8 Fun and Exciting Chicago Tours

Chicago has pleasant weather during the summer, which is why it’s the perfect season to visit and experience the city’s beautiful sights. One of the best ways to get to know the Windy City is to do a tour—you’ll be able to see the architecture, visit parks and landmarks, taste the unique foods, and experience everything the city has to offer. Chicago has many different tours, from segway to kayak excursions. With so many options it can be difficult to decide which tour to go on, especially if you don’t want to miss out on seeing anything. We’ve compiled a list of some of Chicago’s most fun and exciting tours to help you easily make your decision.

Sightseeing Cruises on Lake Michigan

If you want to glimpse some spectacular views during your trip to Chicago, you’ll want to catch a sightseeing cruise at Navy Pier. While riding on a cruise, you’ll be able to take photos of some of Chicago’s most scenic views while also learning about the history of the city and its famous landmarks. Navy Pier has different sightseeing cruises to choose from including the Seadog Lakefront Speedboat Tour and Seadog Lake Architecture Tour.

Chicago River Architecture Cruise

Climb aboard a state-of-the-art cruise vessel for a 75-minute cruise of all three branches of the Chicago River. You’ll be able to marvel at the architecture that has made the city so legendary while an expert guide shares about some of the city’s history, as well as some of the city’s most renowned landmarks, such as the John Hancock building, Trump Tower, and more. 

Gangsters and Ghosts Walking Tour

Take a 2-hour guided walking tour through the Chicago Loop and discover the stories of gangsters and ghosts from the city’s past. You’ll be able to see the places where gangsters such as Al Capone used to party, make deals, and carry out threats. Additionally, you’ll be able to visit haunted locations and old crime scenes. Some of the places you’ll stop at include the Congress Hotel, Death Alley, and the Palmer House.

Lakefront Segway Tour

Glide around the streets and parks of Chicago on a leisurely 2.5-hour guided Segway tour. You’ll start your Segway experience at Millennium Park and continue to Grant Park where you’ll be able to stop and admire the famous Buckingham Fountain. Ride to Museum Campus to soak up spectacular views of the Chicago skyline and beautiful lakefront. This tour is great for those who are new to Chicago and also those who have been to the city many times.

City Running Tours

These tours are ideal for someone who enjoys running. You’ll be able to start your day with a workout while also touring the city at the same time. City Running Tour is led at a casual pace with designated stops along the way. And don’t worry, it’s designed for runners of all abilities. The Chicago’s Front Yard tour takes runners through Millennium and Grant Park for a fun, social, and educational experience. 

Chicago Underground Donut Tour

If you’re a foodie, then this tour is for you! Some of the stops on this downtown tour include Stan’s Donuts, Do-Rite Donuts, and Firecakes Donuts, true donut institutions. This two-hour walking tour is led by a passionate donut expert who will guide you to some of Chicago’s best donut locales. There are two versions of the Donut Tour: The Classic Downtown Tour, as well as a local neighborhood tour in Wicker Park. Both are great options if you’re excited about donuts. It really just depends on what neighborhood you want to explore: if you want to stay downtown or if you want to venture out to the Wicker Park and Bucktown neighborhoods to see how “the locals do it.” 

Bikes, Bites & Brews: Chicago Biking Tour

Working up an appetite won’t be a problem on this signature tour from Bobby’s Bike Hike Chicago. While on this tour, you’ll have the chance to sample 4 of Chicago’s favorite foods: pizza, hot dogs, cupcakes, and beer. You’ll learn the history behind the iconic foods and also get a taste for some of Chicago’s most popular neighborhoods as you cruise through Wrigleyville, Gold Coast, Old Town, Lakeview, and Lincoln Park. This tour is 13 miles long with breaks along the way for sampling. 

Sunset Paddle Tour on the Chicago River

Kayaking on the Chicago River at sunset is an exciting way to see some of the city’s best architectural features. Enjoy a leisurely pace through Chicago’s magnificent architecture while the changing colors of the sky reflect brilliantly off of the surrounding glassy skyscrapers. This is one of the best ways to experience the city, improve your kayaking skills, and enjoy the friendly fun of paddling with others. Wateriders offers this tour and other kayak tours on the Chicago River, including a History and Architecture Tour and Ghosts and Gangsters Tour.

Planning your trip to Chicago

Whether you choose to visit Chicago now or in the future, you’ll make memories that will last a lifetime, especially if you take one of these superb tours. While planning your trip, you’ll want to select where you’ll stay. Consider booking a hotel located in the heart of the city. You’ll also want to choose a hotel that is fully committed to cleanliness and the health and safety of guests. Remember to bring a mask with you to wear when you are in public spaces, on your tour, or in other areas close to people who are not in your household. Now you’re ready for your upcoming trip to Chicago filled with exciting adventures and stunning sights. 

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