The Best Chicago Tours

Wondering what to do with your out-of-town visitors this Memorial Day weekend? Or want to play tourist yourself? Book a tour and learn about Chicago food, architecture, and more.

Chicago Architecture Center River Cruise

You can’t really go wrong with any of the river cruises, but this 90-minute ride on Chicago’s First Lady has gotten many accolades over the years for good reason. Known as one of the more educational river cruises, guides know their stuff.

Chicago Mahogany Tours

Historian Shermann “Dilla” Thomas isn’t just teaching people about the greatest city in the world on TikTok — he’s also giving bus tours IRL. Join him in learning about Bronzeville, Englewood, North Lawndale, Pilsen, Little Village, and more.

Tours With Mike

If you are looking for something unique, Mike McMains is your guy. His tours range from ugly buildings to underground rats to LGBTQ stories. Plus, he’s an expert on how YOU can be the best Chicago host for your guests.

Chicago Greeter

This free tour offered through Choose Chicago is best for visitors who want to explore outside of downtown. Neighborhood pop-up walks are offered on Saturdays.

Inside Chicago: Pedway Tour

Exploring the city’s underground tunnels can be intimidating for anyone. But if you are hoping to use the Pedway to get around, consider going with a tour guide first. Walk past underground pools, stained glass, and more.

Bobby’s Bike Hike

This tour company offers biking, walking, and food tours across Chicago. I just took some family on this Chinatown food tour where we sampled different regional cuisines. I’m still thinking of the dim sum 🤤

Read & Run Chicago

Whether you want to go on a running tour, trail run, or book club run, this group does it all. Plus, Read & Run is starting chapters in other cities. If you’re in San Diego or Los Angeles in the next few weeks, you can join runs in California.

The Barrel Run Brewery Tour

Calling Chicago beer lovers: Hop aboard the Barrel Bus to learn about and visit breweries like Lake Effect, Revolution, Goose Island, Burning Bush, Pilot Project, On Tour, and Great Central.