Chicago, Illinois is famous for its amazing deep-dish pizza, beautiful architecture, gorgeous waterfront, and unique history. It’s also one of the top tourist destinations in the Midwest and it’s no surprise why! The city has a ton to offer visitors whether you’re interested in culture, sports, outdoor activities, or nightlife.
We know that it can be a bit confusing to know where to even start when you’re planning a visit to a city with so many options so to help you get started, we have created this list of the top tours and activities to do in the Windy City.
So Many Ways to See Chicago
If you’re planning a trip to the Windy City, you can’t go wrong with scavenger hunt tours by Let’s Roam! These walking tours in Chicago are app-guided, and there are options to suit any traveler. From family-friendly sightseeing experiences to adult-oriented pub crawls, there’s no shortage of fun!
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The Best Excursions and Tours in Chicago
Below you’ll find a list of the best tours and excursions to do in Chicago. This is based on the experience of our own in-house travel experts as well as TripAdvisor and Google Map reviews. Some of them are walking tours while others rely on buses to get around. There are also a few that are adults-only so you may want to skip on those if you’re traveling with the kiddos!
Disclosure: All of the tour departure times and locations were correct at the time of writing however, it’s important to double-check the information before heading out for the tour as these may change, especially if COVID restrictions are put back in place.
Chicago Walking Tours
With its grid-like streets and lovely Riverwalk, Chicago is a fabulous place for walking. Combine this with the show-stopping architecture and the engrossing history and you have all the ingredients that you need for days spent exploring the streets. While it’s great to stroll along on your own, a sightseeing tour of the city will let you see a whole different side of a city and help you learn the finer details of what makes the city tick. It’s great to do one at the start of your visit as your tour guides can give you great insight into some of the best places to go for dinner or drinks after the tour and if you’re traveling on a budget, you may learn some great money-making tips!
1. Riverwalk & North Loop Tour
Run by Free Chicago Walking Tours, this two-hour walking tour gives an in-depth look into the history of Chicago going all the way back to the late 17th-century until today. The tour covers everything from the role that Chicago played in the Revolutionary War to the Roaring 20s and as you stroll through the Loop, you’ll see the Chicago River, Daley Plaza, the Chicago Cultural Center, and more. The tour is on a pay-as-you-wish basis so you can be sure that the guides will work hard for their money!
2. Let’s Roam Chicago Sightseeing Scavenger Hunts
Here at Let’s Roam, we think one of the best ways to get to know a city is through a destination scavenger hunt! On this intriguing Chicago Loop hunt, you’ll be asked fun trivia questions about some of Chicago’s top attractions including The Bean, the Art Institute of Chicago, the Crown Fountain, and the world-famous Tiffany Dome. You’ll also have plenty of prompts to take great photos to remember your trip by! You’ll learn a lot about Chicago’s storied buildings and epic sculptures!
Once you have finished up with the Loop hunt, don’t forget to go back and do the Magnificent Mile Scavenger Hunt to see sites like Washington Square Park, the Tribune Tower, and the Wrigley Building. Both tours take around an hour and can be conveniently done on your smartphone using the Let’s Roam app.
3. Chicago Gangsters and Ghosts Tour
After seeing Chicago’s famous attractions, it’s time to go into its underbelly and learn about the gangsters that used to rule this joint. Chicago is infamous for its gangster past and during the 1920s and 1930s, mobsters were in control of much of the city. 100 years ago, murder and mayhem lurked in the shadows, and today, you can hear all about the men (and women!) that left their mark on Chicago.
This fascinating (and occasionally bone-chilling Chicago Gangsters and Ghosts Tour is a two-hour-long affair that takes you through the Chicago Loop Vice District, stopping by the Congress Hotel, Death Alley, the Palmer House, and many other creepy places. Rather than being a theatrical display, the guides tell the stories in a somber, delicate way that makes it easy to understand the impact that the mobs had on the psyche of the city. Tours leave throughout the day with three daytime tours and one evening tour and you can book tickets online.
