Explore Chicago's history and culture with these top tours this summer

These unique Chicago tours are truly the best way to explore Chicago’s history and culture this summer. 

The First Lady - Chicago Riverboat Architecture Tour

Maybe the most popular and well-known tour the city has to offer, The First Lady has been delivering a best-in-class riverboat experience since its inception nearly 35 years ago in 1991, according to the group's website. Operated by the Chicago Architecture Center, The First Lady puts “architecture first,” leading a rigorous training program for its guides that ensures every guest gets thorough, in-depth, expert information on Chicago’s immense architectural history. 

The boat comes outfitted with indoor and outdoor seating, snacks and beverages available for purchase and bathrooms to make every guest's experience enjoyable and comfortable. The tours typically run around 90-minutes with pick-up and drop-off along the water in the heart of the river north neighborhood. The First Lady Tour has consistently been ranked as one of the best boat tours in the U.S. by publications like USA Weekly and TripAdvisor.

Chicago Gangsters & Ghosts Tour

One of Chicago’s most enduring and tantalizing historical legacies remains its famed ties to organized crime and the prohibition era. So for those interested in taking a walk down the city's macabre past of vice, look no further than The Chicago Gangster and Ghosts Tour. 

Guests are taken to the sites of some of Chicago’s most notorious incidents and criminal hangouts, from the St. Valentine's Massacre to Death Alley, to the haunted Congress Hotel. Immerse yourself in a vibrant criminal underworld while learning about the characters that lived it from trained historian guides. The tour comes in three formats: a walking tour, a minibus tour, and a food tour, all of which last around two hours.

Pizza City Tours

There might be nothing more symbolic of Chicago than our love for pizza of all shapes and sizes. With that in mind, it should come as no surprise that one of the best ways to explore our fine city is through the Pizza City Pizza Tour. 

Owned and operated by renowned culinary journalist Steve Dolinsky, the Pizza City tour takes guests on a mouth-watering journey to four different pizzerias, each showcasing a different type of pie, including tavern style, East Coast-inspired, artisan, and of course, a classic deep dish. Each group is led by an aptly named “Doughcent” with customers offered three different formats: a bus tour, a downtown walking tour, and a West Loop walking tour. 

Dolinsky is a 13-time James Beard Award Winner who has worked as a food reporter for both ABC and NBC Chicago, is a co-host/producer of the Feed Podcast with celebrity chef Rick Bayless, and authored the popular Chicago Pizza guide, “Pizza City, USA.”

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Canine Cruise

For those looking to embark on an adventure with their furry friends, be sure to check out the Canine Cruise. Running from July through October, this pet-friendly riverboat cruise is the first of its kind in Chicago to allow dogs on board the boat. 

Kick back and relax with your pooch as you soak in the sights and architecture along the city's gorgeous riverfront while a guide walks guests through some of Chicago’s most important historical moments. The boat comes outfitted with a full snack and refreshments bar, and yes, there will be plenty of water bowls and treats for all the good boys and girls aboard.

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The Barrel Bus

If you're someone who prefers to get to know a city through its signature libations, then Barrel Run is the tour for you. Guests will board the specially engineered “Barrel Bus” and be taken to a rotating collection of the city's best craft breweries, including Goose Island, Revolution, District Brew Yards & more. 

The company offers public tours as well as private events perfect for occasions such as birthdays, bachelor/bachelorette parties and corporate outings. Private events come with the ability to personalize a route with specific stops and even include a special winery tour option. Each tour lasts around 3.5 hours, includes behind-the-scenes tours of the facilities and brewing process, and comes with 45-55 ounces of complimentary alcohol.