Explore Chicago's architectural marvels, a testament to the ambitious spirit of the Prohibition Era, while indulging in its world-renowned cuisine.

You'll start the tour under the dazzling marquee of the Chicago Theater (where you might recognize the neon sign from the movie musical Chicago). You’ll then head towards the Chicago Pedway. This unique feature of Chicago is used by locals and commuters daily to move about the city in a network of underground tunnels. You’ll head back above-ground near City Hall.

Next, you’ll make your way to a spot where you’ll share a sweet treat, and a local tradition: Chicago-style popcorn. Weather permitting, you’ll take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Wrigley Building, and the Chicago Tribune. You’ll end up in the picturesque Millennium Park, home to the iconic Bean sculpture.

Your food tour starts with a very well-known Chicago fare: the Chicago-style hot dog. Every Chicagoan has his or her own preference as to how the dog should be made, and you’ll get a chance to try your guides’ favourite version. Next up is the world-famous Chicago deep-dish pizza. Your guide will take you to a pizza place that’s an icon for Chicago natives to try the real deal for yourself. You'll continue your tasting journey with the Italian beef.

Your tour ends here, and your guide will be happy to direct you back to your accommodation or share tips for what else to do in the city.

Marvel at the stunning Chicago skyline and discover why Chicago’s architecture is among the best in the world
Immerse yourself in the best of Chicago's culture and discover the inspirations that the Prohibition Era had on the city in the 1920s
Enjoy a couple of some classics made-in-Chicago snacks like Chicago-style popcorn and homemade chocolate
Get a taste for Chicago’s most famous food in one of the city’s most historic neighbourhoods
Discover why locals have so much passion for their Chicago-style classics

Important to know

Know in advance:

Note that the Bean sculpture is under construction until Spring 2024 and views will be limited
In the event of a site or road closure, your guide will do their best to take you to alternate locations
Vegetarians and other dietary restrictions can be accommodated. Please notify the provider after booking if you have any dietary requests
This tour runs year-round and will proceed rain or shine unless such weather constitutes a dangerous situation
Please wear weather-appropriate clothing and comfortable walking shoes

Cancellation policy

Receive a 100% refund if you cancel up to 24 hours before the experience begins.

Local English-speaking guide
Transportation between the two tour halves
A variety of food samples (Chicago-style hot dog, deep-dish pizza, and Chicago sandwich, Italian beef, popcorn tasting, chocolate tasting)