4. Dazzling Interiors of the Loop
Chicago is well known for its interesting blend of architectural styles and people around the world can easily identify its skyline. However, few people get a chance to see some of Chicago’s most striking Interiors and Inside Chicago’s Walking Tours wants to change this with their two-hour-long Dazzling Interiors Tour. During the tour, you’ll get a chance to see the remarkable interiors hidden behind some of Chicago’s most famous facades. Some of the highlights of the tour are art-deco lobbies, gilded ceilings, and early designs by master architect Frank Lloyd Wright. Tours cover just one and a half miles so they are suitable for people of all ages and this is the perfect way for art lovers to get an in-depth look at some of Chicago’s most distinctive buildings.
5. Off the Grid Tour
Offered by Free Chicago Walking Tours, a pay-as-you-wish tour operator, the Off the Grid Tour veers off the standard tourist route and visits some of the city’s most Instagrammable spots including Death Alley, the Chicago Cultural Center, and the Pink Flamingo Wall at Flamingo Rum Club. The tour starts at the ACME Hotel in the River North before leading you through the Loop where you can get photos in front of Chicago’s most recognizable landmarks before finishing up the world’s largest Tiffany Glass Dome.
The Off the Grid tours are only held sporadically throughout the year so if you aren’t able to join one—don’t worry! There are still plenty of other free walking tours to choose from including the Loop Interior Tour, the Crime & Gangster Tour, the Millenium Park Tour, and many more. Take a look at their website for more information.
Bike and Segway Tours
Walking is one of our favorite ways to explore a new destination but, sometimes, having your own set of wheels. Bike and segway sightseeing tours let you explore a city at a quick pace while staying having the time to soak up the atmosphere.
6. Bikes, Bites & Brews Tour
What better combination can there be than biking, beer, and bite-sized treats. During this four-hour tour led by Bobby’s Bike Hike Chicago, riders will cover a whopping 13 miles across Gold Coast, Lakeview, Lincoln Park, and Wrigleyville, making perfectly timed pit stops along the way where they can give their taste buds a workout with pizza, hot dogs, cupcakes, and, of course, beer.
The wonderful guides and the long route make this the perfect introduction to the city and lets visitors cover an impressive amount of ground in a short period of time. The cost of the tour includes bike rental, food, and drinks and riders must be at least 21 years old. If you would like to go on a family-friendly version of the tour, they also offer Bobby’s Bike Hike Chicago’s Family Food & Bike Tour. If you love biking, this is one tour of Chicago that you won’t want to miss!
7. Chicago Lakefront Segway Tour
With its relatively flat terrain and sweeping lakefront, Chicago is a fantastic city to explore by segway. Absolutely Chicago Segway Tours gives travelers the opportunity to zoom by some of the city’s most iconic attractions including Millennium Park, Monroe Harbor, and Museum Campus, home to the Shedd Aquarium, Soldier Field, the Field Museum, and much, much more on this eight-mile-long adventure. Tours last roughly two to two and a half hours and the insightful and entertaining tour guides along with the thrill of riding a segway will make the time go by in a blink of an eye. Absolutely Chicago has a wide range of tours covering different areas of the city as well as themed tours like the Chicago Mob and Gangster Tour and a chilling ghost tour.
While we love the idea of going on walking tours, sometimes the weather (or our bodies!) just isn’t cooperating with us and it’s time to join one of Chicago’s many bus tours. If you’re tight on time, bus tours are a great way to see many different areas of the city or if you have a bit more time to spare, they are a great way to discover the neighborhoods that you want to go back to!
