Chicago Attractions: Expert Guide to the Best Tours

Jay Pritzker Pavilion in Millennium Park (Photo: Evgeny Dubinchuk/

Every born and bred Chicagoan knows that the city is full of wonderful nooks and crannies. City native Frank McGehee of Chicago Private Tours is an expert on which landmarks tourists love to visit, like The Magnificent Mile and Millennium Park, but he also knows the places that are often overlooked. McGehee’s intimate custom tours go to beloved and little-known spots, and show off the best of Chi-town’s past and present. Here are his tips for checking out the city with, or without, the help of a tour guide.

Which area of Chicago is underrated?

A lot of people don’t take the time to explore the South Side. Once you start driving through the mansion district, the University of Chicago campus and the Frank Lloyd Wright Robie House, you’ll start looking at all the architecture. Hyde Park is really a jewel on the South Side.

Where in your own neighborhood would you take visitors?

I would take all visitors for a stroll in the Japanese gardens in Jackson Park. It is something that was designed to match the style of gardens that was showcased for the World’s Fair of 1893.

Say a tourist is returning to Chicago again after about 10 years. How has the city changed since then?

Chicago has seen tons of beautification in the past 10 years. A lot of it is thanks to our former first lady of the city, Maggie Daley, who really made it a point to add the flower beds in the middle of Michigan Avenue and Lake Shore Drive. That really beautifies the city with living, breathing art.

What is the best way to travel around the city to see the sights?

I recommend the bike sharing programs to get people out there on their bikes and check out the city. It’s really more of an active city now and I think that’s something to be appreciated.

Our tours offer a vehicle, so we can get you all the way up to the North and South Side, but we try to get out of the vehicle as much as possible so we can look at the architecture in greater detail. At the end of the day, you need to get out and look at the building. Just look up and realize how beautiful the city of Chicago is.

What is the coolest thing that’s happened to you while giving a tour?

One client had us customize the tour to go by all the places where the couple had great memories, but to act like it was just part of the tour. At the end, he proposed and just as she said yes the fireworks at Navy Pier started going off, making it a perfect night for them.