Top 10 Guided Local Tours in Chicago

Amazing Local Flavors of Chicago Food Tour
Amazing Local Flavors of Chicago Food Tour
         
Chicago, IL
3 hours
from 50 USD
Confused on what to see and do while in Chicago? It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond. Combine them all by tantalizing all of your senses with a 3 hour small- group walking food excursion lead by a professional guide. You'll indulge in 5-6 of Chicago's quintessential staples while feeding your mind with intriguing and memorable tidbits along the way. Before you know it, you'll feel like a local.
Chicago City Sights Helicopter Tour
Chicago City Sights Helicopter Tour
         
Chicago, IL
30 minutes
from 149 USD
Experience all of Chicago's best sights from the air on this exciting helicopter tour! Aboard a state-of-the-art helicopter, you'll enjoy a magnificent view of Lake Michigan and fly past several top Chicago attractions like Willis Tower, Wrigley Field, Navy Pier, Millennium Park, the Shedd Aquarium and Lincoln Park. Your pilot will provide expert commentary about the sights you see and can answer any questions you have.
Chicago Sightseeing Tour with Optional Boat Cruise
Chicago Sightseeing Tour with Optional Boat Cruise
         
Chicago, IL
Varies
from 37 USD
Don't miss Chicago's famous sights and fabulous views on this small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like the Willis (Sears) Tower, Wrigley Field, downtown Chicago (known as 'the Loop') and more! Along the way, your guide will provide historical and informational commentary about the area and its beautiful attractions. You also have the option to upgrade to include a 60-minute boat tour down the Chicago River! This open-top boat offers the perfect vantage point to admire the city's renowned architecture.
Chicago Prohibition Tour
Chicago Prohibition Tour
         
Chicago, IL
3.5 hours
from 45 USD
Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the sale of alcohol was banned for more than a decade in the United States, and the subsequent popularity of illicit establishments where liquor, jazz, and mobsters ruled. An air-conditioned coach shuffles you from bar to bar, so feel free to buy a drink or two. This small-group tour, limited to 20 people, ensures a more customized experience with your guide.
Tastes of Chicago Walking Tour: Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs
Tastes of Chicago Walking Tour: Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs
         
Chicago, IL
3 hours
from 55 USD
Experience Chicago on a walking and food tour of the central business district. Visits to legendary sites such as Palmer House Hotel, Marshall Field's Building, and Millennium Park are punctuated by stops in local food joints for samples of Chicago's favorite bites. Your expert guide shares the history of Chicago's most iconic buildings and foods as you walk around the Windy City's legendary downtown Loop.
Chicago Lakefront Neighborhoods Bicycle Tour
Chicago Lakefront Neighborhoods Bicycle Tour
         
Chicago, IL
3 hours
from 48 USD
Accept no imitations! This tour taking you off the tourist beat and onto the quiet neighborhood streets, city parks, and packed beaches of the North Side of Chicago, giving you a glimpse as to how Chicagoans enjoy their beautiful city.
Chicago Segway Tour
Chicago Segway Tour
         
Chicago, IL
2 or 3 hours
from 65 USD
Hop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very own Segway, you'll see all the famous sights - Buckingham Fountain, Navy Pier, Lake Michigan and more.
Chicago Architecture River Cruise
Chicago Architecture River Cruise
         
Chicago, IL
60 minutes
from 34 USD
Experience one of the world's most beautiful cities on a 1-hour cruise on the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.
Chicago Walking Tour: Historic Loop Skyscrapers
Chicago Walking Tour: Historic Loop Skyscrapers
         
Chicago, IL
2 hours
from 18 USD
Perhaps Chicago's most identifiable claim to fame resides in its architecture. The prototype of the modern industrial metropolis arose from the charred landscape left by the Great Fire of 1871. Many of Chicago's surviving buildings are the forefathers of the great modern skyscrapers and on this walking tour you will discover the historic beginnings of the Chicago School of Architecture and the earliest skyscrapers, built between the 1870s and the 1930s.>
Chicago City Hop on Hop off Tour
Chicago City Hop on Hop off Tour
         
Chicago, IL
Flexible
from 33 USD
See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most popular attractions, then pick up the tour where you left off or get on at any other regular stop on the route. For individuals and families, this is the best way to see the sites in a day!