15 Best Tours in Chicago

The Windy City is the third largest city in the United States and comes with a variety of delights for any visitor. From food and craft beer to architecture and history, the Midwestern metropolis is packed with exciting experiences.

There are a variety of great tours run by locals across the city that help you dive deep into the things that matter most to Chicagoans.

The unique history and culture of the city is best discovered with a local guide, and these tours will help you to dive deeper into what makes the city tick.

Here are the 15 best tours in Chicago.

1. Chicago Skydeck + “The Ledge” Experience Ticket

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Chicago Skydeck

The Willis Tower is the tallest Skyscraper in Chicago and this ticket allows you to go to the very top.

There are a bunch of exhibits on the way, to teach you about Chicago’s history and the deep cultural roots that connect the city. Once at the top, brave visitors can step into ‘the Ledge,’ a series of four glass balconies that give you views across Chicago as well as over the street below.

A theatrical presentation is also included in the ticket, which discusses the construction of the Willis Tower.

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2. Chicago River Architecture Cruise

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Chicago River Architecture Cruise

For a more relaxing tour experience, this river cruise takes you down the Chicago River whilst also discovering the architecture of the city and the history behind some of the most iconic buildings.

The 75-minute-long tour passes more than 40 different monuments, as well as a variety of the city’s most well-known bridges.

The commentary is provided by a live guide on board the ship, and there is a bar available for you to purchase refreshments and drinks.

3. Wicker Park Walking Food Tour

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Wicker Park Food Tour

Like many cities across the United States, Chicago is well known for its growing food culture and Wicker Park is a hub for the culinary scene in the city. This three-hour tour is conducted by a local with extensive knowledge of the best food to try in the city.

You will sample typical Chicagoan food from five different restaurants in the area, all offering their own little slice of the city. This is a great dinnertime tour that will provide you with more than enough food to make a full meal, so come with a full appetite.

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4. 90-Minute Mob and Crime Bus Tour

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Mob And Crime Bus Tour

Discover the dark underbelly of Chicago from the safety of a tour bus with this tour, which tackles the history of mobsters and criminals in the city.

You will learn about Al Capone, John Dillinger and many other famous criminals from the city in this tour which lasts around 90 minutes.

You will be shown the different sites that have been influenced by crime in the city, and be able to follow in the footsteps of the most notorious mobsters. You can also delve deeper into the history of the subject at the small mobster museum located in the city.

5. Treasures of Chicago’s Golden Age: 90-Minute Walking Tour

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Palmer House Hotel

The city experienced a major boom in the late 19th century, which extended right through to the early years of the following century.

This tour takes you around all of the architectural highlights from the era when the city was in major expansion and people were flocking from across the United States to the Windy City. Your skilled local guide will discuss the different factors that influenced Chicago’s expansion, as well as highlight the important historical events that still shape the city to this day.

This tour focuses on the people that built Chicago, giving it a nice personal touch.

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6. Chicago Secret Food Tour

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Chicago: Secret Food Tour

Chicago is full of famous restaurants and bars, however this tour aims to take you to the best restaurants that are not well-known by visitors.

You will visit six different spots around the Loop District of Chicago, and learn about the important influence Italian immigrants had on the city. The walking tour takes around three hours to complete, and is paced so you can truly savour all of the dishes you are sampling.

Some drinks are also included. The tour also discusses the local art and architecture in the area, making it a great tour for your first evening in the city.

7. Loop Interior Architecture: 2-Hour Walking Tour

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Loop Interior Architecture Walking Tour

This tour takes you inside the most famous buildings to talk about how the magnificent architecture has been taken indoors.

You will get an extensive tour of the entrances and corridors of these buildings from a knowledgeable local guide, who will discuss the history found within their walls and the lives of the architects who designed them.

You will also be able to check out the underground Pedway System, which has shaped how the rest of the city was designed and changed the lives of locals for decades.

