Discover a selection of 2,000 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 £ 87 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.
Top rated rentals — Chicago
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.

How many holiday rentals are available around Chicago?

Our 2021 accommodation listings offer a large selection of 1,862 holiday lettings around Chicago. From 1,490 flats & apartments to 322 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Chicago:

  • Rogers Park: 81 holiday homes
  • Wicker Park: 806 holiday homes
  • Bridgeport: 26 holiday homes
  • Logan Square: 467 holiday homes
  • River North: 609 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Chicago?

Vrbo UK offers a large selection of holiday accommodations near great places in Chicago. From Vrbo UK travellers, the most popular points of interest to stay near are:

  • Jackson Park: 1,774 holiday lettings
  • Grandparents Park: 1,857 holiday lettings
  • Chicago 87th Street Station (Woodruff): 1,774 holiday lettings
  • 311 S Wacker Dr: 1,800 holiday lettings
  • Original Playboy Mansion: 1,803 holiday lettings

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 holiday rentals available near the point of interest of your choice.

Can I rent Flats in Chicago?

Yes, of course. Vrbo UK offers 1,490 Flats in Chicago. Our other popular types of Chicago holiday rentals include:

  • Houses: 322 self catering accommodations
  • Cabins: 7 self catering accommodations
  • Studios: 1,245 self catering accommodations

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

Can I find a holiday accommodation with pool in Chicago?

Yes, you can select your preferred holiday accommodation with pool among our 318 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

Explore destinations around Chicago

Rogers Park
81 holiday rentals
Wicker Park
806 holiday rentals
26 holiday rentals
Logan Square
467 holiday rentals
River North
609 holiday rentals
The Loop
778 holiday rentals
66 holiday rentals
West Town
860 holiday rentals
Ukrainian Village
389 holiday rentals
Noble Square
138 holiday rentals
Near North Side
719 holiday rentals
294 holiday rentals
Grand Boulevard
29 holiday rentals
Old Town Chicago
322 holiday rentals
Roscoe Village
195 holiday rentals
311 holiday rentals
Irving Park
34 holiday rentals
South Loop
249 holiday rentals
Theatre District
389 holiday rentals
East Hyde Park
33 holiday rentals