The 10 Best Sightseeing Tours in Chicago, Illinois (IL)

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour private guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol

Inclusions: Skip-the-Line Private Museum Tour , Professional Tour Guide Exclusively For You , Duration 2 - 2.5 Hours , Wheelchair Friendly, All Entrance Fees

Exclusions: Tour price does NOT include hotel pickup or drop-off (we recommend UBER or Taxi), Tour price does NOT include gratuities (optional)

2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic downtown Chicago and explore the beautiful Grant Park, around the Buckingham Fountain, near the Museum Campus and near the lakefront. Or take our Riverwalk tour to explore the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue and passing by Millennium Park. No matter which tour you choose, it will be a memory lasting a lifetime!

Inclusions: 2 hour guided Segway Tour of Chicago, IL

Exclusions: Gratuity for Tour Guide, Does not include meals

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more! Marvel at the stunning Chicago skyline and discover why Chicago’s architecture is among the best in the world Get around The Loop like a local: at street level, underground, elevated rails or perhaps even on the water Enjoy a couple of classic made-in-Chicago snacks like Chicago-style popcorn and homemade chocolate Get a taste for Chicago’s most famous food in one of the city’s most historic neighborhoods Discover why locals have so much passion for their Chicago-style classics

Inclusions: Professional Local Guide, Popcorn Tasting, Chocolate Tasting, Water Taxi or Subway Ticket, Chicago-style hot dog, Deep dish pizza, Italian Beef

Exclusions: Gratuity

Taste all of Chicago’s classic eats on this four-hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure. The journey is 14 miles (traversed at a leisurely pace) and includes deep dish pizza, a gourmet brownie, a Chicago-style hot dog, and a few samples of local craft beer! On the daytime version of the tour, you’ll drink in the sights of Chicago’s beautiful north side neighborhoods, including historic Wrigleyville, home to our intrepid Chicago Cubs baseball team. On the nighttime version, you'll ride through the party districts of downtown and see the lights of Buckingham Fountain and the glorious skyline. Then you’ll get a chance to cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this rip-roaring good time! You’ll leave with a profound understanding of our town, even if you only came for the beer.

Inclusions: Bicycle, Helmet, Water Bottle, Expert local guide, Food and beer samples

Exclusions: Gratuity for guide (15-20% suggested, PayPal & Venmo available)

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

Inclusions: Live commentary on board, Local guide (docents), River sightseeing cruise

Exclusions: Drinks & light snacks (available to purchase)

Welcome to Chicago River Boat Architecture Tours! We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it’s hard to cover all of the design and building treasures that make up the Windy City today. If you’re ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago. Tour departures from 465 N. McClurg Ct.

Inclusions: Local guide, Port pickup and drop-off, Bottled water, Coffee and/or Tea

Exclusions: Alcoholic drinks (available to purchase)

We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't see anything that truly celebrated donuts in all their glory, hence the Underground Donut Tour was born. This tour is for anyone who truly enjoys donuts. At each location, you'll be able to try a curated sample of one of that location's best donuts. Many locations offer vegan, gluten or nut free options, however, please make sure to let us know ahead of the tour, so we can make sure to highlight those specifically for you. Our tours include such favorites as Do-Rite Donuts, Firecakes, Stans, and Doughnut Vault. Please send us an email if you are looking for a specific location, as tours vary by day.

Inclusions: Food tasting

Exclusions: Gratuities

Experience one of the world’s most beautiful cities on a cruise down 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 (Sears 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.

Inclusions: Guided architecture cruise of the historic Chicago River, Live commentary on board

Exclusions: Drinks (available for purchase)

Stroll through the beautiful streets of downtown Chicago and taste all of the Windy City’s favorite eats! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, whose walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Traveler Magazine. This is Bobby’s quintessential culinary walking tour, complete with a slice of deep dish pizza, a Chicago-style hotdog, Italian beef sandwich, chocolates and pastries, as well as locally crafted beer. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks, including Millennium Park, State Street and Chicago Theatre, Chicago Riverwalk, Michigan Avenue, and the Wrigley Building, all the while regaling you with tales from Chicago’s rich food-centric history. This tour is sure to make memories that will last a lifetime!

Inclusions: Food tasting, Expert tour guide

Exclusions: Hotel pickup and drop-off, Gratuity for guide (15-20% suggested, Venmo and PayPal available), Local craft beer samples can be added for a fee (Three 9oz pours)

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago! You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive.

Inclusions: Walking tour of Chicago’s gangsters and ghost stories

Exclusions: Gratuities