Top 15 Local Tours in Chicago You Can’t Miss

Chicago, often referred to as the Windy City, ranks as the third-largest city in the United States, showcasing a myriad of attractions for every visitor. The metropolitan area offers diverse experiences, including culinary delights, craft beverages, architectural marvels, and rich historical insights.

Local tours provide insightful opportunities for visitors to immerse themselves in the essence of Chicago. With a knowledgeable guide, the city’s unique culture and history come alive, allowing you to truly understand what drives the spirit of the Windy City.

As a resident of Chicago who has participated in numerous tours with friends and family, I present a curated selection of the best tours available in the city.

1. Chicago Skydeck + “The Ledge” Experience Ticket

The Willis Tower stands as the tallest skyscraper in Chicago, and your ticket enables access to its summit.

As you ascend, several exhibits provide insights into Chicago’s heritage and the profound cultural ties that bind the city. Once you reach the pinnacle, courageous visitors can venture onto ‘the Ledge,’ a series of four glass balconies offering expansive views of the city and the streets below.

Additionally, a compelling presentation detailing the construction of the Willis Tower is included with your ticket.

2. Chicago River Architecture Cruise

This river cruise offers a tranquil way to explore Chicago while discovering the city’s architectural heritage and the stories behind its landmarks.

The 75-minute journey encompasses over 40 monuments and notable bridges, complemented by live commentary from an on-board guide. For first-time visitors, this experience is particularly enjoyable.

3. Wicker Park Walking Food Tour

Chicago’s culinary scene thrives in neighborhoods like Wicker Park, known for its diverse food offerings. This three-hour tour, led by a knowledgeable local, invites you to savor authentic Chicago fare from five unique eateries.

As a delightful dinner tour, it provides ample food to satisfy your appetite, making it advisable to arrive hungry.

4. 90-Minute Mob and Crime Bus Tour

This intriguing bus tour unveils the history of organized crime in Chicago, covering notorious figures like Al Capone and John Dillinger.

During this 90-minute exploration, you will visit various sites impacted by criminal activity and gain insight into the lives of the city’s most infamous mobsters.

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

The late 19th century marked a period of significant growth for Chicago, and this tour guides you through key architectural landmarks from that transformative era.

Your adept local guide will share insights on the historical factors that fueled Chicago’s expansion while highlighting pivotal events that continue to shape the city.

Focusing on the individuals who contributed to the city’s development, this walking tour provides a personal connection and valuable recommendations for your extended stay.

6. Chicago Secret Food Tour

Although Chicago boasts numerous renowned dining establishments, this tour highlights hidden culinary gems that are often overlooked by visitors.

Embark on a three-hour walking tour through the Loop District, where you will explore six distinctive locations while learning about the significant impact of Italian immigrants on the city’s gastronomy.

The pace allows for a leisurely appreciation of the flavors on offer, with some beverage pairings included. As you savor the dishes, you’ll also gain insights into the local art and architecture, creating an enriching adventure on your first evening in Chicago.

7. Loop Interior Architecture: 2-Hour Walking Tour

This tour immerses you in the iconic interiors of Chicago’s famous buildings, examining how spectacular architecture extends beyond exteriors.

Led by an expert local guide, you will explore building entrances and corridors while uncovering the historical significance encapsulated within their walls. An exploration of the underground Pedway System reveals how it shaped the city’s infrastructure and transformed the daily lives of its residents over the decades.

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

Hop-on-hop-off bus tours serve as an excellent introduction to a new city, allowing you to become familiar with key landmarks and attractions. This tour covers all major sights, permitting you to explore at your own pace.

Audio guides enhance the experience by providing informative commentary in multiple languages. Tickets can be customized for one or two days, with an option for a night bus included. Complimentary WiFi is available, along with a bag of Garrett’s Popcorn for your enjoyment during the tour.

9. Gourmet Brunch, Lunch, or Dinner River Cruise

Indulge in exquisite meals crafted by skilled chefs, with options for brunch, lunch, or dinner available. Knowledgeable guides will share engaging narratives about the city’s history and architectural highlights, featuring iconic sights such as Willis Tower and Navy Pier.

This exceptional fusion of delectable cuisine, stunning scenery, and informative storytelling promises to deliver an unforgettable experience through the heart of Chicago.

10. Chicago’s Modern Skyscrapers Guided Walking Tour

Featuring some of the tallest buildings in Chicago, this walking tour allows you to appreciate the most iconic skyscrapers in the city.

Your local guide will delve into the history of these structures, discussing the architectural innovations that have made a significant impact on the city’s skyline.

You will gain insights into the modernist movement that has shaped Chicago’s architectural identity and continues to inform contemporary designs.

11. Private Helicopter Flight

If you’re seeking a remarkable evening tour of the city, this helicopter excursion is an excellent choice for those willing to invest in a memorable experience.

Your pilot, a licensed and experienced local, will provide high-quality commentary as you soar above the skyline, viewing everything from skyscrapers to the expansive Lake Michigan.

All safety equipment is included, and guests receive a briefing before departure. It is advisable to schedule this experience on a clear day for optimal visibility.

12. Navy Pier Centennial Wheel

The Navy Pier Centennial Wheel provides an exhilarating experience at one of the city’s most renowned landmarks. Visitors can relish spectacular views of Chicago’s skyline and Lake Michigan from the impressive structure. Various ticket options allow customization based on preferences.

Whether opting for a standard ride, a fast pass, or a private gondola, this experience offers breathtaking panoramic vistas of the city.

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

This Lakefront Neighborhoods Tour, showcasing some of Chicago’s wealthiest areas, combines a leisurely biking experience with exploration of the local culture.

Visitors can appreciate local mansions and the Lincoln Park Zoo at a relaxed pace. As the tour finishes near the Lakeside area, you’ll find excellent opportunities for photography. This family-friendly tour caters to participants of all ages.

14. Chicago South Side Tour with Optional River Cruise

For those fascinated by the city’s heritage, the South Side presents a compelling area to explore.

On this tour, an experienced local guide will share insights about the city’s founding and highlight significant landmarks that reflect Chicago’s intricate and vibrant history.

The tour includes a visit to Jackson Park for recreation, finishing at the Art Institute, which holds the world’s largest collection of Impressionist art.

15. Chicago Haunted Bar Tour

Every major city is steeped in ghostly tales, and Chicago is no different. This tour delves into the city’s intriguing past, sharing eerie stories along the way.

It guides you to four distinct bars, offering an opportunity to appreciate the ambiance while enjoying local beverages. Spanning approximately two and a half hours, this tour provides a unique evening out in Chicago.