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Chicago Tours and Activities

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Here are your 166 search results for Tours, Attractions & Activities in Chicago, United States

Chicago Food Tour: Chicago-Style Pizza, Beer, Brownies, and Hot Dogs

Chicago Food Tour: Chicago-Style Pizza, Beer, Brownies, and Hot Dogs - Chicago, Illinois
Star Rating

Duration: 3 hours
Location: Chicago, Illinois

Special Offer
From USD
$53.10

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 ... More info ›

Special Offer - Book and save 6% compared to the local supplier's prices! - Book Now!

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.

Follow your knowledgeable guide through downtown Chicago and visit a number of stunning indoor spaces including the historic Palmer House Hotel, the Walnut Room and Macy’s. Your guide also takes you to various spots for samples of some of Chicago’s favorite foods such as pizza, hot dogs, brownies, and beer from a local brewery.

Architectural highlights include Millennium Park, a modern town square with a collection of art, architecture, and gardens that provide a stunning backdrop for hundreds of cultural events. Nearby, walk along the Chicago River, a system of waterways that links to the Great Lakes, the Mississippi River and the Gulf of Mexico. It's a key reason that Chicago became a powerhouse city,
facilitating trade in the Midwest and beyond. If you visit in March, don't be alarmed if the water appears radioactive green — it's actually a St Patrick's Day tradition to add (non-toxic) dye to the river for the festivities.

Step inside the gorgeous and historic Palmer Hotel, host to many luminaries since it opened in 1875. Presidential candidates Grover Cleveland and Ulysses S. Grant stayed in the luxurious hotel, as did writers Mark Twain, Oscar Wilde and L. Frank Baum. Your guide shows you ornate interiors and shares the colorful history of this hotel. Then see the iconic Marshall Field’s Building, with its beautiful atrium, mosaic ceiling designed by Tiffany & Co, and famous outdoor clocks.

During colder months, your guide leads you on a route through the Chicago Pedway system, a network of tunnels, ground-level concourses and bridges that connects sites throughout Chicago’s central business district, keeping you comfortably warm. During warmer times of the year, walk along the large scenic promenades of the Loop.

Expect to walk at a leisurely pace for 1.5 miles during the 3-hour tour, suitable for most fitness levels, with plenty of stops for tastings and photo ops. All tastings and beverages are included.

Special Offer - Book and save 6% compared to the local supplier's prices! - Book Now!

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Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs

Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs - Chicago, Illinois
Star Rating

Duration: 4 hours
Location: Chicago, Illinois

Special Offer
From USD
$71.55

Taste the flavors of Chicago, both edible and cultural, on a bike tour through the city. Sample four of Chicago’s favorite foods and drinks –pizza, cupcakes, hot dogs and beer – and experience the city as you make your way through the neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park with a local guide.

Combine a bike tour of beautiful downtown Chicago with a food tour of Chicago’s four most coveted culinary delights – pizza, beer, cupcakes and hot dogs! You will undoubtedly work up an appetite on this four-hour tour of Chicago’s most iconic neighborhoods ... More info ›

Special Offer - Book and save 6% compared to the local supplier's prices! - Book Now!

Taste the flavors of Chicago, both edible and cultural, on a bike tour through the city. Sample four of Chicago’s favorite foods and drinks –pizza, cupcakes, hot dogs and beer – and experience the city as you make your way through the neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park with a local guide.

Combine a bike tour of beautiful downtown Chicago with a food tour of Chicago’s four most coveted culinary delights – pizza, beer, cupcakes and hot dogs! You will undoubtedly work up an appetite on this four-hour tour of Chicago’s most iconic neighborhoods. Along the way, stop at two breweries, a pizza shop, a hot dog stand and a cupcake bakery.

Where did deep-dish pizza come from? What makes a craft beer taste so good? What is the difference between a Chicago-style hot dog and a regular hot dog? Find the answers to these questions and more as you wind through the streets of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park with your guide. You’ll learn the history of the neighborhoods and the traditions of the food, making it taste even better.

Special Offer - Book and save 6% compared to the local supplier's prices! - Book Now!

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Old Chicago Gangster Bicycle Tour

Old Chicago Gangster Bicycle Tour - Chicago, Illinois
Star Rating

Duration: 4 hours
Location: Chicago, Illinois

Special Offer
From USD
$57.46

Travel back in time to the seamier side of Chicago on this guided bicycle tour that takes you to the Southside hangouts of notorious Chicago gangsters like Al Capone. Learn the history of the Chicago Outfit as you cycle through Bridgeport, Chinatown, Palmisano Park and more ... More info ›

Special Offer - Book and save 6% compared to the local supplier's prices! - Book Now!

Travel back in time to the seamier side of Chicago on this guided bicycle tour that takes you to the Southside hangouts of notorious Chicago gangsters like Al Capone. Learn the history of the Chicago Outfit as you cycle through Bridgeport, Chinatown, Palmisano Park and more. Bike along scenic paths on Chicago’s Lakeshore en route to see famous mob homes and haunts, Chicago’s former red-light district, and Al Capone’s stomping grounds. You'll get a glimpse into the Windy City's underworld while enjoying a fun and informative bike ride!

Meet your guide and get outfitted with safety gear and a bicycle. From there, pedal off to learn about Chicago’s mobster history. Your expert guide leads you past the territories of Al Capone and other famous gangsters who ruled territories of Chicago’s South Side during the Prohibition era.

Along the 13-mile (21-km) route, cycle past former mob homes and hangouts that were popular with gangsters in the early 20th century. Many of the homes you see belonged to members of the Chicago Outfit, a crime syndicate that was once the biggest criminal organization in the Midwestern United States.

