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, Booking.com and more.
Airbnb Chicago, ILVrbo Chicago, ILBooking.com Chicago, ILOutdoorsy Chicago, ILRvshare.com Chicago, IL
And more...

Find the best vacation rental

ACCOMMODATION TYPES

Save Up To 76%

Best Cheap Vacation House & Condo Rental Deals near Chicago, IL

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.

How can a family plan their 7 day trip in Chicago, IL?

An Ideal Family Trip Itinerary for 7 Days in Chicago, IL

Chicago is a vibrant city that offers something for everyone. From the stunning skyline to world-class museums and attractions, there's plenty of fun activities that are perfect for families. This 7 day itinerary will take you through some of the best places that Chicago has to offer.
  • DATE
    1
    Day 1: Exploring the Windy City
    Start your trip by exploring the historic Navy Pier. Take a stroll along the pier and enjoy the beautiful views of Lake Michigan. Afterward, head over to the iconic Willis Tower Skydeck and get an amazing view of the entire city. Make sure to check out the interactive exhibits and games at the Museum of Science and Industry.
  • DATE
    2
    Day 2: Touring Around Downtown
    Spend the day discovering the many attractions downtown. Start off with a visit to the Shedd Aquarium and see the incredible sea life. Then, go on a boat tour around the city and admire the architecture from the water. Finish up your day with a walk around Millennium Park and taking pictures of the Cloud Gate sculpture.
  • DATE
    3
    Day 3: Visiting the North Side
    Head up north and explore the Lincoln Park Zoo. See all kinds of animals from around the world and observe them in their natural habitats. Then, take a leisurely stroll through the Lincoln Park Conservatory and admire the lush greenery. Don't forget to stop by Wrigley Field and take a picture outside the famous baseball stadium.
  • DATE
    4
    Day 4: Shopping and Dining
    Take a break and do some shopping at The Magnificent Mile. Here, you'll find all kinds of stores and boutiques to browse through. Later, indulge in some delicious food at one of the many restaurants in the area. End your night with a show at the Broadway Playhouse or catch a movie at AMC River East 21.
  • DATE
    5
    Day 5: Have Fun at the Beach
    Pack your swimsuits and spend the day at North Avenue Beach. Enjoy a picnic lunch under the sun and play some beach volleyball with friends and family. Relax and soak up some sun before heading back home.
  • DATE
    6
    Day 6: Take a Day Trip Out of Town
    Go for a day trip to Galena, Illinois. Here, you can explore the charming town and learn about its history. Visit the Ulysses S. Grant Home and learn more about the former president. Afterwards, taste some local wines and shop for souvenirs at the Main Street shops.
  • DATE
    7
    Day 7: A Relaxing Day
    End your trip with a relaxing day at Garfield Park Conservatory. Enjoy the tranquil atmosphere and admire the exotic plants. Spend the afternoon strolling through the park and taking pictures of the beautiful flowers.

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.
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
* 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