Destination guide

Head to the vibrant city of The Loop

Come and experience The Loop and its architecture, museums and art galleries. Travellers to this cosmopolitan city praise the theatres, entertainment and shopping. For a bit of culture, visit Chicago Cultural Center, Ford Center for the Performing Arts Oriental Theatre or Chicago Theatre. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.


Activities and attractions in The Loop

Do you want to find top things to see and do while you're in the area? Venture out of your cosy holiday rental and check out everything that The Loop has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Skydeck Ledge (0.5 mi / 0.8 km)
  • John G. Shedd Aquarium (1 mi / 1.6 km)
  • Navy Pier (1.2 mi / 1.9 km)
  • Adler Planetarium and Astronomy Museum (1.2 mi / 2 km)
  • Lincoln Park Zoo (2.9 mi / 4.7 km)
  • Brookfield Zoo (11.1 mi / 17.9 km)
Natural features

Exploring the natural landscape of The Loop

Whether you're looking for fun outdoor activities or just want to take in the scenery, The Loop is a great place to get outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (0.3 mi / 0.4 km)
  • Grant Park (0.4 mi / 0.7 km)
  • Lincoln Park (5 mi / 8.1 km)
  • Chicago Riverwalk (0.6 mi / 1 km)
  • Ohio Street Beach (1.2 mi / 2 km)
  • Northerly Island Park (1.3 mi / 2.1 km)
How to get there

Transport options to and around The Loop

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 8.6 mi (13.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Chicago, IL (ORD-O'Hare Intl.), which is 15.9 mi (25.6 km) away.

If you're travelling by train, Chicago Van Buren Street Station, Millennium Station and Chicago Museum Campus-11th Street Station are the main stations that serve the city. It's easy to get around The Loop by jumping on the metro at Adams-Wabash Station, Jackson Station or Harold Washington Library Station.

How many holiday rentals are available around Chicago Loop?

Our 2020 accommodation listings offer a large selection of 249 holiday lettings around Chicago Loop. From 201 flats & apartments to 156 studios, 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 Loop?

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 Loop:

  • Near North Side: 251 holiday homes
  • Bucktown: 63 holiday homes
  • Irving Park: 55 holiday homes
  • Rush & Division: 116 holiday homes
  • West Bucktown: 73 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 Loop? offers a large selection of holiday accommodations near great places in Chicago Loop. From travellers, the most popular points of interest to stay near are:

  • Grant Park: 726 holiday lettings
  • DePaul University-Loop Campus: 1,169 holiday lettings
  • 311 S Wacker Dr: 1,194 holiday lettings
  • Chicago Van Buren Street Station: 1,170 holiday lettings
  • Cadillac Palace Theatre: 1,168 holiday lettings

But there are many other points of interest around Chicago Loop listed on 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 Loop?

Yes, of course. offers 201 Flats in Chicago Loop. Our other popular types of Chicago Loop holiday rentals include:

  • Studios: 156 self catering accommodations
  • Houses: 22 self catering accommodations
  • Townhouses: 6 self catering accommodations

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

Can I find a holiday accommodation with pool in Chicago Loop?

Yes, you can select your preferred holiday accommodation with pool among our 105 holiday homes with pool available in Chicago Loop. Please use our search bar to access the selection of holiday rentals available.

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