Your tour takes you other sites related to the mob, such as Chinatown, Bridgeport, the old Levee District, which was once a red-light district. Stop at Palmisano Park, an innovative park that was built on the site of an old rock quarry and former dump. Even this lovely green space has a scandalous story that was exposed by reporters from the Chicago Sun Times in 2004.

Your tour isn't all about crime. It also take you to scenic sites such as the Prairie Avenue District, which became a fashionable residential district after the 1871 Great Chicago Fire and is on the National Register of Historic Places. Bike along lakeshore paths that afford great views of Lake Michigan, and glide past McCormick Place and Museum Campus. You'll even enjoy classic Italian beef sandwiches at a Chicago original hangout. 

Expect to ride about 13 miles on a route considered moderate to advanced, with plenty of stops to rest and listen to your guide’s informative commentary. Your tour ends after about three hours when you return to your starting point.

Special Offer - Book and save 6% compared to the local supplier's prices! - Book Now!

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Chicago Bike Rental

Chicago Bike Rental - Chicago, Illinois
Star Rating

Duration: Flexible
Location: Chicago, Illinois

Special Offer
From USD
$18.49

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium ... More info ›

Special Offer - Book and save 27% compared to the local supplier's prices! - Book Now!

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium. This is a fun and active way to experience the city with the whole family, and you can enjoy the flexibility to create your own itinerary with the help of your provided map.

You’ll receive a helmet, bike lock and detailed map to help you easily navigate the city.

This full-day bike rental allows you to explore Chicago at your own pace. Choose from a variety of attractions and create your own sightseeing itinerary to fit your whole family's interests and preferences.

Start cycling along the shores of Lake Michigan for gorgeous views of Navy Pier, featuring family-friendly attractions, entertainment, shopping and dining.

Continue to Millennium Park, a lively gathering spot that's home to Cloud Gate (The Bean). Stop here to take a photo of yourself reflected in the mirror of this famous bean-shaped sculpture!

Head north to Lincoln Park, a large lakeside community and park home to the Lincoln Park Zoo. Entrance is free, so you can hop off your bike to explore some amazing animal exhibits.

Further south, you’ll find Grant Park, whose Buckingham Fountain stands tall as one of the largest fountains in the world!

For a taste of Chicago’s passion for art and science, head to Museum Campus, a 57-acre (23-hectare) park on Lake Michigan that’s home to the Adler Planetarium, the Shedd Aquarium and the Field Museum of Natural History, as well as the Soldier Field football stadium.

Of course, you can’t miss Wrigley Field, where the Chicago Cubs play! After your independent bike tour, drop your bike off at the rental shop by 5pm.

Special Offer - Book and save 27% compared to the local supplier's prices! - Book Now!

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Booking.com

Duneland Wine Country with Gourmet Lunch

Duneland Wine Country with Gourmet Lunch - Chicago, Illinois
Star Rating

Duration: 7 hours
Location: Chicago, Illinois

From USD
$175.00

Just over the Illinois border along the southern tip of Lake Michigan lie the Indiana Dunes. In the charming villages that dot the area known as Duneland, you’ll find artisan wineries featuring wines made from grapes grown in Indiana and other Midwest states ... More info ›

Just over the Illinois border along the southern tip of Lake Michigan lie the Indiana Dunes. In the charming villages that dot the area known as Duneland, you’ll find artisan wineries featuring wines made from grapes grown in Indiana and other Midwest states. Let an experienced winemaker accompany you from downtown Chicago to three tasting rooms and provide insight about this unique terroir. Your full-day itinerary includes a luxurious lunch of contemporary, farm-fresh fare in Chesterton.

Meet at the InterContinental Chicago Magnificent Mile or receive pickup from your accommodation in the Chicago Loop. You’ll depart for Duneland wine country towns located around the Indiana Dunes, just a stone's throw from downtown Chicago and roughly one hour from the Loop.

This full-day of wine tasting includes stops at three wineries where you’ll learn from local winemakers about the hybrid grapes grown in the Midwest (tasting fees included). These wines have different aromas and flavor profiles from wines made in Europe and California, so both novices and aficionados will increase their knowledge of all things wine. Your guide is a licensed wine distributor who shares intimate knowledge of the area’s wine industry.

A leisurely gourmet lunch with local farm ingredients is served in Chesterton, located in the heart of the Indiana Dunes National Lakeshore, before hotel drop-off in the late afternoon.

Less info

Chicago Architectural River Cruise

Chicago Architectural River Cruise - Chicago, Illinois
Star Rating

Duration: 90 minutes
Location: Chicago, Illinois

From USD
$48.16

Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city that defied all expectations … even the laws of gravity.

This 90 minute Architectural cruise sails on the Chicago River. It is fully narrated, discussing the buildings of Chicago, as well as some historical anecdotes!

On this tour you will travel to the North, South and the Main branches of the Chicago River to see the world renowned architecture of Chicago ... More info ›

Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city that defied all expectations … even the laws of gravity.

This 90 minute Architectural cruise sails on the Chicago River. It is fully narrated, discussing the buildings of Chicago, as well as some historical anecdotes!

On this tour you will travel to the North, South and the Main branches of the Chicago River to see the world renowned architecture of Chicago. Take in the views as you pass by more than 50 skyscrapers, bascule bridges and historic sites. You will pass by Lake Point Tower, Trump Tower, NBC Tower, Wrigley Building, Tribune Tower, Marina City, Aqua Tower, Navy Pier, Willis Tower (Sears Tower), The John Hancock Building and many more architectural sites.

Come grab a seat and enjoy complimentary Starbucks Coffee, Twining Tea, Coca-Cola soft drinks, lemonade and cookies. Beer and wine is also available for purchase.

Less info