Top 25 Chicago Tours, Events & Activities

It’s really hard to visit Chicago and know the best Chicago tours, activities, and events to check out during your stay. It’s a huge city!  You don’t want to miss anything, and you want to explore with the top, most trusted Chicago tour operators.

Well, it turns out the city isn’t quite as big as it looks or feels. We’re here to help you feel like a native and spend your time (and money!) wisely when considering Chicago’s tour and experience options.

Inside this guide, we’re going to highlight 25+ Chicago tours and activities that locals and visitors alike absolutely should not miss.

Lace Up for a Chicago (Food) Walking Tour

Love to explore new cities on foot?

You’re in luck:

There are plenty of Chicago sightseeing tours designed for folks who love to walk. Chicago walking tours are affordable and often move at a pace that let you linger to take photos — and maybe note a few spots to check out on your own later!

#1 Chow Down With Chicago Food Planet Tours

chicago tours best walking

Photo Source: Chicago Food Planet

There aren’t enough days in the year to try all of the incredible food destinations and restaurants that Chicago has to offer. So why not hit the street and try several in a single day, all in 3 hours or less?

Chicago food tours are an incredible way to get to know a city, and it’s easy to see why. In just a few hours, food tours show you a variety of historical and cultural landmarks and take you behind the scenes to Chicago’s best restaurants, specialty food stores, and iconic mom-and-pop culinary hot spots — with plenty of bites and sips along the way to keep your belly full.

Food tours are definitely the tastiest way to hit the town — for tourists and locals alike!

Chicago Food Planet’s uber-popular Best in Chow Food Tour, which offers a whirlwind tour of the River North and Streeterville neighborhoods, plus a cornucopia of Chicago flavors: Italian beef at Al’s, deep-dish pizza at Lou Malnati’s, popcorn at Garrett’s, and more!

Or,  check out Gateway to the West Loop Food Tour, a delicious stroll down Randolph Street (which Food & Wine magazine named the city’s “Best Foodie Street”) featuring stops at local institutions such as Do-Rite Donuts, Bonci Pizza, Kuma’s Corner, Nonna’s, and Cemitas Puebla.

With 3,600+ TripAdvisor reviews since 2006, it’s easy to see why adding one of these Food Tours to your list is a no-brainer.

#2 Get With Chicago Greeter for a Free Chicago Walking Tour

chicago tours greeter walking

Photo Source: Chicago Greeter

Visiting Chicago from out of town?

Explore the city on foot with a free Chicago walking tour from a local guide through Chicago Greeters. Volunteer guides offer 2- to 4-hour walking tours customized to your interests, including different neighborhoods and cultural landmarks to explore. Just register for the tour at least 10 days in advance.

#3 Lace Up for a Walking Tour of Andersonville

Want to tour Chicago like a local? Head north to Andersonville, home of Certified Tour Guide Kevin Doerksen, and take a Chicago walking tour of this historically Swedish neighborhood.

Learn about the area’s Swedish roots and what makes it special today on this Andersonville walking tour with Wild Onion Tours.

Play Tourist on a Chicago Boat Tour

Rather see Chicago from the water?

You’re not alone.

Both the Chicago River and Lake Michigan offer cool breezes and a fantastic perspective on the city — the waterways, as well as the riverwalk and beaches up and down the Lake Michigan shore, are packed with sun seekers during the warm-weather months!

Chicago boat tours are an easy, breezy way to see the Second City from a new point of view.

BONUS: You can avoid the crush of tourists on the sidewalk and skip rush-hour traffic, too!

#4 Locals’ Trick: Hail a Chicago Water Taxi

chicago boat tours water taxi

Photo Source: Valpak

For a self-guided boat tour, hop aboard the Chicago Water Taxi during the warm months to get an affordable view of everything the city has to offer.

Check this:

The water taxi is more transit-oriented — focused on getting you from place to place rather than a traditional boat tour — but with stops everywhere from Chinatown to the West Loop and Michigan Avenue, there’s plenty for you to see!

