The glittering facades of the buildings in Chicago are rivalled only those by New York! One of the largest cities in the USA, Chicago offers everything that a metropolis offers and more.
With a history dating back almost two centuries, Chicago has grown from a trading post near the Great Lakes to the third-most populous city in the USA. It has undergone phases of transformation, including a terrible fire in 1871 and it rose like phoenix becoming one of the most important industrial, financial, and business hubs of the world. It also has a sinister past replete with mafia and gangsters!
Today, the city is vibrant and exciting with stunning architecture to view, unique attractions to visit, and fun things to do. Guided tours are the best way to enjoy these activities and places and learn about the history behind them. We have listed our favorite tours in Chicago that you must include in your itinerary.
Top 10 unique tours in Chicago including Chicago Ghost Tours
1) Chicago Crime Tours and Experiences
Chicago was rife with crime in the 1920s during the prohibition era with gangsters like Al Capone, Bugs Moran, and Tony Accardo ruling the city. The Chicago Crime Tours and Experiences take you on a guided but chilling tour through the past of the city's underworld.
Starting in a luxury bus surrounded by yellow crime tape, the tour explores several iconic locations that played significant parts in Chicago's crime history, such as Cook County Criminal Courthouse, the Biograph Theater, and the Holy Name Cathedral. There's also an evening variant of these called the Chicago ghost tours, which welcomes all ages and also makes more, stops across the city!
- Website
- Price: $39.95 for the Day tour and $45 for the Night Crimes Tour
2) The Gangsters and Ghosts Tour
The Gangsters and Ghosts Tour is hands down one of the best Chicago ghost tours in the city and indeed comes highly rated by both natives of Chicago and tourists to the Windy City.
With four tours held every day at 11 AM, 1 PM, 4 PM, and 8 PM, the Chicago gangsters and ghosts tour takes you on a guided experience through "the Loop," known as the central vice district of the turbulent 1920s.
The best part is that the Gangsters and Ghosts Tour isn't a theatrical tour. Everything you hear is an actual historical fact, making this haunted history tour an excellent opportunity to learn about Chicago's past.
- Website
- Price: $27 Adult, Senior Citizen $25, Youth $17, and Free for Children
3) Chicago Hauntings Ghost Tours
Sure, gangsters are scary, but what's even more scary is them sticking around as ghosts! The Chicago Hauntings Ghost Tours is a 3-hour tour by a bus filled with ghost stories, exploring some of the most supernaturally active spots in the city, sure to raise your hackles.
An award-winning Chicago ghost tour operated by paranormal researcher Ursula Bielski and her staff, the Chicago Hauntings Ghost Tours, has been personally responsible for introducing thousands of tourists to the spookier, scarier side of Chicago.
Psst: If you subscribe to their website, you even get a code for 10% off.
- Website
- Price: $49 Adults, $39 Children, Senior Citizens, and Military Servicemen
4) Chicago Architecture River Cruise
The Chicago Architecture River Cruise is a lighthearted, fun experience on a luxury cruise ship going down the Chicago River.
You'll see sights like Navy Pier, the John Hancock Building, the Old Post Office Building, and of course, the Sears building! Taking only approximately an hour and a half, the tour also explores all three branches of the beautiful Chicago River.
The tour is conducted almost every day from two starting spots: Michigan Avenue and Navy Pier, and gives you an excellent vantage point for exploring Chicago.
- Website
- Price: $35 to $48 Adults, $18 to $27 Children, and Children 2 and under free
5) Lake Michigan Sightseeing Cruise
If you're in Chicago and want to see the beauty it offers, look no further than the Lake Michigan Sightseeing Cruise, which tours along the picturesque Chicago lakefront.
Climb onto the luxury cruise ship for a guided forty-minute tour along most of the city's iconic waterfront landmarks, and if you're feeling hungry, bring lunch or even grab a drink from the onboard bar.
Here's a tip: we recommend bringing lunch that you can enjoy during the tour.
- Website
- Price: $27.25 Adults and $11.21 for Children
6) Speakeasy, explore hidden bars in Chicago
Exploring a city's food scene doesn't always mean the priciest restaurants. Sometimes it's the little cafes and the unique establishments like speakeasies that are the places to go.
The 'Speakeasy, explore hidden bars in Chicago' pub crawl is conducted by an experienced guide named Gus, who starts the tour at regular intervals in a month at his favorite stop in the West Loop. From there, he takes the tour group on a 3-hour tour of the city's best and most underrated speakeasies and cafes.
It's the ideal tour for people who want to experience the city's cuisine scene. Note, though, that this tour doesn't include food and drink. If you're going to eat, you'll have to pay!
- Website
- Price: $13 per person
7) Chicago Favorites Ultimate Food & Walking Tour
If you're a foodie, don't worry: we're not entirely done with the Chicago food tours yet!
Next on the list is the Chicago Favorites Ultimate Food & Walking Tour, known as the one must-visit tour for anybody who wants a serious taste (and a second helping!) of Chicago's cuisine.
The walking tour isn't just for people who like to eat, though. It easily covers a distance of 1.5 miles, which means you'll be walking off the delicious deep-dish pizza and Chicago hot dogs you eat right there, not to mention the chocolate.
- Website
- Price: $71.96 Adults, $67.84 Youths, and $11.30 for Children
8) Big Bus Chicago Night Tour
The Big Bus Chicago Night tour might sound a very touristy attraction, but this bus tour has been operating for years and is recommended by hundreds of tourists as one of the best sightseeing tours of Chicago you'll get!
The comfortable double-decker bus starts its loop at the famous Navy Pier, taking approximately 75 minutes to Michigan Avenue down the Magnificent Mile. It goes through the Museum Campus and loops around several of the most prominent architectural Gems dotting the Chicago Loop's skyline.
Getting a taste of the violent past of the white city, but if we're honest, almost nothing beats looking at the city's skyline from the upper deck of a bus!
- Website
- Price- $29.81 Adults, $19.53 for Youths, and it's free for children!
9) Chicago Beer Expedition
There are few things more relaxing than a cold beer, and if that beer's coming handmade from an authentic Chicago microbrewery, that's even better! The Chicago Beer Expedition, one of the most well-known Chicago brewery tours, explores several of the city's most famous microbreweries located in and around Fulton Market.
The tour begins at the first stop, where the entire group introduces themselves. You'll be treated to some delicious homemade Guacamole Tortilla chips and two handcrafted beers of your choice.
After that, the tour group walks to the different breweries one by one, where you can choose to try out all the famous handcrafted beers Chicago has to offer. Relax and enjoy the experience with Ronaldo, the host, who has hosted more than 200 people on the Chicago Beer Expedition!
- Website
- Price- From $39.08 per person
10) Underground Donut Tour: Chicago's First Donut Tour
Chicago might be called the Windy City, but we guarantee the sweets you'll find on the Underground Donut Tour will ward off the chill!
Touted as Chicago's first donut tour, this tour takes you to some of Chicago's most famous donut sellers, giving you a rare chance to sample every type of donut the city has to offer. Besides, let's be honest: where else are you going to find an utterly donut-themed tour but Chicago?
- Website
- Price: $30.84 for Adults, and $2.05 for Children under 11
That was our countdown of the best Chicago ghost tours and experiential tours in Chi-town! Want a Chicago itinerary planned around these tours and other attractions in the city? Hire one of Voyayge's travel designers who can create a customized itinerary based on your likes, preferences, and budget.