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8. Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe

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Chicago Hop-on Hop-off

Hop-on-hop-off bus tours are a great way to become acquainted with a new city and gather your bearings. This tour takes you to all of the main sights in the city for you to explore at your own pace.

Audio guides are included to give you more information, and these are available in multiple languages. You can customise your ticket to last either one or two days, and to also include a night bus option.

Free WiFi is available on all of the buses, and all guests are given a free bag of Garrett’s Popcorn to snack on whilst enjoying the tour.

9. 3-Hour 3-Course Buffet Dinner Cruise

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Buffet Dinner Cruise

Enjoy a freshly prepared dinner buffet whilst also taking in the spectacular urban landscape of Chicago with this three-hour-long cruise.

This evening cruise will allow you to take in the sparkling nightlife of Chicago from the comfort of the ship, and a full three-course meal is provided. Dancing and music are also included on the cruise, helping to create a very fulfilling nighttime experience for guests.

Non-alcoholic beverages are included, and alcoholic beverages can be purchased on board.

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10. Chicago’s Modern Skyscrapers Guided Walking Tour

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Chicago Skyscrapers

Chicago has some of the highest skyscrapers in the city. If one of your main aims for your trip is to check them out, then this walking tour can help you take in the most famous buildings in Chicago.

The local guide will help you understand the history behind all of the skyscrapers, as well as talk at length about the innovations made by architects in the city.

You will learn more about the modernist movement that shaped the city’s skyline and still influences new buildings to this day.

11. City Lights Helicopter Experience

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City Lights Helicopter Experience

For the ultimate nighttime tour of the city, this helicopter experience is a fantastic option if you are looking to splurge.

The pilot is fully licensed and experienced, and comes from the local area so is able to provide high-quality commentary about all of the sights you can see from the sky.

From skyscrapers, to the wild waves of Lake Michigan, you can truly see it all from this helicopter experience. All safety equipment is provided and customers are given a short briefing before take-off.

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12. Signature Food Tour at Navy Pier

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Navy Pier

The Navy Pier area is another great place to sample the best of Chicago cuisine. A local expert is provided to help you get the best culinary experiences the city has to offer.

All of the main cuisines Chicago is known for can be found on Navy Pier, and you will also be able to enjoy the fun atmosphere of the pier as well as great views over the urban landscape.

This two-hour tour not only gives you additional context behind all of the food you are sampling, but it also means you can skip the long lines that many of the establishments have.

13. Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour

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Bobby’s Bike Hike Chicago

Featuring some of the wealthiest districts in Chicago, the Lakefront Neighborhoods Tour can provide a relaxed and fulfilling experience during your stay in Chicago.

This tour is done on bikes, helping you to enjoy a more active adventure as well as explore the neighbourhoods at an easy pace. You will be able to check out the local mansions, as well as the Lincoln Park Zoo.

The Lakeside area, where the tour ends, is also a good spot for photo opportunities. This tour accepts all ages, making it a good option for families.

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14. Chicago South Side Tour with Optional River Cruise

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Chicago South Side

For visitors more interested in the history of the city, the South Side region is definitely worth a visit.

In this tour, a local guide will talk to you about the founding of the city, and the important landmarks in the South Side region that display the complex and vibrant history of Chicago.

You will also be taken to Jackson Park to enjoy some recreational activities, and to the Art Institute to see the world’s largest collection of Impressionist Art.

This two-hour tour finishes up at the University of Chicago, where you can enjoy the ornate English architecture.

15. Chicago Haunted Bar Tour

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Haunted Bar Tour

Most major American cities have their ghost stories, and Chicago is no exception. Learn all about the macabre past of Chicago and hear captivating ghost stories along the way.

This tour takes you to four different bars across the city, where you can spend some time soaking up the atmosphere and enjoying a local beverage. The tour lasts around two and a half hours, and is great if you are looking for a unique night out in the city.

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