INSIDER SCOOP: If you make it to Chinatown, you’ll be blown away by Ping Tom Memorial Park, the location of the Chinatown water taxi stop. If you’ve got a couple of hours to spare, consider taking a culinary journey on Chicago Food Planet’s immersive Chinatown food-tasting and cultural walking tour. You’ll eat at five authentic sit-down restaurants and learn some incredible cultural facts of this vibrant neighborhood along the way!

#5 Set Out On A Chicago Architecture River Tour

chicago river boat cruise tour

Photo Source: Chicago Architecture Foundation

At least two companies offer Chicago architecture boat tours starting in the spring months, both leaving from docks just off the Magnificent Mile on Michigan Avenue. Chicago Architecture Foundation’s boat tours aboard Chicago’s First Lady are led by trained docents, and Wendella offers boat tours of Chicago’s architectural wonders, too.

Why do we love these tours so much?

You’re going to come home with a phone full of Chicago building photos, sure. But unless you snag a spot on one of these boating tours (or really, really love to Google things) they’re not going to mean much a few days later. Wouldn’t it be cool to know exactly why that Mies van der Rohe building stopped you in your tracks during your visit?

#6 Sail From Navy Pier On a Lake Michigan Boat Cruise

chicago sailing boat tours

Photo Source: Instagram

You may be wondering:

What can we do if we’re spending the day at Navy Pier?

The waters of Lake Michigan as well as the Chicago River await you! Go old school (we’re talking pirate old school) aboard the Tall Ship Windy, which offers cruises throughout the day, including evening sails to see Navy Pier’s incredible fireworks shows. Or try something a bit more adventurous with one of Seadog’s 30-minute Extreme Thrill Rides, which top out at 45 miles per hour and guarantee you’ll have fun and get a little wet!

PRO TIP: Don’t leave Navy Pier hungry! Eat up on the best bite, sights and brews within the Navy Pier neighborhood on Chicago Food Planet’s Navy Pier Food & Culture Tour. Two hours of nonstop eating and learning? Sign me up!

Explore Chicago on Segway, Bus, and Kayak Tours

#7 Glide Through Town on a Chicago Segway Tour

chicago segway tours

Photo Source: City Segway Tours Chicago

If you’re not self-conscious about wearing a helmet, Segway tours are an amazing way to see Chicago.

City Segway Tours offers especially wonderful Segway tours of Chicago that begin at the south end of Grant Park and stop at historical highlights including the Field Museum and other Museum Campus sights, Buckingham Fountain, and Soldier Field.

These tours boast groups of less than 8, so you’ll have plenty of opportunities to ask questions about the stops on your Segway tour — and you won’t risk colliding with another rider during your experience.

#8 Feel the Wind in Your Hair on a Chicago Bike Tour

chicago bike tours

Photo Source: Choose Chicago

With more than 200 of miles protected, buffered, or shared bike lanes (including the nearly 20 mile lakefront path), Chicago is one of the best cities in the United States for cyclists. And plentiful bike parking means it’s easy to hop off and hop back on when you’re seeing the sights from a bicycle.

Why should you care?

Bike and Roll Chicago offers four Chicago bike tours that focus on different aspects of the city, including its Friendly Neighborhoods Tour, which takes participants out of the most crowded tourist areas and into beautiful nearby neighborhoods like Old Town, the Gold Coast, and Lincoln Park.

#9 Let Someone Else Do the Driving: Chicago Bus Tours

Chicago bus tours big bus

Photo Source: Visit The USA

Let’s face it:

Chicago is a big city. If you’ve only got a short time to see a lot — or you just like riding high while somebody else does the driving — then a Chicago bus tour is your best bet to check out the city.

Why settle for taking the bus from Point A to Point B when you can use it to zig-zag all over town?

Big Bus Chicago offers its signature “Hop On, Hop Off” Chicago bus tours to allow riders to play tourist on their own terms. Big Bus’s route has 14 stops throughout the Loop, including Buckingham Fountain, the Willis Tower, and Water Tower Place. Buses arrive every 30–45 minutes, ensuring you’ve got plenty of time to explore before you jump back on the bus to see more of the city.

