Note: Some tour providers on this list may have limited or ceased operations due to COVID-19. Check with your tour operator about availability before you book.
One of the best ways to sightsee your way through a new city is with the help of a local. With this in mind, U.S. News rounded up 14 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.
Chicago Food Planet – Gateway to the West Loop Food Tour
Chicago Food Planet’s Gateway to the West Loop spotlights some of the tastiest dishes in the city – specifically pizza, doughnuts and burgers. The three-hour tour centers on the West Loop neighborhood’s incredible food scene and provides insider insights to the history and culture of the area. Guides regularly win praise from travelers for their knowledge and enthusiasm. Ticket prices start at $65 for adults and $50 for children ages 12 and younger. Reviewers find the tour worth the price for the generous amounts of food provided. What’s more, group sizes are restricted to 14 people and tours do not involve extensive walking. Tours are offered Thursday through Sunday at 1 p.m. Chicago Food Planet also offers tours of Chicago’s Chinatown neighborhood.
Absolutely Chicago Segway Tours – Chicago Lakefront/Museum Campus
The Chicago Lakefront/Museum Campus tour offered by Absolutely Chicago Segway Tours showcases many of the city’s most popular attractions, including Millennium Park (the starting point), Grant Park, Monroe Harbor, the Field Museum, Shedd Aquarium, Soldier Field and the Adler Planetarium. The 8-mile journey on easy-to-ride, two-wheeled, battery-powered vehicles lasts approximately 2 1/2 hours. Participants praise tour guides for their insight and professionalism. Tickets cost approximately $65, depending on date and time. Note that riders must be at least 12 years old. Tours are available daily. The company offers several other tours, some centered around other parts of the city or with specific themes like architecture, crime and ghosts.
Inside Chicago Walking Tours – Dazzling Interiors of the Loop
Inside Chicago Walking Tours’ The World Within: Dazzling Interiors of the Loop tour reveals interior architectural details that visitors might otherwise miss. Highlights of the two-hour tour include 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 involves about 1 1/2 miles of walking, as an informative and entertaining way to learn about the history of Chicago and its diverse, distinctive buildings. Tickets start at $30 for participants 11 and older and $25 for children ages 5 to 10 and patrons 65 and older. Children ages 4 and younger tour for free. Outings run Saturdays at 11 a.m. Inside Chicago also offers other architecture-oriented tours as well as private tours.
Bobby’s Bike Hike offers several different tours, including a 13-mile Bikes, Bites & Brews tour.(Courtesy of Bobby’s Bike Hike Chicago)
Bobby’s Bike Hike Chicago – Bikes, Bites & Brews Tour – Signature Dishes
This triple threat tour combines bicycling, food and beer. The four-hour, 13-mile ride traverses the Gold Coast, Lakeview, Wrigleyville and Lincoln Park neighborhoods with stops for pizza, beer, cupcakes and hot dogs. Reviewers find the tour provides a great introduction to the city and rate the guides highly. Tickets for adults, which include the bike rental as well as food and drinks, start at $76.99 for weekday rides (weekend rides are slightly more expensive). Participants must be at least 21 years old. If you’re traveling with kids, try Bobby’s Bike Hike Chicago’s Family Food & Bike Tour.
Chicago Pizza Tours – Original Chicago Pizza Tour
Experience one of Chicago’s unique culinary phenomena with the Original Chicago Pizza Tour. On this 3 1/2-hour tour, you’ll visit four independently run neighborhood pizzerias and sample six or more slices. Many reviewers praise the informative and entertaining tour guides. Others insist that the tour is about more than just pizza and encompasses Chicago history, architecture and culture. Tickets start at $60 for adults and $36 for children. If you’re interested in exploring the city’s pizza from other angles, you can take one of the company’s other food tours, which combine pizza and cocktails or focus on the city’s biggest slices.
Big Bus Chicago’s tours give tourists the opportunity to see Chicago’s sites at their leisure.(Courtesy of Big Bus Chicago)
Big Bus Chicago Hop-On Hop-Off Tour
Big Bus Chicago’s Hop-On Hop-Off Tours permit guests to tailor excursions to their preferences by allowing them to spend as much time as they want at any of the 12 stops within the eight hours of the standard package. Tour-takers can “hop off” a bus and spend time at popular destinations like Skydeck Chicago, Navy Pier, Soldier Field or Millennium Park and then “hop on” a later bus. Buses run every 30 to 45 minutes and include guides that provide commentary. Travelers frequently describe guides as entertaining and informative. One pain point for riders is the signage: some found it difficult to locate the bus stops at certain attractions. Ticket prices start at $49 for adults and $30 for children (though you may be able to score a discount by purchasing online in advance). In addition to its classic ticket, Big Bus Chicago offers a premium ticket valid for two days.
