Guided tours of Chicago

April 19, 2019 by MrEricSir

In Chicago I took a few tours that were highly recommended online. There’s something said for the wisdom of the crowds, these are all solid tours I enjoyed and would recommend as well if the subject matter interests you.

 
Lou Malnati's deep dish pizza
 

Second City Classic Food Tour from Chicago Food Planet

My first tour in Chicago was this “classic” food tour which focuses on various cuisines you can readily find in Chicago. I don’t think it’s a spoiler to say that yes, Chicago deep dish pizza is included — and it’s the first stop.

I’ve had deep dish pizza before (I mean, who hasn’t?) but this one was above and beyond anything I’d ever tried. As the only non-meat eater in the group I got a small pizza all to myself instead of “just” a big slice with sausage. Even though I arrived hungry I couldn’t finish the entire thing, it was too big and too rich. The most amazing part wasn’t the crust or the cheese — it was the crushed sweet tomatoes on top instead of a traditional sauce. Everyone had the same tomato topping.

The other stops on the tour included a mix of local and international food, beverages, ingredients, and a classic local bar and BBQ joint. Since I don’t eat meat I can only vouch for the homemade BBQ sauce.

The architectural component of the tour was cut short because, well, it was snowing. On the bright side we also had a more intimate experience due to several last minute cancellations.

Book this tour on their website.

 
Chicago "Corncobs"
 

Chicago Architecture Cruise from Chicago Line Cruises

With many architecture cruises and walks to choose from, I went with this one not only because of recommendations, but because it’s the most comprehensive.

The tricky part is figuring out where this tour starts; you’ll probably pass by similar tours on the way there. Just keep an eye out for the cruise company logo and take your phone’s directions with a grain of salt — location services can be a little wonky with tall steel structures around you.

The tour guide lectures at a fast pace on the architecture along the Chicago river. You’ll learn how architects think about integrating buildings into their surrounding environment as well as how they work around the unique challenges of building on the river, and in some cases the existing rail infrastructure underneath the new structures.

Another common theme is how modern developers adapt and reuse existing buildings that were originally built for, say, a Montgomery Ward order fulfillment warehouse.

Complimentary soft beverages, coffee, and snacks are available on the lower deck. Beer and wine are available for an extra charge.

Dress warm for this one, the Chicago river is significantly cooler than the city above.

Book this cruise on their website.

 
Congress Hotel
 

Gangsters and Ghosts Tour

If you keep up with the news at all it’s no secret that Chicago has a problem with violent crime. (Side note: crime isn’t a major concern for most tourists.) This walking tour focuses on Chicago’s dark past as well as places that are allegedly still haunted by it.

Without spoiling anything major, here are a few key points of the tour:

  • The life and death of notorious mob boss Al Capone
  • A mass tragedy that led to certain modern day fire codes
  • How the mafia used Chicago’s infrastructure to hide the sound of gunshots
  • The story of America’s first serial killer

It’s a fairly long tour; about two hours with a lot of walking and some stairs. There’s a bathroom break partway through so I’d recommend bringing water. The guide didn’t pull out any gory photos or anything though the descriptions were graphic enough that the younger or more squeamish guests might want to steer clear.

Book this one through their official website or on Airbnb Experiences — the price is the same either way.

 
Pedway tour
 

Discover Chicago’s underground city

Did you know Chicago has series of ad-hoc underground public walkways known as the “pedway”? This hour long tour takes you through a few of them, connecting government buildings, malls, three train stations, and more.

It’s the perfect indoor walking tour for a day when the weather’s not so great. The tunnels aren’t at a consistent level and some are better cared for than others. Weirder yet, not all of them even appear on any (semi) official map.

It’d be super easy for us tourists to get lost down there without a guided tour. Fortunately the tour guide, Margaret, is an incredibly warm and passionate person who knows her way around and loves sharing her knowledge.

This one an only be booked only through Airbnb Experiences.