Views of Chicago’s skyline from the water

Chicago Vacations: the Windy City

Chicago is a city of Jazz, Frank Lloyd Wright, and Wrigley Field. From the Art Institute of Chicago, boasting an incredible Impressionist collection, to the architecture along the Chicago River, there’s enough art here to keep the most avid enthusiast busy. Work up an appetite because Chicago is one of the world’s leading culinary cities, with Michelin starred restaurants, deep-dish pizza, and world-famous hot dogs. Whether you’re planning a family vacation to the top of Willis Tower or want to explore Chicago’s luxury restaurants, a Liberty Travel Chicago vacation package can take you there.

Chicago vacations map

Chicago at a Glance

Currency: U.S. Dollar ($)

Tipping Customs: Tip anywhere between 10 – 15%, unless service charge is added

Power Up: Type A or Type B plug, 120 V (the standard in the United States)

Popular Drink: Jeppson’s Malört

Must Eat: Chicago Hot Dog and Deep Dish Pizza

Language: English


Weather: Late spring, summer, and early fall, being warm and mild.

Best Time to Visit: Visit between late May and early October for the best weather.

Chicago Deals

Singer in Chicago at a famous jazz club

Top Things to Do in Chicago

All that Jazz in Chicago
Whether you want to hang in Al Capone’s former haunt at the Green Mill, or are looking for the family-friendly music scene at the Elastic Arts Foundation, Chicago’s musical culture rings with the sounds of Nat King Cole and Louis Armstrong.

Get Inspired by the Impressionists
The Art Institute of Chicago is known for its Impressionist masterpieces, but the collection spans the eras.

Chicago’s Architectural Heritage
Take the Chicago Architectural Foundation River Cruise and afterward, visit the Frank Lloyd Wright Home and Studio to learn about the life and work of this leading architect.

Catch the Cubs at Wrigley Field
Visit the historic ballpark, buy yourself a hot dog, and cheer for the lovable Cubs.

Visit the Willis Tower Observation Deck
The Willis Tower is the tallest building in the western hemisphere; take in the views from the Skydeck.

A saxophone a signature instrument in Chicago’s jazz

Chicago Vacation Packages: Historic America the Liberty Travel Way

Whether you want to visit the Art Institute of Chicago or eat at one of the city’s three-star Michelin restaurants, Liberty Travel’s consultants can create a Chicago vacation package crafted just for you.

When you book with us, you get:

  • Real People. More than a travel agent, your Chicago consultant is a fellow traveler with a passion to help you see the world.
  • Perfect Match. We’ll pair you with a destination expert who has insider knowledge of Chicago for a truly personalized booking experience.
  • Crafted Vacations. Stay in hand-selected hotels. Get connected with local guides and enriching experiences. Choose from among our exclusive Chicago vacation packages, including our CITYbreaks.
  • Support. With 24/7 support, we’ll be with you every step of the way.

We know Chicago. Leave the planning to us.

The Liberty Travel Experience

You are unique, and so is your trip. When you book with Liberty Travel, we match you with an expert best suited to design a vacation just for you.

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