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 2020 accommodation listings offer a large selection of 1,223 holiday lettings around Chicago. From 756 flats & apartments to 239 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.

Can I rent a city-centre property in Chicago?

If you're into the thought of jumping out of bed and discovering shops, bars and attractions within a couple of minutes, then you'll want to stay central. HomeAway has 165 centrally located holiday properties available. Open to more suggestions? HomeAway is brimming with other property options to investigate, including:

  • 83 town holiday accommodation options.
  • 58 lakeside holiday accommodation options.
  • 49 lake-view holiday accommodation options.

Can I rent an apartment in Chicago?

There's no need to miss out on all the conveniences of home just because you're on holiday. Sit back and relax in your very own apartment and experience the area like the locals. HomeAway has 1,166 for you to check out here. How does £27 per night sound? That's what you're looking at spending if you don't put it off for too long! If that doesn't agree with your squad's taste, we have a range of other self-catering accommodation options to choose from, such as:

  • Hotel: 311 self-catering accommodation options. Prices start from £28 per night.
  • House: 288 self-catering accommodation options. Prices start from £35 per night.
  • Condo: 238 self-catering accommodation options. Prices start from £39 per night.

Can I stay in Chicago in a large group?

The recipe for a perfect escape is relaxing with your friends and loved ones in a completely new place. If you're travelling with a large group, HomeAway can help out. Presently, apartment holiday rentals are preferred for big groups of travellers here, and we have 298 available on our database. The rental property options that can provide for large groups in this area include:

  • If yours is a group of 6, we offer 483 properties to rent ideal for that size. Book a night from just £50.
  • Need a holiday rental for 8 guests? We have 201 that will suit. Prices begin at just £61 per night.
  • On a trip away with 5 guests? We have 186 holiday rentals that will be perfect. Prices begin at just £52 per night.

You and your crew will be well catered to when you book your Chicago holiday with us!

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