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

Discover a selection of 1366 homes, 2461 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.

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Find the best place to stay - Chicago

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

Sleeps 4 · 1 bedroom · 1 bathroom

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)
Oak Brook Golf Course (15.7 mi / 25.3 km)
Home Alone House (16.7 mi / 26.9 km)
The Glen Club (17.7 mi / 28.5 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 Robert Brooks Homes?

The average price for a holiday home in Robert Brooks Homes is based on several factors, including length of stay, property type and season. Whether you're looking for a sprawling villa with lots of bedrooms or a quaint cabin for just you and your sweetheart, just enter your travel dates to view stays with amazing value.

How much does it cost to rent a beach house in Robert Brooks Homes?

The average price for a holiday home close to the beach in Robert Brooks Homes depends on when you're travelling and the size and type of property you're looking for. You can find prices easily and quickly on Stayz by entering your dates of travel. Then use our filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a pool.

What are the top attractions for families in Robert Brooks Homes?

You'll find loads of fabulous things to see and do with the family in Robert Brooks Homes, including:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

How old do you have to be to rent a holiday home in Robert Brooks Homes?

The minimum age can vary across properties on Stayz, so be sure to check the rules of the holiday home in Robert Brooks Homes you want to book. But usually, it's 16, 18 or 21.

How long can I rent a holiday home in Robert Brooks Homes for?

The amount of time you can stay in a Robert Brooks Homes holiday home for is up to each property. Just tap in your preferred travel dates to view available options that offer extended stays. They include all you require to make your extended break more comfortable and enjoyable, such as kitchens and laundries. Some Stayz holiday homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.