These guided tours of the Windy City will appeal to foodies, architecture fans, and history lovers alike.
With the assistance of a local, one of the finest ways to explore a new city is to take in the sights. In light of this, U.S. News selected 14 of Chicago’s top guided tours. With these tours, you may learn about the cultural and historical background of the Windy City while taking a river ride past the Willis Tower or enjoying some of Chicago’s greatest deep-dish pizza.
Gateway to the West Loop Food Tour with Chicago Food Planet
The West Loop Gateway to Chicago Food Planet has some of the city’s best foods, including pizza, donuts, and burgers. The three-hour trip focuses on the fantastic food scene in the West Loop neighborhood and offers insider knowledge of the history and culture of the region. Travelers frequently laud guides for their expertise and passion. Adult ticket rates begin at $65 and those for kids 12 and under begin at $50. The tour is deemed worthwhile by reviewers due to the copious amounts of food offered. Furthermore, trips don’t need a lot of walking and group numbers are limited to 14 persons. Thursday through Sunday at 1 p.m. there are tours available. Chicago Food Planet also provides excursions through the city’s Chinatown.
Chicago Lakefront/Museum Campus Segway Tours offered by Absolutely Chicago
A number of the city’s most well-known attractions are featured on the Chicago Lakefront/Museum Campus tour provided by Absolutely Chicago Segway Tours, including Millennium Park (the tour’s starting point), Grant Park, Monroe Harbor, the Field Museum, Shedd Aquarium, Soldier Field, and the Adler Planetarium. Easy-to-ride, two-wheeled, battery-powered cars take around 2 1/2 hours to travel the 8 miles. Participants laud the expertise and understanding of the tour leaders. Ticket prices range from $65 to $75 depending on the day and hour. The minimum age requirement for riders is twelve. Daily tours are offered. The company provides a number of additional excursions, some of which are focused on different areas of the city or have particular themes, such architecture, crime, or ghosts.
Inside Chicago Walking Tours: The Loop’s Glamorous Interiors
The World Within: Dazzling Interiors of the Loop tour by Inside Chicago Walking Tours highlights internal architectural aspects that guests might otherwise overlook. A gilded 80-foot-high ceiling, art deco lobbies, early Frank Lloyd Wright designs, and rooms with stained-glass mosaics are among of the highlights of the two-hour tour. The 1 1/2 miles of walking required for this tour, according to reviews, is an engaging way to learn about Chicago’s history and its many distinctive structures. Participants 11 and older can purchase tickets for $30, while those aged 5 to 10 and 65 and over can only pay $25. Tours are free for visitors under the age of four. Saturday at 11 a.m. is when outings start. Along with private tours, Inside Chicago also provides other architecture-focused tours.
Bikes, Bites, and Brews Tour with Signature Dishes at Bobby’s Bike Hike Chicago
This tour incorporates biking, eating, and drinking. With stops for pizza, beer, cupcakes, and hot dogs, the four-hour, 13-mile ride travels through the Gold Coast, Lakeview, Wrigleyville, and Lincoln Park districts. Reviewers laud the guides and say that the trip is a fantastic way to learn about the city. For weekday rides, adult tickets that include the bike rental, meals, and beverages start at $76.99. (weekend rides are slightly more expensive). Participants must be older than 21. Try Bobby’s Bike Hike Chicago’s Family Food & Bike Tour if you’re traveling with children.
Original Chicago Pizza Tour: Chicago Pizza Tours
The Original Chicago Pizza Tour lets you take part in one of Chicago’s most distinctive culinary phenomena. You’ll visit four locally owned neighborhood pizzerias and try six or more slices during this three and a half-hour tour. The tour leaders’ knowledge and entertainment are highly praised by reviewers. Others assert that the tour covers Chicago history, architecture, and culture in addition to pizza. Adult and child tickets start at $60 and $36, respectively. Take one of the company’s other food tours to learn more about the city’s pizza from different perspectives. Some of these trips mix pizza and cocktails or are centered on the largest slices.
Chicago Hop-On Hop-Off Tour with Big Bus
Customers on Big Bus Chicago’s Hop-On Hop-Off Tours can customize their outings by spending as much time as they like at any of the 12 stops throughout the eight hours included in the regular package. Visitors to tours can “jump off” a bus and spend some time at well-known locations like Skydeck Chicago, Navy Pier, Soldier Field, or Millennium Park before “hopping on” a different vehicle at a later time. Every 30 to 45 minutes, buses run, and they come with commentary-giving guides. Guides are regularly praised by tourists for being both entertaining and educational. The signage is one complaint from passengers; some have trouble finding the bus stops at specific sites. Adult and child tickets start at $49 and $30, respectively (though you may be able to score a discount by purchasing online in advance). Big Bus Chicago also provides a premium ticket that is good for two days in addition to its standard ticket.