#10 Grab Your Paddle for a Chicago Kayak Tour

chicago kayak tours

Photo Source: Wateriders

The Chicago River offers unique vantage points that no land-based tour can offer.

Veteran tour operator Wateriders has been around since 1997 and has hosted more than 100,000 enthusiasts on its many tours. Try a Sunset Paddle or Moonlight Paddle for a relaxing evening activity that lets you see the city all lit up at night from your private kayak.

Worried that you’re not ready to take off in your own kayak?

Wateriders offers an “on-land” lesson to everyone who books a tour, and all leaders are also experienced kayakers who will lend a helping hand to nervous tour participants who don’t quite have their sea legs.

Have We Mentioned Chicago’s Food + Tour Scene?

#11 Nosh Your Way Around Town With a Chicago Culinary Tour

chicago food tours

Photo Source: Chicago Food Planet

No list of the best Chicago tours would be complete without a mention of the city’s phenomenal food scene. Whether you love a classic Chicago dog, love to splurge on Michelin-starred cuisine, or will travel to the far corners of the city for the best al pastor taco in town, you’ll never be without inspiration for your next meal here.

Chicago Food Planet offers Chicago food tours all over the city — they pioneered the perfect culinary tours back in 2006 and haven’t looked back since.

How do they work?

You’ll meet up with one of Chicago Food Planet’s experienced tour guides, get a preview of what’s ahead during your tour, then set off on foot for a culinary scavenger hunt in the city’s hottest neighborhoods trying all the Chicago-style classics along the way, including hot dog, deep-dish pizza, and Italian beef sandwiches.

Heading out on a tour?

No need to pack a snack. All your food is included — and you’ll never leave hungry.  Locals and tourists alike love these tours because you’ll go behind the scenes and meet the culinary artisans at the hot spots you’ve read about, as well as the artisan mom-and-pop shops you always wondered about, from authentic dim sum and a taste of Szechuan cuisine on the Chinatown Adventure to a sampler of the classics on our Best in Chow tour.  

INSIDER SCOOP: Want to visit Chinatown but not sure where to eat, what to do or when to go?  You’re in luck- check out our Chinatown Chicago: 22+ Best Restaurants and Things To Do Guide and you’ll be able to traverse Chicago’s Chinatown neighborhood like a seasoned local.

#12 Slosh Along on a Chicago Beer and Brewery Tour

chicago brewery tours

Photo Source: Moody Tongue Brewery

In December 2018, Chicago became the city with the most brewers (167!) within city limits — beating out Denver, Seattle, Portland, and San Diego for top honors.

Why is that important?

If you’re a beer lover, there are plenty of Chicago brewery tours to wet your whistle and give you a great taste of what the city has to offer.

#13 Get Down With Daisy Cutter at Half Acre Brewery

Brew and Grow Beer Making Classes

Photo Source: Brew & Grow

Headquartered in Chicago’s homey North Center neighborhood, Half Acre is famous for its Daisy Cutter IPA. The brewery now has two facilities, including a production line just north in the Bowmanville neighborhood, and both locations offer brewery tours.

Tours of the North Center facility — which has an adjacent taproom offering fantastic nachos, among other items — are held every Saturday, and the Bowmanville facility has a tour one Sunday per month.

#14 Check Out Lagunitas Brewery, Our Favorite California Transplant

chicago lagunitas brewery tour

Photo Source: CNBC

The uber-popular West Coast transport Lagunitas opened its Midwest hub in spring 2014.

Want a tour?

Head southwest of the city to the Lawndale neighborhood for a Lagunitas Chicago brewery tour — they’re offered “every freakin’ day,” according to the website. Don’t forget to wear your FitBit if you take the walking tour, and if you’re thirsty, sign up for the tasting tour (offered at 1 and 3 p.m. Monday through Friday). Stick around for delicious food and music from local artists in the on-site taproom.

#15 Sip Culinary Brews at Moody Tongue Brewery

chicago brewery beer tours moodys

Photo Source: Time Out Chicago

Trek down to the Pilsen neighborhood for a tour of Moody Tongue’s facility that produces locally renowned, chef-inspired beers like Caramelized Chocolate Churro Baltic Porter. Tours are offered throughout the afternoon on Saturdays and Sundays — or, if you’re feeling extra fancy, you can schedule a beer and cake pairing experience featuring the taproom’s 12-layer German chocolate cake.

