A Different Way to Experience Chicago

The sculpture looms over Millenium Park – a popular spot for al fresco dining
The sculpture looms over Millenium Park – a popular spot for al fresco dining | | © Jeffrey Isaac Greenberg 2 / Alamy Stock Photo
Culture Trip Travel Team

With so many sky-high sights and so much to do, it can be hard to get a handle on Chicago. These handpicked tours and experiences take you away from the crowds and give you a fresh, hands-on take of Chicago.

Chicago has certain must-dos on every visitor’s checklist: try deep dish, visit Chinatown, learn the history and give a hearty “Oooh!” at the designer skyscrapers. But ticking those off away from teeming crowds and with local, experienced guides is one of the most fun ways to get a fresh look at the city. Don’t just eat deep dish – make one! Why settle for just history or just architecture when your tour can have both – plus bites! Discover secrets and go behind the velvet curtain (sometimes literally, at the Chicago Theatre) to get truly unforgettable insights into the real Chicago.

1. Chicago Pizza Tour


Enjoy Chicago’s only bus-guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza. Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias. In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.

2. Chicago Loop Secret Food Tour


Join this 3-hour tour of Chicago’s food scene, and see what sets this friendly Midwestern metropolis apart. On this 12-person-maximum walking tour of the ‘Chicago Loop’, a local guide will share with you some hidden gems and great stories about the city. Taste where the world-famous dipped Italian beef sandwich was invented, try some of the best deep dish Chicago pizza. Be shown how important the immigrants that built this town are to the food scene.

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