8. Hop-On Hop-Off Bus Tour
It can be a bit challenging to plan a trip full of exciting sightseeing adventures (trust us, we know!) but Big Bus makes it easy to get a great overview of Chicago without even having to leave the comfort of your bus seat (but it’s much better if you do!). These useful bus tours allow passengers to get on and off as often as they wish at one of the conveniently located stops. This allows you to see the things that you want but skip the things that you aren’t interested in. Most tour packages are good for one day (roughly eight hours) and it’s possible to “upgrade” your ticket to include extra activities or even extra days. Expert tip: Keep a close eye out for the bus signs or make a mental note of where you got off the bus as they can be really hard to see at a few of the attractions.
9. See It All Minibus Tours
If you love the idea of a bus tour but aren’t sure that the hop-on-hop-off buses are right for you, you may want to consider one of the See It All Minibus Tours. During the tour, you’ll be whisked around downtown and the north side of the city in a climate-controlled minibus, passing by the Loop, Millennium Park, the Buckingham Fountain, the Wrigley Building, the Chicago River, Lincoln Park, and even the Original Playboy Mansion.
There is an entertaining narration that plays throughout the journey telling you about the city’s long history and colorful characters and you can hop out and take photos at four designated photo stops along the way.
If you want to keep the fun going after the tour, you can add on a Chicago River Architecture Boat Tour.
10. Family Secrets Bus Tour
If you want to get an inside look at a modern-day Soprano-like organized crime family, this unique tour can take you deep into the world of the mafia. The Family Secrets tour is run by Frank Calabrese Jr. who once worked as a soldier in his dad’s Chinatown crew. During the two-hour bus tour, he gives an unfiltered, firsthand account of life in the mob by telling stories of the drama and endless killings that he witnessed. He takes you to actual crime scenes in the areas where the Chicago Mob once worked, lived, and played. Private tours are available throughout the week and begin outside of the Chicago Chop House on West Ontario Street.
11. Chicago Crime and Mob Bus Tour
Organized by Chicago Crime Tours and Experiences, this crime-themed two-hour-long bus tour gives visitors the chance to go deep into the world of Al Capone, John Dillinger, and The Untouchables, who ultimately brought them down through a series of stops at well-known crime sites, including the site of the infamous Valentine’s Day Massacre, and the courthouses where the city’s most prolific criminals had to stand trial for their crimes. While their signature tour is offered during the day, there is also a two-and-a-half-hour-long nighttime tour that puts everything in an even darker light!
Food Tours and Bar Crawls
Here at Let’s Roam, two of our favorite pastimes include eating and touring so food tours are one of our must-do activities wherever we go. Food tours are an amazing way to not only try some hidden culinary gems but they are also perfect for learning more about some of the off the beaten track parts of a city.
12. Gateway to the West Loop Food Tour
With a slew of mouth-watering delights hidden in eateries all across the city, it can be tough to know where to go for the best eats in the Windy City. Chicago Food Planet’s three-hour-long Gateway to the West Loop Food Tour helps you get your hands on some of the best dishes that the city has to offer ranging from pizza to doughnuts. Throughout the tour, you’ll learn insider information about the history of both Chicago and the West Loop and your guides will be more than happy to impart some local wisdom. Make sure to come hungry as they give out some hefty portions during this tour.
If you’re blown away by this tour, they also have a food tour of Chinatown.
13. Original Chicago Pizza Tour
If there is one food that you absolutely must try in Chicago, it has to be the deep dish pizza. On this tour led by Chicago Pizza Tours, you’ll get to visit some of the city’s most beloved, independently-owned pizzerias. The tour includes six or more slices of pizza (wow!) and the guides are informative and fun and will teach you about a lot more than just pizza which makes it well worth the money. They offer bus tours and walking tours so it’s perfect for people with mobility issues and if you want to make it a bit more festive, you can opt for the Chicago Pizza and Cocktail Tour.
14. Taste of Chicago Food Tour
This is another food tour that’s sure to please even the pickiest of eaters. Run by Tastebud Tours, this appetite extravaganza takes you through Chicago’s downtown Loop stopping at many of the area’s most popular eateries to try the deep-dish pizza, sandwiches, and desserts. The tour guides will point out some of downtown’s most important attractions on the way and will impress you with this encyclopedic knowledge and endless enthusiasm.