#16 Take a Deep Dive Into Chicago Deep Dish Pizza — And More

chicago pizza tours

Photo Source: Time Out Chicago

It’s no secret:

If Chicago is known for one type of food, it’s Chicago-style pizza — which Lou Malnati’s perfected decades ago. But there’s so much more to the Windy City’s pie scene than just deep-dish pizza. Chicago pizza tours will give you a well-rounded (couldn’t help it) taste of all the different styles and flavors of pizza this diverse city has to offer.

Chicago Pizza Tours offers three unique tasting excursions, including The Original Chicago Pizza Tour, which transports attendees all over the city in a comfy tour bus to visit 10 pizza landmarks, including Pequod’s, Coalfire, Pequod’s, and Spacca Napoli.

You full yet?

See What Chicago’s Made of on a Chicago Architecture Tour

Chicago is home to the best architecture in North America. Period.

So:

If you always find yourself looking up and wondering, “What is that building?” while visiting a new place, then Chicago’s world-class architecture will stop you in your tracks. Take advantage of one of the many available Chicago architecture tours during your visit with our list below.

#17 Find Inspiration On a Chicago Architecture Foundation Tour

chicago architecture tours

Photo Source: Flickr

The Chicago Architecture Foundation’s mission is “to inspire people to discover why design matters” — and it offers many tours to residents and visitors alike in service of that mission, led by knowledgeable docents who really understand the city’s iconic buildings.

The foundation offers Chicago boat tours, walking tours, and bus tours for enthusiasts of all levels of ability, including a fast-paced 90-minute “Must-See Chicago Tour” that uses Chicago’s “L” trains to transport attendees from sight to sight.

Why does this matter?

Because Chicago architecture can feel intimidating, but this outfit does a solid job of helping you become an architecture junkie for life.

#18 See History Up Close With a Frank Lloyd Wright Tour

chicago frank lloyd wright tours

Photo Source: @flwtrust

Architecture buffs know Chicago is home to many homes designed by Chicago architect Frank Lloyd Wright. The Frank Lloyd Wright Trust offers a variety of tours to view the famed architect’s creations from Oak Park to Hyde Park — including an annual Wright Plus Architectural Housewalk in the spring.

True devotees will love the free Frank Lloyd Wright Trail, a self-guided adventure tour with 13 stops highlighting some of the architect’s most famous works, including The Rookery in the Loop, and the Unity Temple, Wright’s first public commission.

Sun-Soaked Chicago Summer Tours for da’ Summer Days

From Cubs games to al fresco dining, Chicago puts on its best show for tourists and residents alike during the summer months.

Let’s be honest:

You can’t go wrong with any Chicago tour in the summertime, but it’s really the best time to get off the beaten path and truly explore Chicago with the ideas we’ve curated below.  And if this list still isn’t enough, be sure to check out our 18+ Best Summer Chicago Things to Do guide for even more ideas and options.  

#19 Hit a Home Run With a Wrigley Field Tour

chicago wrigley field tours

Photo Source: Wikipedia

Many North Siders will tell you there’s nowhere better during summer in Chicago than at Wrigley Field. Get a behind-the-scenes, 75- to 90-minute guided Wrigley Field tour that includes everything from the press box and Chicago Cubs’ own dugout to the famed field itself.

You never know when they’ll win the World Series again, so best to visit sooner rather than later!

#20 Get Weird With Offbeat Chicago Tours

chicago bizarre bucktown tours

Photo Source: @bizarrebucktown

Need a summer-day activity on the cheap?

Bizarre Bucktown, creator of irreverent tours of neighboring ‘hoods Bucktown and Wicker Park tours, has just the thing: a free, self-guided tour of The 606.

Also known as the Bloomingdale Trail, The 606 is an elevated walking path cuts through chic, spendy Bucktown (located just northwest of the Loop) and west toward the historically Hispanic Humboldt Park. It’s a haven for joggers and cyclists, and offers plenty of opportunities to head back to street level and explore the surrounding neighborhoods.

