15 Best Tours in Chicago (by a Local)

Written by Rachel Thompson
Updated on
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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.

I’m a Chicago local and have been on many tours with friends and family visiting. To get you started here’s my list of the best tours in Chicago.

1. Chicago Skydeck + “The Ledge” Experience Ticket

Chicago SkydeckSource: Salvador Maniquiz / shutterstock
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.

2. Chicago River Architecture Cruise

Chicago River Architecture CruiseSource: getyourguide.com
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. This is actually one of the tours I personally like most for first-time visitors. You can also check out my guide on the best boat tours in Chicago.

3. Wicker Park Walking Food Tour

Wicker Park Food TourSource: getyourguide.com
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.

4. 90-Minute Mob and Crime Bus Tour

Mob And Crime Bus TourSource: getyourguide.com
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

Palmer House HotelSource: gary yim / shutterstock
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. I highly recommend taking a walking tour on the first day of your visit, it offers plenty of tips on what to do the coming days as well.

6. Chicago Secret Food Tour

Chicago: Secret Food TourSource: www.getyourguide.com
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 savor 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

Loop Interior Architecture Walking TourSource: getyourguide.com
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.

Related readingBest Things to Do in Downtown Chicago

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

Chicago Hop-on Hop-offSource: getyourguide.com
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.

I recommend it as a great way to get around the city during your entire visit (there’s 24, 48 and 72 hour option).

9. Gourmet Brunch, Lunch, or Dinner River Cruise

Gourmet Brunch, Lunch, or Dinner River CruiseSource: www.getyourguide.com
Gourmet Brunch, Lunch, or Dinner River Cruise

Delight your taste buds with a scrumptious meal prepared by talented chefs, offering a variety of brunch, lunch, or dinner options. Knowledgeable guides provide captivating commentary on the city’s history and architectural wonders, showcasing landmarks like Willis Tower and Navy Pier.

This unique blend of exquisite cuisine, breathtaking scenery, and informative narration promises an unforgettable journey through Chicago’s heart.

Read next15 Best Day Trips from Chicago

10. Chicago’s Modern Skyscrapers Guided Walking Tour

Chicago SkyscrapersSource: Rudy Balasko / shutterstock
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. Private Helicopter Flight

Private Helicopter FlightSource: www.getyourguide.com
Private Helicopter Flight

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. Might be an obvious tip but I recommend this experience during a clear day.

12. Navy Pier Centennial Wheel

Navy Pier, ChicagoSource: Felix Mizioznikov / shutterstock
Navy Pier

The Chicago Navy Pier Centennial Wheel offers an exciting experience at one of the city’s most iconic landmarks. With this tour, visitors can enjoy stunning views of Chicago’s skyline and Lake Michigan from the impressive Centennial Wheel. The tour provides various ticket options, allowing guests to customize their experience.

Whether opting for a standard ride, a fast pass, or a private gondola, I highly recommend it to take in breathtaking panoramic view of the city.

Related15 Best Hotels in Chicago

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

Bobby's Bike Hike ChicagoSource: getyourguide.com
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.

14. Chicago South Side Tour with Optional River Cruise

Chicago South SideSource: viator.com
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

Haunted Bar TourSource: getyourguide.com
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.

15 Best Tours in Chicago (by a Local):

  • Chicago Skydeck + “The Ledge” Experience Ticket
  • Chicago River Architecture Cruise
  • Wicker Park Walking Food Tour
  • 90-Minute Mob and Crime Bus Tour
  • Treasures of Chicago’s Golden Age: 90-Minute Walking Tour
  • Chicago Secret Food Tour
  • Loop Interior Architecture: 2-Hour Walking Tour
  • Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe
  • Gourmet Brunch, Lunch, or Dinner River Cruise
  • Chicago’s Modern Skyscrapers Guided Walking Tour
  • Private Helicopter Flight
  • Navy Pier Centennial Wheel
  • Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour
  • Chicago South Side Tour with Optional River Cruise
  • Chicago Haunted Bar Tour