Chicago-themed tours offered by Tastebud
The Taste of Chicago tour by Tastebud Tours highlights the city’s Loop neighborhood. The three-hour tour stops at a number of eateries and stores where you can buy the famous Chicago deep-dish pizza, popcorn, sandwiches, and treats. The tour also includes non-gastronomic landmarks that are popular with tourists, such as the Marshall Field and Company Building, the Art Institute of Chicago, and the Chicago Cultural Center. Guides are frequently praised for their historical expertise and passion for Chicago. All meal is included in the tickets, which start at $59.50. (Where available, adult beverages may be purchased separately.) There can only be 18 persons in a group. Along with individual tours, Tastebud Tours also provides additional food-related activities.
River Cruise for the Chicago Architecture Foundation
During the Chicago Architecture Foundation’s River Cruise, docents from the Chicago Architecture Center regale passengers with the histories of more than 50 eminent structures as they are transported along the Chicago River. Reviewers frequently give the volunteer docents high marks for their extensive knowledge of the city’s history and architectural features. The cruise ships, which are a part of Chicago’s First Lady Cruises’ fleet, can accommodate up to 250 passengers and have open-air top decks and full-service bars. For daytime cruises, tickets for the 90-minute excursions cost about $45. Evening excursions cost a little more money. You can also visit the Chicago Architecture Center, which normally costs $12 on its own, for an extra $5.
Original Chicago Prohibition Tour
Chicago Prohibition Tours delve into this infamously dramatic period in the city’s past. In its centerpiece, over the duration of three and a half hours, a bus travels to the locations of four defunct speakeasies. In addition to sharing historical details, guides describe the kind of beverages that would be typical of those consumed illegally during the Prohibition era. The business will also provide transportation for you between locations. Reviewers gush about the quick-witted guide and claim that both locals and tourists will appreciate this encounter. Others love how distinctive each bar is on the tour. Tickets, which start at $55, do not include food or beverages; however, tour participants are free to order these items separately. This tour is also available in a 2-and-a-half-hour walking version.
Historic Chicago Tour with Urban Kayak on the Chicago Riverwalk
Take the Historic Chicago Tour with Urban Kayak to get a “duck’s eye” view of the city. Starting at the Riverwalk, tour participants paddle their kayaks along the Chicago River’s major branch, making stops at several historical sites along the way to learn more about the city’s renowned architecture. Even for beginners, this is a terrific experience, according to reviews. Others remark that the knowledgeable guides are adept at controlling the boat traffic. Tickets for the roughly two-hour tour cost about $65 for a single kayak or $130 for a tandem (two-person) kayak. Additionally, Urban Kayak provides classes for paddleboarding and kayak rentals.
Skyline Lake Tours – Shoreline Sightseeing
Cruises around the shoreline of Lake Michigan provide passengers with unmatched views of Chicago’s cityscape as well as several photo possibilities. Views of famous sites like the John Hancock Center, the Willis Tower (also known as the Sears Tower), the Adler Planetarium, and the Field Museum are available during the 6-mile tour. Reviewers claim that these famous buildings are far more noticeable from the sea than they are from the ground. Many people cite this tour as the high point of their trip to Chicago. The 40-minute narrated boat tours begin at $23 for adults and $8 for kids aged 3 to 12. Young children under 2 ride free. Drinks are available for purchase at the onboard cash bar. Along the Chicago River, Shoreline Sightseeing also provides excursions that concentrate on architecture.
Chicago Skyline Sail on the Tall Ship Windy
The 148-foot, four-masted schooner Tall Ship Windy offers views of the city from its deck during its Chicago Skyline Sail. Reviewers laud the breathtaking vistas of the city’s magnificent structures and, weather permitting, the unique sensation of being able to sail rather than rely on the boat’s power. Participants in the tour also praise the crew members for their professionalism. Tickets for the trips in the summer and fall start at $37 for adults and $17 for kids under the age of 12; infants under the age of one year ride for free. There is a complete bar on board Tall Ship Windy (drinks are not included in the ticket price.) Tall Ship Windy offers 75-minute excursions every day in addition to fireworks cruises and pirate-themed excursions on particular dates.
Tours of Crime in Chicago
In a number of Chicago areas, including the Gold Coast, Lincoln Park, the Loop, the Magnificent Mile, Old Town, and River North, Chicago Crime Tours visit well-known crime locations. The bus trip, which lasts for about two hours, stops at the locations of the St. Valentine’s Day Massacre as well as the places where gangsters like Hymie Weiss were murdered. It also stops at locations where people like Leopold and Loeb, Frank “the Enforcer” Nitti, and Al Capone formerly lived. The excursions are praised by reviewers for offering a distinctive perspective on Chicago’s colorful history. Tickets can be bought in advance (recommended) or on the bus for about $40. Additional tours include a pizza and crime strolling tour and a nighttime crime tour.
Hornblower City Cruises: Seadog Lakefront Speedboat Tour
During this rapid, musically enhanced 30-minute journey, zip across Lake Michigan. You’ll get some great views of the Chicago skyline and hear some descriptions of the locations while riding. Visitors laud the crew’s enthusiasm and expertise. They take pleasure in riding the waves as well. Adult tickets cost roughly $30, while children aged three to twelve pay $20. Children under 2 ride free, although they still need a ticket. Since the boat is open to the elements, passengers may become wet. City Cruises offers a wide range of additional boating excursions, including an intense thrill trip.