Chicago, Illinois holiday accommodation: short-term house rentals & properties

Discover a selection of 1355 homes, 2447 apartments and other holiday rentals in Chicago that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a fireplace. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find the best place to stay - Chicago

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 bedroom · 1 bathroom

Find spaces that suit your style

Top rated rentals - Chicago

Premier Host

Lovely stay in a nice neighbourhood which felt like a home as had everything you need.

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Travel to vibrant Chicago

Take a holiday to Chicago and enjoy the area's theatre scene, architecture and museums. This city is cosmopolitan and scenic, recognised for its art, monuments and entertainment. Navy Pier and Michigan Avenue are a couple of places to search for that perfect souvenir. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Chicago

Are you hoping to discover attractions to visit during your stay? Venture out of your holiday home and check out everything that makes Chicago a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

Dave & Buster's (1.4 mi / 2.3 km)
Lincoln Park Zoo (2.8 mi / 4.5 km)
Galloping Ghost (12.5 mi / 20.1 km)
The Dome at the Parkway Bank Sports Complex (14.4 mi / 23.2 km)
Oak Brook Golf Course (15.7 mi / 25.3 km)
Home Alone House (16.7 mi / 26.9 km)

Exploring the natural features in Chicago

Whether you're an outdoor enthusiast or just want to take in the scenery, Chicago is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Grant Park (0.7 mi / 1 km)
Millennium Park (0.3 mi / 0.5 km)
Maggie Daley Park (0.5 mi / 0.8 km)
Ohio Street Beach (1.2 mi / 1.9 km)
Oak Street Beach (1.6 mi / 2.5 km)
Northerly Island (1.7 mi / 2.8 km)

Transport options to and around Chicago

Fly into Chicago Midway Airport (MDW), the closest airport, located 8.6 mi (13.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago O'Hare International Airport (ORD), which is 15.7 mi (25.3 km) away.

If you're travelling by train, Millennium Station, Chicago Van Buren Street Station and Chicago Union Station are the main stations that serve the city. It's easy to get around Chicago by jumping on the metro at Monroe Station (Red Line), Monroe Station (Blue Line) or Adams-Wabash Station.

Frequently asked questions

How much does it cost to rent a holiday home in Dearborn Park?

Different factors can determine how much you'll pay for a holiday home in Dearborn Park, such as the season, type of property and length of stay. However, all our holiday homes have one thing in common — unbeatable value. Simply enter your travel dates to find your perfect match.

How much does it cost to rent a beach house in Dearborn Park?

Prices for beach houses in Dearborn Park vary depending on the size and style of the property and time of year you're travelling. Simply enter your travel dates into Stayz and how many guests to view your holiday home options and prices. From there you can use the filters to refine your search by nearby activities, ratings, amenities and more.

What are the top attractions for families in Dearborn Park?

Keep your kids entertained at these top family-friendly attractions in Dearborn Park:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

How old do you have to be to rent a holiday home in Dearborn Park?

We advise checking with the Dearborn Park holiday property you're considering on Stayz as the age limit differs. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in Dearborn Park for?

The amount of time you can book a Dearborn Park holiday home for depends on the property. Simply put in your dates of travel to view options offering extended stays. They include everything you need to make your extended getaway more convenient and enjoyable, like air conditioning and kitchens. Some properties might also offer weekly or monthly discounted prices, so you can stay longer for less money.