15. Historic Chicago Walking Bar Tour
History lovers who want to learn more about the Prohibition era can join this part-history tour, part-bar crawl offered by the team at Chicago Detours. During the two-and-a-half-hour tour, you’ll visit some of Chicago’s most historic bars and pubs including a Jazz Age Hotel and the Billy Goat Tavern, located inside a 19th-century mansion.
If you’re looking for another off-beat tour, Chicago Detours also runs an 1893 World’s Fair Tour and a Chicago Neighborhoods Tour that takes you into the north, west, and south sides of the city and includes a stop in a neighborhood dive bar and the opportunity to dine at a home-style Polish restaurant. Yum!
16. Chicago Prohibition Bus Tour
This bus tour is certainly unique! The three-and-a-half-hour Chicago Prohibition Bus Tour visits four former speakeasies where you can learn about this eventful period in Chicago’s history including the types of drinks that people would have ordered when they strutted up to the bar. All of the stops on the tour are very different so you don’t need to worry about things feeling repetitive and the smooth-talking guides help move the evening along nicely. If you want to get some exercise, there is also a walking version that lasts two and a half hours.
17. Chi-town Bar Crawl Scavenger Hunt
If you want a unique take on the standard bar crawl, the Let’s Roam’s Chi-town Bar Crawl may be right up your alley! Here, you can battle your closest friends and drinking buddies to crazy challenges until one of you is the champion of Chi-town. The challenges go from easy-peasy to difficult and are perfectly designed to bring out your competitive side and you may even discover a new favorite hangout or rediscover your old stomping grounds. While the hunt normally takes around one and a half to two hours, you can make it as long or as slow as you want!
Between the enormous and sparkling Lake Michigan to the quaint and charming Chicago River, Chicago is a watery city so it probably comes as no surprise that one of the best ways to explore is by boat! Luckily, there is a huge array of sightseeing cruises to choose from and virtually all of them will give you great views. Just keep in mind that Chicago has earned the nickname the Windy City for a reason and umbrellas may not be the best things to use as rain cover if you’re going on a boat tour. It is a good idea to pack a waterproof jacket or a poncho with you just in case!
18. Chicago Architecture Foundation River Cruise
This special architecture cruise takes visitors along the Chicago River while expert volunteer docents tell them the inside scoop on 50 of Chicago’s most notable buildings. The Chicago Architecture Foundation’s River Cruise uses the fleet of Chicago’s First Lady Cruises for these 90-minute tours which means that you’re in the hands of professional staff and have access to full-service bars and open-air upper decks that are the perfect spot to get some great photos. There are daytime and nighttime sailings and, for just about $5 more, you can also visit the Chicago Architecture Center.
19. Chicago Sunset Cruise
This relaxing cruise run by Wendella Tours and Cruises is one of the best ways to finish off a long day of sightseeing. During the 90-minute cruise on Lake Michigan, you’ll watch as the sun sets behind the city skyline and turns the sky into a swirl of pink, orange, and red. The cruises have a full bar where you can purchase drinks and snacks and there is a climate-controlled lounge area that keeps you warm in the winter and cool in the summer. The cruises leave from Michigan Avenue. The departure times vary throughout the year so make sure to check their website for the most up-to-date information and to book tickets.
If you want something a bit shorter or only have time during the day, they also offer a 45-minute architecture tour on the Chicago River. This tour will highlight some of the most famous Chicago landmarks and you can learn a lot during a short period thanks to the informative guides!
