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

Consultant Cards Block
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

Our Commitment to You

For over 70 years, the one-on-one personal experience has been at the very heart of Liberty Travel’s mission. It's what we've always done, and now it’s more important than ever.

We’re committed to serving you through:

  • GUIDANCE with our expert insight and travel knowledge.
  • VALUE with irresistible rates, offers and benefits.
  • PEACE OF MIND to book with confidence.
  • SERVICE by being by your side before, during, and after your trip.

Real people helping real people. Beside you every step of the way.

The Liberty Travel Experience

At Liberty Travel it’s the people who make a difference. Our travel experts craft the perfect trip for every traveler through our award-winning customer service. Real people helping real people. Beside you every step of the way.

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