One of the best ways to sightsee your way through a new city is with the help of a local. With this in mind, NatureGuide rounded up some of Chicago’s best guided tours. Whether you’re sailing past Willis Tower on a river cruise or sampling some of Chicago’s best deep-dish pizza on a foodie excursion, you’ll gain a cultural and historical understanding of the Windy City during these tours.
Price: Adults from $44; kids from $20
Duration: 1.5 hours
NatureGuide independently paid to send Cortney Fries, an award-winning writer based in Chicago, on this tour to provide readers with an unbiased, first-hand perspective of what to expect. The Wendella Boats Chicago River Architecture Tour was selected by our team as a Best Overall pick thanks to its popularity and favorable user reviews.
Cruise three branches of the Chicago River taking in views of famous Chicago landmarks while a knowledgeable guide provides an overview of the architecture and interesting lessons in Chicago history on this popular boat tour. For instance, did you know that the Lyric Opera House was built in the shape of a giant throne? Learn how the Chicago River is the only natural river reversed by humankind. View iconic buildings, such as the Merchandise Mart and Willis Tower. Hear about what the four stars on the Chicago flag represent, the legend of the O’Leary cow starting the Great Chicago Fire, the statue atop the Chicago Board of Trade and Chicago’s famous drawbridges.
Refreshments and snacks are sold on board. Sit on the top deck to listen to the live tour with unobstructed views, but bring a jacket or sun hat if it’s cool or sunny. Climate-controlled seating is offered below, as are restrooms. Tours are generally available daily beginning at 9:30 a.m., with multiple departures throughout the day and evening. Short on time, or have kids in tow? Try the 45-minute version of this architecture tour.
Why we love it:
- Learn about the dense variety of architectural styles along the Chicago River without having to navigate crowded streets.
- Engaging guides make for a memorable experience and provide glimpses into different parts of the city you might want to explore more during your trip.
- Tours depart from Michigan Avenue near the Wrigley Building. Give yourself plenty of time to find parking and also enjoy ample shopping and dining options nearby.
Price: Adults from $85; kids from $50
Duration: 3 hours
This foodie tour centers on the West Loop neighborhood’s incredible dining scene, and provides insider insights to the area’s evolution from a meat-packing and warehouse district to the Restaurant Row of today. Foods you may sample include doughnuts, hamburgers, pizza and cupcakes. Guides regularly earn five stars from travelers for their insight and enthusiasm. Reviewers find the tour worth the price for the generous amounts of food provided. What’s more, group sizes are restricted to 16 people and tours do not involve extensive walking (a little more than half a mile).
Tours are offered Sunday, Thursday and Friday at 1 p.m., though availability may be more limited in the winter months. Hungry for more? The company also offers a tour inspired by the TV show “The Bear,” which is set in Chicago, as well as a tour all about the city’s most iconic foods.
Price: From $65
Duration: 2 hours
The Chicago Lakefront/Museum Campus tour offered by Absolutely Chicago Segway Tours showcases many of the city’s most popular attractions along its 5- to 6-mile route, including Millennium Park (the starting point), Grant Park, Monroe Harbor, the Field Museum, Shedd Aquarium, Soldier Field and the Adler Planetarium. Participants applaud tour guides for their expertise and professionalism and say this is a safe, fun way to see the city’s top sights in a short amount of time.
Note that riders must be at least 12 years old to participate. Tours are available multiple times a day from spring through autumn. The company offers several other Segway tours, some centered around other parts of the city or with specific themes like architecture, crime and ghosts.
Price: Adults from $30; kids from $25
Duration: 2 hours
Many travelers are familiar with Chicago’s distinct architecture, but its equally captivating indoor spaces are not as well known. This tour reveals interior architectural details that visitors might otherwise miss. Guides take participants inside some of Chicago’s most stunning buildings to admire elements like a gilded 80-foot-high ceiling, art deco lobbies, early Frank Lloyd Wright designs and rooms with stained-glass mosaics. Reviewers describe this tour, which requires about 1.5 miles of walking, as an informative and entertaining way to learn about the history of Chicago and its diverse, distinctive buildings. Others said this tour is great for first-time visitors and locals alike.
Tours operate Thursday through Monday at 11 a.m. Once you’ve toured all of the buildings at the street level, consider the company’s Chicago Pedway tour, which tours the downtown underground tunnels that residents use to stay warm and dry during bad weather.
Price: From $85
Duration: 4.5 hours
This triple-threat tour combines bicycling, food and beer. The 13-mile ride traverses the Gold Coast, Lakeview, Wrigleyville and Lincoln Park neighborhoods with stops for pizza, beer, cupcakes and hot dogs. Reviewers say the pace of the tour is easy and applaud the guides for their fun and engaging commentary. Others said they learned a lot about Chicago, calling the ride entertaining and educational.
