Discover a selection of 249 vacation rentals in Chicago 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 kitchens. Prices start at $80 per night, and condos and studios are popular options for a stay in Chicago 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, HomeAway 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 Chicago Loop, Chicago?

Our 2020 property listings offer a large selection of 249 vacation rentals around Chicago Loop. From 201 condo and apartment rentals to 156 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 Chicago 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 Chicago Loop:

  • Near North Side: 253 vacation rentals
  • Lake View: 204 vacation rentals
  • Lincoln Park: 355 vacation rentals
  • Logan Square: 257 vacation rentals
  • Uptown: 643 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 Chicago Loop?

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

  • Grant Park: 702 vacation rentals
  • Millennium Park: 672 vacation rentals
  • Chicago Theater: 1,116 vacation rentals
  • 311 S Wacker Dr: 1,119 vacation rentals
  • Willis Tower: 1,119 vacation rentals

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

Yes, of course. Vrbo has 201 Condos/Apartments in Chicago Loop. Our other popular types of vacation rentals in Chicago Loop include:

  • Studios: 156 rentals available
  • Houses: 21 rentals available
  • Townhouses: 7 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 Chicago Loop?

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

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