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Chicago Vacations:
the Windy City
Depart from the Windy City — or Explore It Like Never Before
As a Chicago-based travel agency, Vacayzing helps locals and visitors plan unforgettable vacations — whether you're flying out to paradise or staying right here in the city we love.
Want to escape the cold with a luxury beach getaway? Or book the perfect family trip from Chicago to Cancun, Paris, or Punta Cana? We’ll handle every detail, from flights out of O’Hare and Midway to resort packages, cruises, and honeymoons.
Prefer to stay local? Let us show you a new side of Chicago. We can help you plan the perfect staycation — from world-class hotels and dinner cruises to tickets for the Art Institute, Wrigley Field, and skyline helicopter tours.
Whether you're leaving or staying, Vacayzing is your go-to travel partner in the Windy City.
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.
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.
