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How many holiday rentals are available around Downtown Chicago?

Our 2020 accommodation listings offer a large selection of 1,154 holiday lettings around Downtown Chicago. From 12 townhouses to 937 flats & apartments, 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.

Can I rent a city-centre property in Downtown Chicago?

There are tons of reasons to stay somewhere central when you visit a new city, but no one can argue with the number one draw — location, location, location! HomeAway has 148 city centre holiday rentals available. Open to more suggestions? HomeAway is brimming with other property options to look through, including:

  • 55 town holiday accommodation options.
  • 49 lakeside holiday accommodation options.
  • 42 lake-view holiday accommodation options.

Can I rent an apartment in Downtown Chicago?

Unpack your bag, check out the view and turn the kettle on. If you're after a place with all the conveniences of home, an apartment rental is an awesome way to go. HomeAway has 1,048 for you to browse here. If you book soon, you could spend as little as £38 per night. Or maybe you'd rather choose one of the area's other self-catering accommodation options, such as:

  • House: 191 self-catering accommodation options. Prices start from £38 per night.
  • Condo: 191 self-catering accommodation options. Prices start from £58 per night.
  • Hotel: 87 self-catering accommodation options. Prices start from £79 per night.

Can I stay in Downtown Chicago in a large group?

Nothing beats reuniting with your old friends or spending a week or so with your beloved relatives in a marvellous new place. And the best thing, HomeAway has places to suit. At the moment, apartment holiday rentals are all the rage for large groups of visitors here, and you'll find 257 featured on our database. In and around the area, the properties that are suitable for large groups of guests include:

  • If yours is a crew of 6, we have 376 rental accommodation suited to that size. Book a night for as little as £38.
  • If you have 8 in your party, you'll be happy to hear that there are 180 rental accommodation that are suitable. The starting price is £61 per night.
  • Planning a trip away with a group of 5? We have 135 accommodation for rent that will be perfect. Prices begin at just £58 per night.

You and the squad will be well looked after when you plan your Downtown Chicago travels through us!

Explore destinations around Downtown Chicago

Evanston
1,112 holiday rentals
Forest Park
1,398 holiday rentals
Dolton
94 holiday rentals
Northbrook
166 holiday rentals
Gary
131 holiday rentals
Winnetka
257 holiday rentals
Elmwood Park
1,215 holiday rentals
Oak Park
1,454 holiday rentals
Tinley Park
30 holiday rentals
Highland Park
155 holiday rentals
Skokie
960 holiday rentals
Orland Park
72 holiday rentals
Wilmette
479 holiday rentals
Deerfield
78 holiday rentals
Rosemont
420 holiday rentals
Hammond
138 holiday rentals
Des Plaines
384 holiday rentals
Glenview
401 holiday rentals
Wheeling
146 holiday rentals
Morton Grove
645 holiday rentals