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Chicago Travel Guide

One of the largest cities in the US has reinvented itself into a hub of art, music, food, and culture. Keep reading as we take you on a journey through Chicago.

The Windy City Reinvented

It’s home to more than 250 theatres, 225 music venues and 125 art galleries; with new food and drink spots opening daily. No surprise then that America’s windy city was named the “world’s most popular city” for the 2nd year in a row by Timeout magazines City Life Index 2018.

Once known more for its crime rate than its culinary scene, Chicago has increasingly captured the hearts of business and leisure travellers alike.

Last year Mayor Rahm Emanuel announced that the city hit its record high in terms of visitor numbers – 55.2 million, which was an increase of 2.5% on the previous year’s record high.

The city, affectionately known to locals as “Chi” (yes, Chicagoans came up with this nickname way before Kim and Kanye!), reported an all-time record high attendance for many of the conventions and business meetings held in the city. In addition, hotels reported an annual increase of 6.3% in occupancy rates in 2017 - contributing to the overall growth in travellers last year.

The well-earned title of “world’s most popular city” has travellers flocking to Chicago to enjoy the best of what the city has to offer; and there’s a lot.

More than 100 art deco, contemporary and cutting-edge skyscrapers fill the Chicago skyline; from the historic John Hancock Center and neo-gothic Tribute Tower to the new-age Aqua building, reminiscent of a waterfall.

With the variety of architecture and design, these giants of the sky are almost as diverse as the people of Chicago. A truly multicultural city, travellers can explore different art, food and culture in places like Chinatown, the Ukrainian Village and Greektown. To pay homage to their Irish- Chicagoans, every year on St Patrick’s Day they even dye the Chicago River green!

What’s more, the city hosts a pizza party every February, and was voted the best place to eat and drink in the world by Timeout Magazine.

The Windy City Reinvented

Your Chicago Bucket List

With so much to do and see, we’ve put together a list of both popular attractions and unique experiences to add to your Chicago bucket list.

Popular Attractions

  • Enjoy a free concert or art installation at Millennium Park.
  • Watch the Cubs play baseball, or take a tour of the famous Wrigley Field.
  • Marvel at the largest Tyrannosaurus rex skeleton ever found, or hang out with the mummies of Egypt at the Field Museum.
  • Catch a comedy or improv show at the Second City – famous for launching the careers of comedians like Tina Fey and Bill Murray.
  • Check out the views from the Willis Tower Skydeck or Chicago 360.
  • Channel your inner Bill Nighy the Science Guy as you create your own tornado or rainbow at the Museum of Science and Industry.

Unique Experiences

  • Sip on a craft beer at one of Chicago’s many beer destinations, such as Haymarket Pub, Forbidden Root Restaurant & Brewery and the world’s first Michelin-starred brewpub, Band of Bohemia.
  • Take part in one of Airbnb’s experiences including glass-blowing, watercolour sketching or coffee painting classes.
  • Take in the beauty of Lake Michigan as you run along the Lakefront Trail.
  • Pick up some local produce at the Logan Square Farmers Market.
  • Listen to some Jazz or poetry at Al Capone's old haunt, the Green Mill Lounge.
  • Take a free tour of the “chapel in the sky” – the world’s tallest church Chicago Temple.
  • Visit Grant Park in Chicago to see where the historic route 66 starts.

Who’ll Love the Windy City?

  • Architecture aficionados
  • Baseball fans
  • Foodies
  • Museum lovers
  • Fans of craft beer


Key Facts:

Population: Approx. 2.7 Million

Location: Sits on Lake Michigan in the US state of Illinois

Currency: US Dollars

Best Time to Travel: Peak season in Chicago runs from June to August. This means warmer weather and more going on, however it also means higher prices and more travellers. April, May, September and October are good times to visit as you’ll avoid not only the crowds but also the sub-zero winters. Travel in November to March and you’ll get some great deals as most travellers can’t hack the average temp of -1 degree!

Inspired to travel to Chicago? Buy your USD before you get there, or sign up to track USD rates so you’ll know when it’s a good time to buy.