Bring your appetite when you travel to Chicago — not just for food, but also for design, culture, architecture, and adventure. Dive into everything the Windy City has to offer, like stand-up paddleboarding in Lake Michigan, cheering on the Chicago Cubs at Wrigley Field, exploring the city’s endless art galleries and museums, and strolling the gardens at Millennium Park. Need a shopping fix? Take a weekend getaway and browse through the luxury brands lining the Magnificent Mile and the boutiques of River North. No visit to Chicago is complete without taking an architecture cruise on the Chicago River or devouring the city’s eclectic and classic eats. A slice of deep-dish pizza, anyone? Between the trendy cocktails in Logan Square and the Centennial Wheel at Navy Pier, you’ll find what will make your Chicago vacation so much better — Chicago vacation homes and hotels that put you right in the middle of the action, like cosmopolitan hotel suites and penthouses on the Gold Coast. Prefer nature and trees over city skyscrapers? Cozy log cabin rentals await in nearby state parks.

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Looking for a vacation rental near a particular attraction, famous landmark, or another point of interest? Use this map of Chicago to help guide your rental search.

Chicago travel guide

Let us help you plan your perfect Chicago vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Chicago, and more.

Nearby attractions

Frequently asked questions

What are the most popular vacation rental amenities in Chicago?

  • Internet / Wifi
  • Air Conditioner
  • TV

What are the top attractions in Chicago?

Chicago has plenty of top attractions, making it one of the most dynamic cities in the world. Some of these attractions include:
  • - Millenium Park
  • - Chicago Riverwalk
  • - Navy Pier
  • - Lake Michigan Lakefront Trail
  • - Willis Tower
  • - 360 Chicago
  • - Michigan Avenue and Magnificent Mile
  • - Wrigley Field
  • - Lincoln Park
  • - Second City Comedy Club
  • - Cloud Gate

Is Chicago a good place for a family vacation?

Yes, Chicago is a great place for a family vacation. Your whole family will fall in love with Chicago’s unique attractions and experiences, such as:
  • - Scoping out the view at the Willis Tower Skydeck
  • - Riding the Centennial Wheel at Navy Pier
  • - Taking a boat or kayak tour on the Chicago River
  • - Catching a game at Wrigley Field
  • - Exploring the Museum of Science and Industry
  • - Getting lost in the Chicago Children’s Museum

When is the best time of year to visit Chicago?

The best time of year to visit Chicago is late spring between April to May and fall in September or October, when you’ll experience pleasant temperatures, fewer crowds, and some of Chicago’s most popular events — including the Hyde Park Jazz Festival, baseball home opener games, and Chicago Restaurant Week.

What is the Chicago Loop?

Exploring the Loop on foot is a can't-miss activity when visiting Chicago. Enjoy historical buildings, shopping, art galleries, and delicious food. Put the iconic Bean in Millennium Park on your list, and swing through the Theater District as well.

What is the Humboldt Park area in Chicago known for?

The Spanish Colonial architecture in Humboldt Park helps create a distinctively Latin aura. This is even more evident in the specialty shopping and cuisine.

What is the Lakeview area in Chicago known for?

Lakeview is a thriving lakefront community with a wide array of attractions. Street festivals are popular during the summer, and acres of green space offer breathtaking beauty.

How many rentals are available in Chicago?

There are 2,628 vacation rentals available in Chicago across several booking partners.

What is the price range for rentals in Chicago?

Vacation rentals in Chicago have a price range between $39-$2,997. The average price for rentals in Chicago is $119 per night.

Chicago travel inspiration

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