Tastebud Tours – Taste of Chicago
Tastebud Tours’ Taste of Chicago explores the city’s downtown Loop area. The three-hour tour includes stops at multiple restaurants and shops for distinctive Chicago deep-dish pizza, popcorn, sandwiches and sweets. The tour also highlights non-food-related landmarks like the Chicago Cultural Center, the Art Institute of Chicago and the Marshall Field and Company Building, which visitors tend to appreciate. Guides consistently win praise for their knowledge of and enthusiasm for Chicago history. Tickets, which start at $59.50, include all food. (Adult beverages can be purchased separately where available.) Groups are limited to 18 people. Tastebud Tours also offers other food-centric excursions as well as private tours.
Chicago Architecture Foundation River Cruise
The Chicago Architecture Foundation’s River Cruise ferries guests along the Chicago River as docents from the Chicago Architecture Center regale them with the stories behind more than 50 notable buildings. The volunteer docents repeatedly win high praise from reviewers for their in-depth knowledge of the city’s history and its structures. The cruising vessels, part of the Chicago’s First Lady Cruises fleet, can carry up to 250 people and boast full-service bars and open-air upper decks. Tickets for the 90-minute excursions cost around $45 for daytime cruises. Twilight outings are a few dollars more. For an additional $5, you can also gain admittance to the Chicago Architecture Center (which usually costs $12 on its own).
Guides on Chicago Prohibition Tours can offer travelers suggestions on Prohibition-inspired drinks to order(Courtesy of Chicago Prohibition Tours)
Chicago Prohibition Tour – Original
Chicago Prohibition Tours explore a notoriously eventful moment in the city’s history. Its flagship offering visits the sites of four former speakeasies via bus over the course of 3 1/2 hours. Guides provide historical information and share what kinds of drinks would be representative of those consumed illicitly during the Prohibition era. Additionally, you will be driven from location to location by the company. Reviewers rave about the fast-talking guide and say this is an experience both locals and visitors will enjoy. Others appreciate that each bar on the tour is unique. Tickets, which start at $55, do not include food or drinks, which can be ordered separately at tour-takers’ discretion. There is also a walking version of this tour that lasts 2 1/2 hours.
Urban Kayak Chicago Riverwalk – Historic Chicago Tour
For a “duck’s-eye,” up-close 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. Meanwhile, others note that the experienced guides are skillful at navigating boat traffic. Tickets cost approximately $65 for a single kayak or $130 for a tandem (two-person) kayak for the approximately two-hour tour. Urban Kayak also offers kayak rentals and paddleboarding classes.
Shoreline Sightseeing – Skyline Lake Tours
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. According to reviewers, these iconic buildings are much more visible from the water than they are on the street. Many say this tour was the highlight of their Chicago trip. Tickets for the 40-minute, narrated boat rides start at $23 for adults and $8 for children ages 3 to 12. Kids 2 and younger ride free. Travelers can purchase drinks at the onboard cash bar. Shoreline Sightseeing also offers architecture-focused tours along the Chicago River.
The Tall Ship Windy provides tourists an enjoyable sailing and sightseeing experience.(Ken Flisek/Courtesy of Tall Ship Windy)
Tall Ship Windy – Chicago Skyline Sail
Tall Ship Windy’s Chicago Skyline Sail features views of the city from the deck of a 148-foot, four-masted schooner. Reviewers tout the remarkable views of the city’s impressive structures and, weather-permitting, the special experience of being able to actually sail and not rely on the boat’s motor. What’s more, tour participants commend the crew members for their professionalism. Tickets for the summer and fall excursions start at $37 for adults and $17 for children ages 12 and younger; infants 12 months and younger ride for $1. Tall Ship Windy has a full bar on board (drinks are not included in the ticket price.) In addition to the daily 75-minute excursions, Tall Ship Windy offers fireworks cruises on select dates as well as pirate-themed outings.
Chicago Crime Tours explore famous crime scenes in a variety of Chicago neighborhoods, including the Gold Coast, Lincoln Park, the Loop, the Magnificent Mile, Old Town and River North. The bus tour, which lasts about two hours, includes stops at the spots where gangsters like Hymie Weiss were killed as well as the site of the St. Valentine’s Day Massacre. It also visits locales associated with Al Capone, Frank “the Enforcer” Nitti and Leopold and Loeb, among others. Reviewers laud the tours for providing a unique angle on Chicago’s colorful history. Tickets cost approximately $40 and can be purchased in advance (advised) or on the bus. A nighttime crime tour and a pizza and crime walking tour are also available.
City Cruises by Hornblower – Seadog Lakefront Speedboat Tour
Zip across Lake Michigan during this high-speed, musically enhanced 30-minute tour. During the ride, you’ll see striking views of the Chicago skyline and hear some descriptions of the sights. Visitors praise the crew’s knowledge and charisma. They also enjoy whipping along the waves. Tickets cost about $30 for adults and $20 for kids ages 3 to 12. Children ages 2 and younger ride free, but do require a ticket. The boat is open-air, which means travelers might get wet. City Cruises runs a myriad of other boating adventures, including an extreme thrill ride.
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