Discover a selection of 500 vacation rentals in The Loop, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $70 per night, and condos and studios are popular options for a stay in The Loop. Either way, you'll find a rental for everyone's needs.
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Destination guide

Head to the exciting city of The Loop

Come and experience The Loop and its architecture, museums and art galleries. Travelers to this cosmopolitan city praise the theaters, 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 vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities

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 cozy vacation 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 center:

  • 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 center:

  • 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

Transportation 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 center. 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 traveling 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 vacation rentals are available around The Loop, Chicago?

Our 2020 property listings offer a large selection of 622 vacation rentals around The Loop. From 498 condo and apartment rentals to 516 studio vacation rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to The Loop?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in The Loop:

  • Near North Side: 572 vacation rentals
  • West Town: 527 vacation rentals
  • Lakeview: 233 vacation rentals
  • Lincoln Park: 525 vacation rentals
  • Near South Side: 679 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to The Loop?

Vrbo offers a large selection of vacation rentals near lovely places in The Loop. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Willis Tower: 1,408 vacation rentals
  • Chicago Theatre: 1,406 vacation rentals
  • Millennium Park: 1,034 vacation rentals
  • Chicago Riverwalk: 1,397 vacation rentals
  • Cadillac Palace Theatre: 1,406 vacation rentals

But there are many other points of interest around The Loop listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in The Loop?

Yes, of course. Vrbo has 498 Condos/Apartments in The Loop. Our other popular types of vacation rentals in The Loop include:

  • Studios: 516 rentals available
  • Houses: 40 rentals available
  • Townhouses: 5 rentals available

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

Can I find a vacation rental with pool in The Loop?

Yes, you can select your preferred vacation rental with pool among our 119 vacation rentals with pool available in The Loop. Please use our search bar to access the selection of vacation rentals available.

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