The 15 Best Chicago Tours

Foodies, boat enthusiasts and historians alike will appreciate any one of these tours of the Windy City.

U.S. News & World Report

The 15 Best Chicago Tours

Best Chicago Tour

Chicago Food Planet's food tours let you taste iconic Chicago cuisine.(Courtesy of Chicago Food Planet)

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 15 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 city during these tours.

Chicago Food Planet - Best in Chow Food Tour

Chicago Food Planet's Best in Chow Food Tour spotlights multiple dishes associated with the city – specifically deep-dish pizza, hot dogs, Italian beef sandwiches, brownies and popcorn. The three-hour tour centers on the River North and Streeterville neighborhoods and provides insider insights to the history, architecture and culture of these areas. Guides regularly win praise from travelers for their knowledge and enthusiasm. Ticket prices start at $60 for adults (or $80 for a VIP package, which includes three drinks) and $35 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 16 people and tours do not involve extensive walking. Chicago Food Planet also offers tours of other neighborhoods, including Chinatown and the West Loop.

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 knowledge and professionalism. Tickets cost approximately $65, depending on date and time. Note that riders must be at least 12 years old. Absolutely Chicago Segway Tours offers several other tours, some centered around other parts of the city or with specific themes like architecture, crime and ghosts.

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Inside Chicago Walking Tours - Dazzling Interiors of the Loop

Inside Chicago Walking Tours' The World Within: Inside the Dazzling Interiors of the Loop tour reveals interior architectural details that visitors might otherwise have missed. 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 adults 11 and older and $25 for children ages 6 to 10 and patrons 65 and older. Children ages 5 and younger tour for free. Inside Chicago also offers other architecture-oriented tours as well as private tours.

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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

Bobby's Bike Hike Chicago's Bikes, Bites & Brews Tour – Signature Dishes, as its name indicates, combines bicycling, food and beer. The four-hour, 13-mile ride traverses the Streeterville, 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 $66.75. There are also discounts for students, military members and senior citizens. Bobby's Bike Hike Chicago offers additional bike, walking and food tours that take travelers to other parts of the city, including Chinatown.

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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.

City Segway Tours

City Segway Tours takes travelers to some of Chicago's best-known and most popular destinations, including Adler Planetarium, the Field Museum, Grant Park, Monroe Harbor, Millennium Park, the Shedd Aquarium and Soldier Field. Reviewers regularly praise the guides as informative, helpful and entertaining. Tickets for the approximately three-hour tours start at $70 and include the use of a two-wheeled Segway vehicle and a helmet. Riders must be at least 12 years old. Groups are limited to eight people. City Segway Tours also offers private tours of Chicago as well as tours less than three hours.

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 13 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 $46 for adults and $30 for children (with a 10% discount when purchased online). In addition to its classic ticket, Big Bus Chicago offers a premium ticket valid for two days and includes admission to the Chicago Architecture Center.

Tastebud Tours - Taste Chicago

Tastebud Tours' Taste 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

Chicago Prohibition Tours explore a notoriously eventful moment in the city's history. Tours visit 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. 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 $45, do not include food or drinks, which can be ordered separately at tour-takers' discretion.

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 $70 for a single kayak or $140 for a tandem (two-person) kayak for the 90-minute tour. Urban Kayak also offers cheaper one-hour outings as well as 90-minute excursions starting at Monroe Harbor.

Shoreline Sightseeing Classic Lake Tours

Shoreline Sightseeing Classic 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 - Lakeside Architecture Sail

Tall Ship Windy's Lakeside Architecture Sail features views of Chicago's skyline 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 $14 for children ages 12 and younger. 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

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.

Seadog Lakefront Speedboat Tour

Seadog Lakefront Speedboat Tours feature high-speed, musically enhanced 30-minute tours of the Lake Michigan shoreline and afford striking views of the Chicago skyline. Onboard guides offer historical and architectural information about some of the sights, which include Navy Pier (the departure point), Buckingham Fountain, Grant Park and the Museum Campus. Visitors praise the crew's knowledge and charisma. Tour-takers are allowed to bring their own adult beverages on board. Ticket prices start at $27.95 for adults and $20.95 for kids ages 12 and younger. Kids ages 2 and younger ride free, but do require a ticket. The boat is open-air, which means travelers might get wet. Seadog Cruises also offer a longer 75-minute ride and a faster "Extreme Thrill Ride."

John Rodwan, Contributor

John G. Rodwan Jr. has written about arts and entertainment, food and beverages, hospitality ...  Read more

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