Thaw Your Boredom With Chicago Winter Tours

Here’s the deal:

Chicago is a city for winter warriors! Visitors to our fair city in the coldest months, of the year, notably December, January and February, typically face smaller crowds and shorter lines — and get to see how magical Chicago can be during the winter.

We’ve listed below a few excellent ideas to explore Chicago during those short winter days:

#21 Explore Underground on a Chicago Pedway Tours

chicago elevated tours

Photo Source: Chicago Elevated

Did you know Chicago has an intricate system of underground walkways designed to keep commuters snug and warm during cold and inclement weather?

Intrepid tour guide Margaret Hicks of Chicago Elevated offers award-winning Chicago pedway tours to explore the system that covers more than 40 city blocks and connects more than 50 buildings.

Get on her level!

#22 Get Cozy With an Indoor Navy Pier Food & Culture Tour

navy pier chicago winter summer tours

Photo Source: Navy Pier

Not all of Chicago Food Planet’s Chicago food tours require a coat during the winter — on the Signature Food Tour of Navy Pier, you’ll taste three iconic Chicago dishes (plus some new favorites) without leaving the building!

Learn their histories and sample Giordano’s Pizza, Garrett’s Popcorn, America’s Dog and much more, all while whetting your appetite with some impressive culture and history while you’re at it.

Win-win.  

INSIDER TIP: No trip to Chicago is complete without a stop at the city’s iconic Navy Pier.  If you’re looking for additional insight into all-things Navy Pier, we recommend reviewing the 27+ Best Navy Pier Chicago Things to Do & Restaurants guide to help in your planning and strategy.

#23 Soar Above the City on a Chicago Helicopter tour

chicago helicotpor tours

Photo Source: @ctopphotos

Looking for a bit more of a thrill as you explore the city? Hop into one of Chicago Helicopter Experience’s luxury aircraft for a Chicago helicopter tour.

Strap in and get this:

Chicago Helicopter Experience, the city’s only FAA-certified helicopter tour and transportation company, offers several tours in their helicopters that seat up to six riders, including the City Lights Tour, a live-narrated tour that offers breathtaking panoramic views of the Chicago skyline after dark.

These helicopter tours of Chicago aren’t cheap — but when’s the last time you flew in a helicopter?  We say go for it and you won’t be disappointed.

#24 Snap Your New Profile Pic on a Chicago Photography Tour

chicago photography tours

Photo Source: PxHere

For some travelers, an Instagram full of blurry selfies isn’t enough to remember an unforgettable journey. For passionate hobbyists and more professional photographers alike, Chicago photography tours are the way to go.

Want to know the best part?

Teresa Peek, founder of Tour Through a Lens (TTAL), creates customized private tours for every customer focused on taking captivating photos geared toward their personal interests. TTAL offers only one public photo tour, a 2.5-hour photography tour of Chicago’s alleys with the perfect light and shadow play for dramatic photographs.

#25 Channel Your Inner Capone With a Chicago Gangster Tour

chicago gangster tours

Photo Source: Yelp

Untouchable Tours, which claims to be the original Chicago gangster tour, promises its participants nothing less than a “bang-up” time. Aboard a branded black bus, participants are taken back in time to Prohibition-era Chicago by local Chicago tour guides who take on the personas of 1920s gangsters themselves.

Untouchable’s tours focus on gangsters like Al Capone, Bugs Moran, and John Dillinger — with stops at the former Biograph Theatre and Holy Name Cathedral, to name just a few.

Maybe along the way, you’ll find out why they really call Chicago the Windy City. (Hint: It ain’t the lake breeze.)

Connect With Chicago Food In Unexpected Ways


Enjoy the Best in Chow Food Tour on TripAdvisor’s #1 Rated Chicago Activity.

Skip the lines & eat iconic Chicago-style dishes in River North and Streeterville.

Offered daily; Includes Chicago-style hot dog, Italian beef and deep-dish. 


$60 Adult Tickets (Food Included)
VIP Tickets Available (+ Drink Pairings)

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