Discover a selection of 1,500 holiday rentals in Chicago, IL, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 124 per night, and flats & apartments and houses are popular options for a stay in Chicago. Either way, you'll find a rental for everyone's needs.
Destination guide

The vibrant city of Chicago awaits you

Come and experience Chicago and its architecture, theatre scene and museums. This cosmopolitan and scenic city is well known for its art, monuments and entertainment. Chicago Cultural Center, Ford Center for the Performing Arts Oriental Theatre and Chicago Theatre are a few of the top cultural sights. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Sightseeing in and around Chicago

Are you hoping to discover attractions to see in the area? 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 explore, all within 30 miles (48.2 km) of the city centre:

  • Skydeck Ledge (0.4 mi / 0.6 km)
  • Navy Pier (1.2 mi / 1.9 km)
  • John G. Shedd Aquarium (1.2 mi / 2 km)
  • Adler Planetarium and Astronomy Museum (1.5 mi / 2.4 km)
  • Lincoln Park Zoo (2.7 mi / 4.4 km)
  • Brookfield Zoo (11 mi / 17.7 km)
Natural features

Exploring the natural landscape of Chicago

Whether you're an active traveller or just want to spend some time taking in the scenery, Chicago is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (0.2 mi / 0.4 km)
  • Grant Park (0.7 mi / 1 km)
  • Lincoln Park (4.8 mi / 7.8 km)
  • Chicago Riverwalk (0.5 mi / 0.8 km)
  • Ohio Street Beach (1.2 mi / 1.9 km)
  • Northerly Island Park (1.5 mi / 2.4 km)
How to get there

How to get to and around Chicago

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 8.6 mi (13.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Chicago, IL (ORD-O'Hare Intl.), 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 in the area. You can get around Chicago by jumping on the metro at Monroe Station, Monroe Station or Adams-Wabash Station.

Can I find a vacation rental around Chicago?

Yes, our 2020 property listings offer a large selection of 1,453 vacation rentals near Chicago. From 1,086 flats & apartments to 248 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chicago for a holiday or a weekend are on Vrbo.

What is the best area to stay when traveling to Chicago?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chicago:

  • The Loop: 625 vacation rentals
  • Near North Side: 575 vacation rentals
  • Washington Park: 15 vacation rentals
  • West Town: 532 vacation rentals
  • Bucktown: 51 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Chicago?

Vrbo UK offers a large selection of vacation rentals near lovely places in Chicago. From Vrbo UK travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Garfield Park: 1,429 vacation rentals
  • Jackson Park: 1,221 vacation rentals
  • Chicago 103rd Street Station (Rosemoor): 1,325 vacation rentals
  • Grant Park: 1,070 vacation rentals
  • McCormick Place: 1,123 vacation rentals

But there are many other points of interest around Chicago listed on Vrbo UK where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Flats in Chicago?

Yes, of course. Vrbo UK has 1,086 Flats in Chicago. Our other popular types of vacation rentals in Chicago include:

  • Houses: 248 rentals available
  • Cabins: 4 rentals available
  • Studios: 1,017 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cottages and more.

Can I find a vacation rental with pool in Chicago?

Yes, you can select your preferred vacation rental with pool among our 151 vacation rentals with pool available in Chicago. Please use our search bar to access the selection of vacation rentals available.

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