calm body of water near building base64Hash calm body of water near building

Chicago Vacation Rentals

Find 15 available home rentals from 18 partners
Anytime
Guests
Anytime
Guests

Top 15 Recommended vacation rentals in Chicago

Find your perfect vacation rental in Chicago from just $38 per night!

House Oak Park
-50%
May 1 - May 8
House ∙ 9 guests ∙ 3 bedrooms

139 m² House

Oak Park, Oak Park Township, Illinois, United States
$563$283
per night
$563$283
per night
View deal

Vacation rentals and apartments with air conditioning

House  Oak Park
from $238 per night
5 guests ∙ 2 bedrooms

House

4.9
Outstanding(10 ratings)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
View deal
House  Oak Park
from $573 per night
House ∙ 8 guests ∙ 4 bedrooms

82 m² House

4.8
Outstanding(13 ratings)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
View deal
House  Berwyn
from $372 per night
8 guests ∙ 3 bedrooms

House

3.0
(2 ratings)
Berwyn, Cook County, Illinois, United States
Air conditioning
View deal
See all offers

Apartments with a balcony or patio

Apartment  Berwyn
from $224 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

112 m² Apartment

5.0
Outstanding(17 ratings)
Berwyn, Cook County, Illinois, United States
Balcony/Patio
View deal
House  Berwyn
from $403 per night
House ∙ 8 guests ∙ 4 bedrooms

167 m² House

5.0
Outstanding(25 ratings)
Berwyn, Cook County, Illinois, United States
Balcony/Patio
View deal
House  Cicero
from $432 per night
House ∙ 6 guests ∙ 4 bedrooms

125 m² House

Cicero, Cicero Township, Illinois, United States
Balcony/Patio
View deal
See all offers

Vacation homes and cottages with a garden

Apartment  Stickney
from $213 per night
4 guests ∙ 2 bedrooms

Apartment

4.1
Very good(13 ratings)
Stickney, Stickney Township, Illinois, United States
Yard
View deal
House  Cicero
from $325 per night
House ∙ 8 guests ∙ 5 bedrooms

139 m² House

Cicero, Cicero Township, Illinois, United States
Yard
View deal
Condo  Oak Park
from $241 per night
Condo ∙ 11 guests ∙ 3 bedrooms

121 m² Condo

5.0
Outstanding(1 rating)
Oak Park, Oak Park Township, Illinois, United States
Yard
View deal
See all offers

Best Vacation Home Deals in Chicago

Save up to 43%

House Fifth City
Jan 31 - Feb 7
-43%
$474
$271 per night
House ∙ 5 guests ∙ 3 bedrooms

139 m² House

5.0
Outstanding(7 ratings)
Fifth City, Chicago, Illinois, United States
Free cancellation
View deal

15 beautiful vacation rentals from 18 vacation rental websites, including Booking.com and HomeToGo, are available in Chicago. Using HomeToGo you can directly search and compare the prices of each listed property to find the best deal and save up to 43%.

Budget-friendly Rentals in Chicago

Find Fantastic yet Inexpensive Rentals

House Cicero
May 23 - May 30
$660 per night
House ∙ 6 guests ∙ 2 bedrooms

125 m² House

Cicero, Cicero Township, Illinois, United States
View deal

Top-Rated Offers and Accommodations in Chicago

Book Vacation Rentals with the Highest User Rating

House Lincoln Park
from $465 per night
House ∙ 24 guests ∙ 4 bedrooms

390 m² House

5.0
Outstanding(191 ratings)
Lincoln Park, Chicago, Illinois, United States
View deal
Apartment Streeterville
from $469 per night
Apartment ∙ 6 guests ∙ 4 bedrooms

139 m² Apartment

4.7
Excellent(31 ratings)
Streeterville, Chicago, Illinois, United States
View deal
Apartment Chicago Loop
from $859 per night
Apartment ∙ 12 guests ∙ 6 bedrooms

223 m² Apartment

4.6
Excellent(23 ratings)
Chicago Loop, 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 $473 per night
HomeToGo
Apartment ∙ 12 guests ∙ 4 bedrooms
4.7
Excellent(3 ratings)
South Austin, Chicago, Illinois, United States
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

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 (5)
  • Pool (3)
  • Kitchen (3)
  • TV (4)
  • Air conditioning (5)
  • Parking (2)
  • Washing machine (2)
  • Pet-friendly (3)
  • Microwave (3)
  • Dishwasher (3)
  • No smoking (5)
  • Grill (1)

Chicago is a wonderful vacation spot if you want an accommodation with a pool, as 0% of the vacation rentals there have one. Interestingly, our data shows that more hotel room have a pool than apartment rental. Additionally, they can welcome 8 vacationers, on average, while apartment rental with pools can host an average of 4 people. many of Chicago's vacation homes including a pool are located within two kilometres of water, choose between some pool time or waterfront moments.

Price and Availability Index in Chicago

Click on any bar to see price and availability information

Vacation Rental Price Information in Chicago

We analyzed vacation homes, cottages and apartments to display a price graph showing the average price per night in Chicago. The week with the highest average prices is in August (8/2 – 8/9). During this week, a night will cost on average $704. Prices decrease in a week of April (4/19 – 4/26), where average prices are $586.

Rental availability information in Chicago

Have a look at the above graph to see the global availability of vacation rentals in Chicago. The week with the highest booking rate is in April (4/4 – 4/11). Only 12% of the rentals are still available. On the other hand, the week with the most available offers is in July (7/12 – 7/19).

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 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?

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.

5,652,166 reviews
Chicago vacation rentals have an average rating of 4.3/5 on 5,652,166 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Chicago?

At the moment, there are 15 vacation homes from 18 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 0% 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.

Discover more vacation accommodations

Top Vacation Destinations

Top cities to visit

image-tag