Tours are generally offered daily at 11:30 a.m. and 5:30 p.m. (except during the winter). Note that the evening tour mostly bikes around downtown Chicago. If you’re interested in venturing beyond downtown, book the morning tour. Tickets cover the cost of the bike rental as well as food and drinks. Participants must be at least 21 years old. If you’re traveling with kids, try the company’s Family & Food Bike Tour of Top Attractions.
Price: Adults from $35; kids from $17
Duration: 2 hours
If you’re interested in the darker side of Chicago history, specifically its gangsters and ghosts, consider this walking tour. With a historian leading the way, you’ll stroll for about 1.5 miles around the Loop – once known as the “Vice” district in the 1920s and ’30s for its rampant partying, speakeasy saloons and underground tunnels used by bootleggers. Participants rave about the guides for their storytelling abilities and say the length of the tour is perfect for when you need a break from the city’s more touristy activities. Reviewers also appreciate the emphasis on historical facts, and say the tour is family friendly.
Tours run four times daily beginning at 11 a.m. The company also operates a Gangster Food Tour that highlights some of the city’s most iconic foods like deep-dish pizza and hot dogs, as well as the restaurants that once served as some of Al Capone’s old hideouts.
Price: Adults from $49.50; kids from $35.10
Duration: 2 hours
Big Bus Chicago’s hop-on, hop-off tours invite tourists to tailor their sightseeing excursions to their preferences by allowing them to spend as much time as they want at any of the 11 stops on the company’s red route. Tour-takers can “hop off” a bus and explore any of the top attractions featured along the way, such as Skydeck Chicago, Navy Pier or Millennium Park, and then “hop on” a later bus. If you don’t get off the bus, the entire route takes about two hours. Your ticket is valid for 24 hours, so you can hop on and off as much you please. Buses run every 30 minutes starting at 10 a.m. daily and include prerecorded commentary in both English and Spanish.
Reviews from recent travelers were mixed: Some riders appreciated the convenience of the bus, saying it puts you within easy walking distance of the city’s best attractions and allows you to cover a lot of ground in a short amount of time. Others were disappointed with the quality of the prerecorded commentary, calling parts of it cheesy, and said you should try to seek out the few buses that feature live commentary from the driver.
Price: Adults from $65; kids from $55
Duration: 2 hours
Come hungry for this food tour, which visits four of the best doughnut shops in the city, including Doughnut Vault and Do-Rite Donuts. As you nosh on the sweet treats, your guide will share the history of each shop and the history of doughnuts in Chicago. Travelers recommend this tour for the knowledgeable, engaging guides and the delicious selection of doughnuts. They also say you’ll learn about much more than doughnuts, as guides share historical tidbits about Chicago and recommendations for how to make the most of your trip.
Tours operate daily at 10 a.m.; additional 9 a.m. and noon tours are offered Wednesday through Saturday.
Price: From $60
Duration: 2 hours
For a “duck’s-eye” view of the city, take Urban Kayak’s Historic Chicago Tour. Starting at the Riverwalk, tour-takers paddle their kayaks on the main branch of the Chicago River with periodic stops at points of historical interest, where guides provide information regarding the city’s famed architecture. Reviewers say this is a great experience, even for beginners, and recommend the tour for travelers looking for a unique alternative to the popular architecture river cruises. Meanwhile, others note that the experienced guides are skillful at navigating boat traffic.
Price: Adults from $30; kids from $12
Duration: 45 minutes
If you’ve already taken an architecture cruise on the Chicago River and can’t get enough of the views, consider this boat tour. Shoreline Sightseeing Skyline Lake Tours offer unrivaled views of Chicago’s skyline, and many photo opportunities, via cruises along the Lake Michigan shoreline. The 6-mile trip provides views of notable landmarks, such as the John Hancock Center, the Willis Tower (aka the Sears Tower), Adler Planetarium and the Field Museum, as well as an informative prerecorded audio commentary. According to reviewers, these iconic buildings are much more visible from the water than they are on the street, though a few warned that it’s difficult to hear the recorded commentary from certain areas of the boat (sit in the middle of the boat if you want to ensure you can hear the narration).
Travelers can purchase drinks at the onboard cash bar. Tours are offered daily spring through autumn (weather permitting) and depart from Navy Pier. Shoreline Sightseeing also offers architecture cruises along the Chicago River.
Hi, this is a comment.
To get started with moderating, editing, and deleting comments, please visit the Comments screen in the dashboard.
Commenter avatars come from Gravatar.