Discover the best deals from millions of vacation homes

Here at VacationHomeRents, you can easily find and compare the best vacation apartments, cabins, house boats, beach houses, and RV deals. By a simple click, we help you search among millions of listings across the top sites like Airbnb, Vrbo, and more.
Airbnb Chicago, ILVrbo Chicago, Chicago, ILOutdoorsy Chicago, IL
And more...

Find the best vacation rental


What Are The Top Amenities at Chicago, IL?

Amenity Overview in Chicago, IL

There are in total of 15 rental amenities in Chicago, shown above with the property numbers. In Chicago, 1671 rentals offer Internet or Wifi, 1453 rentals offer Air Conditioning, 1386 rentals offer TV. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Fireplace.

Which Price Range Is Considered As A Good Deal in Chicago, IL Area?

Vacation Apartment & House Rental Price Information in Chicago, IL

The graph shows the percentages of vacation homes in each price bucket. Chicago has the largest percentage (27.59%) of homes in $100 - $150 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
What Are The Most Liked Rental Accommodations in Chicago, IL?
Most Picked Accommodations in Chicago, IL
Before visiting Chicago, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: Apartment, House, Studio, Condo, Townhome, Guest House, Hotel, Building, Bungalow, Corporate Apartment, Tower, Resort, Bed And Breakfast, Yacht, Hotel Suites, Estate, Cottage. Apartment is the most-liked rental type, with the largest percentage of 57.42%. The biggest home in this area available for rent is around 21528 square feet.The least popular accommodation in Chicago is Cottage rentals
How Many Accommodations Are Pets Allowed in Chicago, IL?
Pets Allowed vs Not Allowed in Chicago, IL
17.57% of vacation homes in Chicago are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Best Tourist Attractions in Chicago, IL?
Tourist Attractions In Chicago, IL

Here we list the must-visit places in Chicago:

Trail Recommendations in Chicago, IL Area?
Must Visit Trails In Chicago, IL
If you like outdoor activities, we highly recommend you to visit those famous trails: Wicker Park Trail, Chicago Riverwalk to Grant Park Trail, Public Outdoor Art Walking Tour, Millennium Park Trail, Museum and Lakefront Walking Tour, Chicago Riverwalk, Navy Pier Walk, Magnificent Mile and Navy Pier - Chicago, Lincoln Park Trail, Wrigleyville Cultural Walking Tour.
Where Are The Campgrounds in Chicago, IL Area?
Top Rated Campgrounds In Chicago, IL
For campgrounds in Chicago, here are our recommendations: Indian Creek, Lakeshore East, Illinois Beach Campground, Chicago Northwest KOA, Cliffside Park Campground, Indiana Dunes Campground, Cedar Lake, Kankakee River Campground, Warren Dunes Campground, Rutherford Mountain Campground.
Which Airports Should I Choose To Get To Chicago, IL?
Suggested Airports in Chicago, IL

4 airport(s) close to Chicago are:

What are the activities in Chicago, IL that are family friendly?
Family Friendly Activities

Navy Pier Park: there is a Ferris wheel (the most beautiful night scene), a music carousel, 18 holes mini-golf course, and a 1500 seat outdoor performance area. You can also take cruises or speedboats to enjoy Lake Michigan. Tickets are free.

Shedd Aquarium: the largest indoor aquarium in the world and a paradise for children. There is a discount for online tickets.

Lincoln Park: the largest park in Chicago, the most famous of which is Lincoln Park Zoo and greenhouse botanical garden. Every autumn, there is a lighting festival in Lincoln Park. Free play.

Where to visit in order to explore art and culture in Chicago, IL?
Art & Culture Places

The Art Institute Chicago: the collection time span from ancient Egyptian pottery in 3000 BC to contemporary pop art. 

The University of Chicago: it is one of the most famous universities in the world and one of the world's economic research centers. There are abundant Gothic buildings on campus. Free, open all day.

Chicago Theater: known as the "miracle of the world theater", it is a landmark building in Chicago. Whether it's a concert, a comedy, or a movie, there's always something you like.

What are the nightlife spots in Chicago, IL?
Nightlife Spots

The Aviary: the unique molecular cocktail bar.

Three Dots and a Dash: top-rated bar.

House of Blues: the decoration is very unique, you can enjoy the charm of music quietly.

What does the calendar look like for local events & festivals in Chicago, IL?
Local Events & Festivals

Windy City Smokeout: May - September is the most popular.

Chicago Food Festival: around July. There will also be outdoor concerts and various art exhibitions during the festival.

What are the travel peak seasons in Chicago, IL?
Peak Seasons

Weather: from May to September, the weather changes rapidly, so you should take rain gear with you; from October to January of the next year, in addition to cold, there is also strong wind. Therefore, in addition to keeping warm, clothes should be windproof.

The best travel time: April to June is the warmest and most comfortable climate, which is very suitable for traveling. 

What are the must-visit places in Chicago, IL?
Must See Attractions

Millennium Park: located in the center of downtown Chicago, in addition to modern sculptures and buildings, there are also rich activities such as public interactive art, outdoor food, and classical music, including Jay Pritzker Music Pavilion, Cloud Gate, and Crown Fountain. Tickets are free.

The Field Museum: the museum's dinosaur exhibition is the world's most famous and must not miss. Tickets can be divided into pass tickets and ordinary tickets.

Adler Planetarium: it includes two pavilions, a high-tech star rider cinema, and an interactive Astronomical Museum, displaying various scientific instruments of historical significance. Here you can see Chicago's premier skyline.

John Hancock Center: known as the "city in the city", you can enjoy the scenery of four states on the 94th floor, the signature room bar on the 95th floor, or the highest indoor swimming pool in the United States on the 44th floor.

Where are the hidden gems or unique spots to visit in Chicago, IL?
Hidden Gems

Willis Tower: The 103 story transparent glass viewing platform is the best viewing point, which can give you a panoramic view of the whole city.

Richard H. Driehaus Museum: the glass dome inside is highly recommended, and the artworks, wallpaper, and wood carvings inside are worthy of close inspection and appreciation.

Chicago Helicopter Experience: a great experience to overlook the city.

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers