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How many holiday accommodation are available around Downtown Chicago?

Our 2020 accommodation listings offer a large selection of 1,087 holiday rentals around Downtown Chicago. From 12 townhouses to 882 flats & apartments, find unique holiday homes for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular destinations to visit in Downtown Chicago?

There are many lovely places to stay for a long holiday or just a weekend break in Downtown Chicago. From Stayz travellers, the popular destinations to visit are:

  • The Loop: 609 holiday rentals
  • West Loop: 477 holiday rentals
  • Logan Square: 314 holiday rentals
  • Near South Side: 576 holiday rentals
  • Printers Row: 240 holiday rentals

Stayz offers you the possibility to discover many other popular destinations in Downtown Chicago! Please use our search bar to access the selection of holiday rentals available in other popular destinations.

What are the main cities to discover in Downtown Chicago?

Whether you are travelling solo or with family and friends, here are the cities in Downtown Chicago with the largest selection of holiday rentals for a perfect city break:

  • Glenview: 247 holiday homes
  • Evanston: 997 holiday homes
  • Oak Park: 1,154 holiday homes
  • Forest Park: 1,220 holiday homes
  • Rosemont: 267 holiday homes

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

Can I find easy access holiday homes when travelling by plane to Downtown Chicago?

Yes of course. Our owners offer a large selection of holiday homes near to airports. Airports with a large selection of rentals in Downtown Chicago are:

  • Gary, IN (GYY-Gary - Chicago Intl.): 222 holiday houses
  • Chicago, IL (ORD-O'Hare Intl.): 1,364 holiday houses
  • Chicago, IL (MDW-Midway Intl.): 1,382 holiday houses

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

Near which points of interest can I spend my holidays in Downtown Chicago?

Stayz offers a large selection of holiday homes near great places to visit in Downtown Chicago. From Stayz travellers, the more popular points of interest to stay for a holiday trip or just for a weekend are:

  • Harvey Community Center: 546 holiday rentals
  • 311 S Wacker Dr: 1,364 holiday rentals
  • Wrigley Building: 1,359 holiday rentals
  • Chicago McCormick Place Station: 1,354 holiday rentals
  • Harvey 147th Street-Sibley Boulevard Station: 730 holiday rentals

But there are many other points of interest around Downtown Chicago listed on Stayz where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection of holiday homes.

Explore destinations around Downtown Chicago

Glenview
247 holiday rentals
Evanston
997 holiday rentals
Oak Park
1,154 holiday rentals
Forest Park
1,220 holiday rentals
Rosemont
267 holiday rentals
Des Plaines
226 holiday rentals
Orland Park
24 holiday rentals
Skokie
723 holiday rentals
Park Ridge
454 holiday rentals
Midlothian
31 holiday rentals
Gary
96 holiday rentals
Oak Lawn
140 holiday rentals
Niles
644 holiday rentals
Melrose Park
642 holiday rentals
Dolton
52 holiday rentals
Northlake
224 holiday rentals
Lincolnwood
976 holiday rentals
Western Springs
136 holiday rentals
Elmwood Park
913 holiday rentals
Winnetka
168 holiday rentals