for 8 persons

Portage Park, Chicago, Illinois, United States
$152
per night
$152
per night
View deal
Apartment Washington Park
Sep 19 - Sep 26
Apartment ∙ 3 guests ∙ 3 bedrooms

Holiday apartment with barbeque & terrace | Suitable for remote work

Washington Park, Chicago, Illinois, United States
$103
per night
$103
per night
View deal
House West Chesterfield
Aug 2 - Aug 9
House ∙ 10 guests ∙ 5 bedrooms

House with hot tub

West Chesterfield, Chicago, Illinois, United States
$226
per night
$226
per night
View deal

Vacation homes and rentals with a yard

House  Old Town
Jul 26 - Aug 2
$350
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Vacation Home with Grill, Patio & Yard | Lake View | Pets Are Welcome

4.8
Outstanding(140 ratings)
Old Town, Chicago, Illinois, United States
Yard
View deal
House  Oakland
Jun 28 - Jul 5
$505
per night
House ∙ 10 guests ∙ 7 bedrooms

Vacation Home with Terrace, Barbeque & Yard | Lake View

4.9
Outstanding(12 ratings)
Oakland, Chicago, Illinois, United States
Yard
View deal
House  Grand Boulevard
Jul 12 - Jul 19
$535
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-Oriented Charming House with Barbeque & Garden | Perfect for Remote Work | Pet-Friendly

5.0
Outstanding(7 ratings)
Grand Boulevard, Chicago, Illinois, United States
Yard
View deal
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Best Vacation Home Deals in Chicago

Save up to 47%

Apartment Chicago Loop
Mar 23 - Mar 30
-47%
$789
$538
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with Terrace & Pool | Next to Cloud Gate | City View

5.0
Outstanding(47 ratings)
Chicago Loop, Chicago, Illinois, United States
View deal
Apartment Streeterville
Sep 2 - Sep 9
-37%
$969
$440
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
Apartment Near North Side
Mar 23 - Mar 30
-44%
$950
$945
per night
Apartment ∙ 11 guests ∙ 3 bedrooms

Fully Equipped Apartment with Patio | City View

4.5
Excellent(40 ratings)
Near North Side, Chicago, Illinois, United States
View deal

Discover a vacation rental fitting your needs among the 11,235 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 47%.

Budget-friendly Vacation Rentals in Chicago

Find Fantastic yet Inexpensive Offers

Condo Rogers Park
Jul 7 - Jul 14
$231
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Patio | Perfect for Remote Work

4.7
Excellent(23 ratings)
Rogers Park, Chicago, Illinois, United States
View deal
House Near North Side
Jun 28 - Jul 5
$793
per night
House ∙ 14 guests ∙ 3 bedrooms

Fully Equipped House with Patio | City View

4.7
Excellent(27 ratings)
Near North Side, Chicago, Illinois, United States
View deal
Condo Rogers Park
Sep 6 - Sep 13
$297
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Fully Equipped Condo with BBQ, Yard & Jacuzzi | Nature View | Dogs Allowed

4.9
Outstanding(242 ratings)
Rogers Park, Chicago, Illinois, United States
View deal

Top-Rated Rentals and Accommodations in Chicago

Book Vacation Rental Offers with the Highest User Rating

House Belmont Central
Mar 19 - Mar 26
$393
per night
House ∙ 16 guests ∙ 7 bedrooms

House with 7 rooms for 16 persons

5.0
Outstanding(7 ratings)
Belmont Central, Chicago, Illinois, United States
View deal
House Edgewater Beach
Dec 27 - Jan 3
$389
per night
House ∙ 12 guests ∙ 6 bedrooms

Family-oriented vacation home with terrace & barbecue | Perfect for remote work | Pets are welcome

5.0
Outstanding(4 ratings)
Edgewater Beach, Chicago, Illinois, United States
View deal
House Lincoln Park
Mar 19 - Mar 26
$451
per night
House ∙ 24 guests ∙ 4 bedrooms

Family-friendly vacation home with BBQ, patio & garden | Lake view | Suitable for remote work

5.0
Outstanding(190 ratings)
Lincoln Park, 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 $331
per night
HomeToGo
Apartment ∙ 12 guests ∙ 4 bedrooms
4.7
Excellent(3 ratings)
South Austin, Chicago, Illinois, United States
View deal
from $331
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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Verified reviews

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

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

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

Popular Rental Amenities in Chicago

  • WiFi (10,630)
  • Pool (2,548)
  • Parking (1,742)
  • Pet-friendly (4,680)
  • Kitchen (6,495)
  • TV (9,806)
  • Air conditioning (10,691)
  • Balcony/patio (2,617)
  • Washing machine (5,879)
  • Microwave (5,984)
  • Hot tub (415)
  • Fireplace (1,465)

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 8, 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 $718 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 $132 per night in January (1/3 – 1/10).

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 January (1/3 – 1/10), as 92% of the rentals are booked. It is easier to find a rental in a week of March (3/29 – 4/5), as only 30% 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 11,235 rentals
💳 Possible discounts up to 47%
🌙 Nightly prices starting at $80
⭐ Popular amenities Internet, Pool and Parking
🐾 Pet friendly homes 4,644 homes
🏊 Vacation rentals with pools 2,549 homes
5,842,297 reviews
Chicago vacation rentals have an average rating of 4.3/5 on 5,842,297 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 $80. Average prices for apartment rentals are $388 per night. House rentals in Chicago cost on average $583 per night.

How many vacation homes are available for booking in Chicago?

Currently there are 11,235 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 2,549 vacation rentals from 24 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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