Illinois
Sightseeing Walking Tours

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Our most recommended Illinois Sightseeing Walking Tours

Chicago River: 1.5-Hour Guided Architecture Cruise

1. Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago: 1.5-Hour Lake and River Architecture Cruise

2. Chicago: 1.5-Hour Lake and River Architecture Cruise

Experience an architecture cruise along the Chicago River and Lake Michigan, a family tradition since 1935. Admire Chicago’s historic and ever-changing skyline with a local expert guide as you cruise through the city. Choose between the open-air decks or the comfort of the climate-controlled interiors during the cruise. Start the cruise at Michigan Avenue (DuSable) bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. Learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building, the circular Marina City Towers, the AON Center, and modernist structures like Aqua, Trump Tower, Nuveen, and the Vista Tower. After passing through the Chicago Lock and cruising past Navy Pier, admire the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Here you can also see the twin super-skyscrapers, the famous Willis (formerly Sears) Tower, and the John Hancock Building. See the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. Enjoy several vantage points for memorable pictures throughout, and finally arrive back at Du Sable Bridge on Michigan Avenue.

Chicago: 45-Minute Family-Friendly Architecture River Cruise

3. Chicago: 45-Minute Family-Friendly Architecture River Cruise

Admire Chicago’s impressive architecture from a unique perspective aboard a cruise sailing down the Chicago River, which features an indoor and outdoor deck, along with live commentary tailored to entertain the whole family. Treat yourself to a full-service cash bar at your own expense. Experience the best of the Chicago River from Lakeshore Drive to the Willis Tower, navigating along the South branch of the river, before heading back past the Chicago Riverwalk towards Lake Shore Drive and Lake Michigan. Be entertained by the fun and experienced tour guides as they explain the history behind Chicago’s buildings along the river and the exceptional architects who created this ever-changing skyline. Enjoy the most relaxing way to sightsee in Chicago, exploring the city free of traffic, noise, and congestion. Make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Explore the open-air decks that allow you to feel the cooling river breeze and see the city from many vantage points that provide perfect photo opportunities.

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

4. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

Chicago: Big Bus Open-Top Panoramic Night Tour

5. Chicago: Big Bus Open-Top Panoramic Night Tour

From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 75-minute, panoramic tour and take in unique views of the Chicago skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper, and see architectural marvels like the John Hancock Center, the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. Finish your tour at the Chicago Riverwalk, with the knowledge that you can continue exploring the city with confidence. From the pioneering skyscrapers to the Great Chicago Fire, this night tour will take you on a journey you won't soon forget. Be sure to soak up the exciting atmosphere that makes the Windy City such a fascinating and dynamic place.

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

6. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago: Art Institute Skip-the-Line Tour with Guide

7. Chicago: Art Institute Skip-the-Line Tour with Guide

Experience a guided tour around some of the world’s greatest and most iconic art pieces at the Art Institute of Chicago. Avoid the crowds and lines and meet your expert guide at the Institute 30 minutes before opening time. Explore the expansive collection, learning more about both contemporary and classic pieces. Although the museum usually hosts 1.79 million people per year, you will be able to stroll among the pieces at leisure, getting up close and personal with works by famous and infamous artists like Edward Hopper, Pablo Picasso, Salvador Dali and Andy Warhol. The Art Institute of Chicago is home to the greatest collection of Impressionist artwork in the world. Your guide will provide expert information on the collection and the museum’s history and hidden gems.

Chicago Underground Donut Tour

8. Chicago Underground Donut Tour

Take a donut tour of the windy city, and discover the best Chicago has to offer. At each location, you will taste a curated sample of the best donuts. Some of the stops on this downtown tour include Stan's Donuts, Do-Rite Donuts, and Firecakes Donuts, true donut institutions. This two hour walking tour is led by a passionate donut expert who will guide you to some of Chicago's best donut locales. This tour caters to all size groups, both large and small. The donut tour is great for bachelor and bachelorette parties, birthdays, family reunions, weekend getaways, or even corporate events. There are two versions of the Donut Tour: The Classic Downtown Tour, as well as a local neighborhood tour in Wicker Park. Both are great options if you're excited about donuts. It really just depends on what neighborhood you want to explore: if you want to stay downtown or if you want to venture out to the Wicker Park & Bucktown neighborhoods to see how "the locals do it". In either case, don't hesitate to join the tour. Buy your tickets today!

Chicago: Treasures of the Golden Age Walking Tour

9. Chicago: Treasures of the Golden Age Walking Tour

This Historic Treasures of Chicago tour covers the most significant historic architectural landmarks in Chicago’s Loop. Your expert guide, trained by the Chicago Architecture Center, will focus on great cultural buildings from the late 19th and early 20th centuries, which harkened back to earlier time periods and were designed in revival styles such as Beaux Arts, neo-Georgian and neo-Gothic. Marvel at exteriors and interiors of dazzling beauty and startling originality, and get a glimpse inside some of the city's most beloved buildings.    The highlights of this walking tour will include the Chicago Cultural Center, home to the world's largest Tiffany dome; the iconic Marshall Field's department store, now Macy's on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

Chicago: 2.5-Hour Taste of Chinatown Food Walking Tour

10. Chicago: 2.5-Hour Taste of Chinatown Food Walking Tour

Explore the complex layers of Chinese culture and the many contributions these people have made to both Chicago and the world. And what better way to show off Chinese culture then through food? Your guide will take the confusion and language barrier away as you sample your way through a variety of Chinatown's best restaurants and well-kept secret recipes. Start your tour at Phoenix Restaurant and begin with some yummy dim sum dumplings and a traditional Chinese tea tasting. Next, it will be time for a sweet treat - buttery custard tarts from Chinatown's oldest bakery. Then, try a unique and delicious spicy meat sandwich from the Xi'an region. Afterward, stroll through the charming Chinatown Square with its ethnic grocery stores and souvenir shops. Finally, taste a sampling of succulent dry chili chicken, followed by the famous spicy Szechuan hot pot. You'll have traveled all over China but only walked a few blocks on this delicious tour of one of Chicago's most fascinating neighborhoods.

Frequently asked questions about Illinois Sightseeing Walking Tours

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Other Sightseeing Options in Illinois

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What people are saying about Illinois

Overall rating

4.7 / 5

based on 624 reviews

We had an extremely knowledgeable and personable guide on our cruise, the boat was clean and comfortable, overall a great way to learn about Chicago architecture and history at the same time.

Tour guide narrator was excellent. Extremely knowledgeable and entertaining. Duration of 45 minutes was perfect.

Great way to learn the history and some information about the amazing architecture of this beautiful city!

Very informative and relaxing to sit and see all of these incredible buildings.

Great tour about the history of gangsters and ghosts in Chicago!