20. Historic Chicago Tour
Run by Urban Kayak Chicago Riverwalk, the Historic Chicago Tour gives you a “duck’s” view of the beautiful Riverwalk as you paddle down the Chicago River. Along the way, you’ll stop at key points to learn more about the area’s history and architecture. Although there is a bit of boat traffic along the river (OK, a lot of boat traffic), the guides know how to keep everyone safe and it’s appropriate for even beginner kayakers. If you prefer to go it alone, Urban Kayak also rents kayaks and paddleboards and offers classes to help you up your paddling skills.
21. Skyline Lake Tours
With unparalleled views over Lake Michigan and the city skyline, Shoreline Sightseeing Skyline Lake Tours offers breathtaking, 40-minute cruises covering six miles of the shoreline. Some of the highlights of the tour include the Willis Tower (home of the Skydeck Observation Deck and formerly known as the Sears Tower), the John Hancock Center, the Field Museum, and the Adler Planetarium. There is a bar on board to buy drinks and a pre-recorded track of interesting information playing throughout the ride. While this is a more general tour, they offer an architecture tour, as well.
Tours depart from Navy Pier on the half-hour, with extra cruises sometimes added in spring and fall. Excursions are dependent on weather, so be sure to check times and availability before you go. Generally, there are no tours during colder months of the year.
22. Chicago Skyline Sail
There is something truly special about sailing. From the wind rushing through to sails to the sound of the waves lapping against the boat, it’s a relaxing experience and a great way to explore Lake Michigan. Tall Ship Windy (love the name by the way) offers a Skyline Sail onboard a 148-foot four-masted schooner. You can get sweeping views of the Chicago skyline from the deck of the boat during the 75-minute ride and the soaring skyscrapers create a mesmerizing juxtaposition to the traditional sailboat. If you’re traveling with kids, make sure to check their list to see if they have any of their pirate-themed outings or fireworks cruises while you’re in town!
23. Seadog Lakefront Speedboat Tour
While sailboats and cruises are a great way to get out on Lake Michigan if you’re in the need for speed look no further than the Seadog Lakefront Speedboat Tour operated by City Cruises by Hornblower. As you whiz across the lake during this 30-minute ride, you can absorb the skyline views while you listen to the guides give vivid and entertaining descriptions of what you’re seeing. Keep in mind that the boat is open-air, so you might get wet, and it’s probably best to avoid it during rough weather.
If you want to zip across the lake even faster then you can opt for their extreme thrill ride. Conversely, for a more leisurely option, you can opt for a brunch, lunch, or dinner cruise or try one of their special holiday-themed boat rides. There are plenty of options to choose from so it’s a good idea to check out their website before deciding on a tour.
Ready to roam?
We hope that this list of the top tours and excursions in Chicago has left you inspired to pack your bags and head to the Windy City for your next vacation. If you need more expert advice, make sure to check our lists of the Best Things to Do in Chicago and the 25 Best Day Trips From Chicago, or download our app and try any of our Chicago scavenger hunts.
As always, we would love to hear your feedback and please let us know if we have missed any hidden gems!
Frequently Asked Questions
What are the best walking tours in Chicago?
Some of the most popular walking tours in Chicago include options from Free Chicago Walking Tours, scavenger hunt tours from Let’s Roam, and the Chicago Gangsters and Ghosts Tour.
What are some tours that you must do in Chicago?
If you’re planning some sightseeing in Chicago, don’t miss out on the intriguing crime tours, and be sure to hop on a boat cruise. Lastly, try at least one of the app-guided scavenger hunt tours from Let’s Roam!
What are the best Chicago boat tours?
There are many great boat tours in Chicago, including the Chicago Architecture Foundation River Cruise, the relaxing sunset cruise from Wendella Tours and Cruises, and the Urban Kayaks’ Historic Chicago Tour.
What are the best pub crawls in Chicago?
The Windy City is full of amazing pubs and grub! If you’d like to tour Chicago pubs, try Let’s Roam’s Chi-town Bar Crawl, the Chicago Prohibition Bus Tour, or the Historic Chicago Walking Bar Tour.