The Best 9 Tours in Chicago You Don’t Want to Miss

Looking for the best tours in Chicago? We've got you covered.

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What’s not to love about Chicago? Travelers who love great food, skyscrapers, the beach, quirky tours, and fascinating history will find something to love during a trip here.

If you didn’t already know — This is the city of the Great Chicago Fire, mobsters and conspiracies, prohibition, and deep-dish pizza!

Whether you want an exciting thrill ride, to learn history, try unique foods cocktails, enjoy stunning views or combine them all…Chicago has options for you.

Today we’ll share with you our list of the best tours in Chicago:

Best Bus Tour: Chicago Crime and Mob Tour

This is one of those tours you’ll end up talking about a lot when you return home.

The tour is rich with exciting stories about the darker figures in Chicago history like John Dillinger and Al Capone.

Al Capone Chicago Crime and Mob Tour | Photo via

One of the other mobsters you’ll learn more about is Frank Nitti. Though he was known as “The Enforcer”, one of Chicago’s most famous gangsters used soldiers for his crimes instead of performing them himself.

How did he gain his position in Chicago’s North Side Gang?


This is exactly the kind of story you’ll learn more about on this tour. You’ll take a bus around the city with stops off and on at historic crime scenes.

People love this tour for the great information and knowledgeable tour guides.

Best dinner cruise: Chicago Sunset Dinner Cruise

You want to see as much as you can while you’re visiting a city, but you also want to kick back and relax when you’re on vacation. Solution? A dinner cruise.

girlfriends taking a picture on a dinner cruise

Chicago Sunset Dinner Cruise | Photo via

One of the best Chicago boat tour options out there includes catching the sunset on Lake Michigan while enjoying an all-you-can-eat-buffet on the water.


This cruise comes with a live DJ and interactive games for on-board entertainment. In the summer, you can upgrade to a fireworks cruise.

The staff is known for being very friendly and accommodating. The views from the deck are stunning and the sunset is spectacular. Also, buffet and food options are tasty.

Best night tour in Chicago: Chicago Segway Night Tour

Couple at night riding a Segway

Chicago Segway Night Tour | Photo via

Don’t miss out on seeing Chicago’s famous landmarks lit up at night.

On this Segway tour, after a brief orientation session, you travel along the shore up to the big must-see nighttime landmarks like Navy Pier and Buckingham Fountain.

When you take a Segway tour, you get the independent mobility you’re missing on a bus tour, but cover more ground than walking, all while being an eco-friendly choice. Plus, Segways are just more fun!


Consider doing a tour at night too.

Best Aerial Tour: Chicago Helicopter Tour

Couple looking over the city inside helicopter

Chicago Helicopter Tour | Photo via

Do you want to see Chicago in every possible way you can?

Get ready to see it in a way that few who live here ever get the chance with a helicopter tour. This is one of the top tours in Chicago and perhaps a bucket list item for many

The company is known for having a friendly and fun staff, including the pilots. The tour itself is brief but unforgettable. You’ll be surprised by how different the color of Lake Michigan is from up above.

They do tours at different times of day, including evening “Golden Light” tours where you can watch the sunlight dim over the city.

Best Walking Tour: Historic Skyscrapers Chicago Walking Tour

Inside of The Rookery

The Rookery | Historic Skyscrapers Chicago Walking Tour via

In 1871, the Chicago fire destroyed much of the city. In the years following, Chicago shaped the history of what skyscrapers would eventually become as the city rebuilt.


Many of Chicago’s great buildings were built between the 1870’s and the 1930’s. This is before the time of the cranes we use today. These buildings took longer and were more dangerous to build than anything we’d do today, and that means they have stories.

This is one of the best Chicago walking tours for taking a closer look at the skyline you see in every Chicago postcard.

Your tour guide, a trained expert from the Chicago Architecture Foundation, will take you through the Historic Chicago Loop and tell you stories about the buildings and the people who created them.

Best Food Tour: Famous Tastes of Chicago Food Tour

Guy and a girl eating a Chicago's famous hotdogs

Famous Tastes of Chicago Food Tour | Photo via

We all know that food is an essential part of a city’s culture, right? Is there any better way to get to know a place than by eating? Chicago has diverse neighborhoods with a lot of food options, so it would be a shame to miss out on one of the best Chicago food tours to help you try as much as you can.

On this tour, they’re really hoping to give you a chance to get to know Chicago through food.

This is a three-hour walking tour that includes interesting information on Chicago’s history, food, and architecture, all while you eat.

People who love this tour come away talking about the great tour guides and whichever foods were their favorite, from the German sausage to the Italian beef sandwich, and of course, the Chicago deep-dish pizza.

Make sure to come hungry! You will not be disappointed with the food included on this tour!

These tours leave at 11:00 am, so if you’re a breakfast person, keep it light.

Best Architecture Cruise: Lake Michigan & Chicago River Architecture Cruise

People listening to boat tour guide while looking at Lake Michigan

Lake Michigan & Chicago River Architecture Cruise | Photo via

Do you just love the view of Chicago’s skyline from the water? Get to know the stories of this skyline with the best architecture tour Chicago offers.

One thing that makes this tour special is that you have the opportunity to board two different boats.


You’ll cruise along the Chicago River on a riverboat, traveling through the city and passing through the Chicago River Locks while you take an up-close look at the buildings. You’ll also hop on a speedboat to take a look at the skyline from Lake Michigan.

Rest your feet, learn about the city’s architecture, and have fun experiencing two different boating experiences in one tour.

Best Bar Crawl: Chicago Prohibition Tour

Friends dressed up enjoying themselves at Chicago Prohibition

Chicago Prohibition Tour | Photo via

Gangsters? Politicians? A battle for your right to Happy Hour? This isn’t the history lesson you sat through in high school.

Sip your way through famous Chicago speakeasies while a tour guide tells you the stories of this brief time in Chicago when the government said “No drinking!” and the people said “Huh? I can’t hear you.”

This tour is four hours long. A bus will transport you between locations.

The tour guides here are very knowledgeable and can teach you a thing or two in so little time!

Best Bike Tour: Chicago Lakefront Neighborhoods Bicycle Tour

Group of people riding by Chicago's Lakefront Neighborhoods

Chicago Lakefront Neighborhoods Bicycle Tour | Photo via

This tour comes highly recommended by many travelers!

Chicago’s Lakefront neighborhood is not to be missed. This bike tour has been recognized with a few different awards from travel companies over the years, including the best sightseeing tour of 2018 by TripAdvisor.

This tour takes you away from the major sightseeing spots and gives you a feel for the city parks, neighborhoods, and beaches the people of Chicago call home.

The tour guides here are knowledgeable,  fun, and quite entertaining as well!

This wraps up our list of the best tours in Chicago… We hope you try at least one of them on your visit to this great city!

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