Chicago’s urban skyline, sprawling parks, and winding river make it a city best explored with a thoughtful tour. Unlike many places that rely heavily on self-guided exploration, Chicago offers a range of guided experiences that reveal its architectural marvels, haunted history, and foodie hotspots. Whether you’re marveling at the legendary skyscrapers from a boat, biking along Lake Michigan, or uncovering ghost stories in Lincoln Park, each tour offers a unique perspective on the Windy City. With so many options—each with its own flavor—you’re sure to find a tour that fits your style and schedule. Planning ahead is key; Chicago’s busy summer months mean booking early can secure you a spot on the most popular tours.
Quick Overview
In this guide, we cover 16 of the best city tours in Chicago. From the iconic Chicago City Tour with Architecture River Cruise to specialized walks like Windy City Ghosts and private options such as Chicago Private City Tours, there’s a tour for every interest and budget. You’ll find detailed descriptions, practical tips, and insights into what makes each experience stand out.
1. Chicago City Tour with Architecture River Cruise Option
This combination tour is perfect for soaking up Chicago’s iconic skyline from land and water. Starting with a comfortable minibus ride, the tour covers Downtown and North Side neighborhoods, stopping at key sights like Millennium Park, the Buckingham Fountain, and the Museum Campus. The highlight is the optional architecture river cruise—a favorite among architecture lovers—that cruises along the Chicago River, showcasing the city’s famous skyscrapers such as the Wrigley Building and Tribune Tower. With small groups limited to just 10 people, the experience feels personal and engaging. Many guests appreciate hotel pick-up from most Downtown hotels, making logistics hassle-free. The reviews praise the knowledgeable guides and the flexibility of the tour.
Bottom Line: An excellent choice if you want a rundown of Chicago’s landmarks with insider commentary and a chance to see the city from a different perspective on the river.
2. Chicago: City Minibus Tour with Optional Architecture Cruise
For around $48, this minibus tour offers a flexible way to explore Chicago’s main sights and neighborhoods. It includes stops at famous landmarks like Buckingham Fountain and the Chicago River, plus three photo stops, including one with a view of the skyline. The tour is enhanced with an upgrade option for a 75-minute architecture cruise, which many find the best way to appreciate Chicago’s skyline and design. The guides are known for their friendly, knowledgeable commentary, making it a hit even on rainy days. Guests especially like the short, well-paced stops that maximize sightseeing without tiring everyone out.
Bottom Line: A solid choice for travelers wanting a land-and-water experience with the flexibility to skip or add the cruise.
3. Windy City Ghosts: Hauntings of Chicago Walking Tour
If you’re intrigued by Chicago’s spookier side, this after-dark walking tour explores haunted spots linked to gangsters, jazz musicians, and Civil War burial grounds. Starting in Lincoln Park, you’ll visit places like the haunted burial ground of Julia Porter and the former asylum at Alphawood Foundation Building. Your guide recounts macabre legends and ghost stories that bring Chicago’s darker history to life, or perhaps to restless spirits. The tour is small-group and lasts about an hour, making it intimate and lively. Reviewers love the storytelling skill and the atmosphere, with some upgrading for more stories and scares.
Bottom Line: Ideal for history buffs and night owls who enjoy spooky stories with a touch of history.
4. Chicago Explorer Pass: 25+ Things To Do – Includes Skydeck
If you prefer the flexibility of choosing your sights, this Explorer Pass is a smart move. Starting at $84, it includes access to over 25 top Chicago attractions, such as the Skydeck Chicago, Navy Pier, and the Museum of Science and Industry. You can pick 2 to 7 attractions, customizing your trip without the hassle of individual tickets. The pass is digital and easy to use, and many reviews highlight the savings and convenience. The Skydeck offers incredible panoramic views from the Willis Tower’s 103rd floor, making it a popular highlight.
Bottom Line: Perfect for travelers who want to see a variety of sights at their own pace and save money.
5. Chicago: Ultimate City Attractions Bike Tour
Bike tours are a fantastic way to cover more ground and enjoy Chicago’s lakefront and parks. This 3-hour guided ride takes you through Millennium and Grant Parks, Museum Campus, and Northerly Island, all while enjoying Chicago’s famous skyline and lakeside scenery. Riders praise the solid bikes, enthusiastic guide, and the opportunity to stop at modern sculptures and learn about the city’s architectural history. The tour is suited for active travelers, and the pace is manageable for most levels.
Bottom Line: Great for active visitors who want a mix of outdoor fun and cultural insights in a single trip.
6. Chicago: Ghosts & Hauntings of the Windy City Walking Tour
This second ghost-themed tour offers a slightly different route, focusing on mobster legends and serial killers in Northside Chicago. The walk explores Lincoln Park’s most haunted spots, including Oz Park and the former gangster hangouts. The 1-hour tour is brisk but engaging, with local guides sharing grisly stories and paranormal encounters. Many find this tour ideal for history and ghost story lovers who want a quick, spooky experience.
Bottom Line: A good pick if you prefer a shorter, urban ghost walk with a focus on Chicago’s criminal past.
7. Chicago Private Foodie Tour: Windy City Faves
This private food tour is perfect for culinary enthusiasts eager to taste Chicago’s famous deep-dish pizza, Italian beef, hot dogs, and more. Over four hours, you’ll visit top spots like Portillo’s and Al’s #1 Italian Beef, with plenty of food and stories about the city’s history. The private setting ensures a personalized experience, with your guide sharing local culture and food secrets. The cost reflects the personalized nature and quality, making it ideal for food lovers seeking an immersive experience.
Bottom Line: A must-do for foodies wanting an exclusive, comprehensive Chicago culinary adventure.
8. Chicago: ORD Airport Private Transfer to Chicago City|Hotels
For hassle-free arrivals and departures, this private transfer from O’Hare Airport is dependable. For $40 per person, you’ll enjoy a comfortable, air-conditioned ride with luggage assistance. Many reviews highlight the punctuality and friendly service. It’s a practical choice for travelers who want to skip the taxi lines and start their trip smoothly or end it comfortably without navigating Chicago’s busy streets.
Bottom Line: An efficient, stress-free option for getting to your hotel, especially after a long flight.
9. The Devil in the White City: A Haunting History Tour
Inspired by the book, this half-day bus tour explores Chicago’s 1900s’ notorious serial killer H.H. Holmes and the 1893 World’s Fair. Visiting sites like the Murder Castle and Jackson Park, the tour blends history and ghost stories in a compelling narrative. The guide shares entertaining insights into Chicago’s Victorian era, and the tour includes both on-foot stops and bus travel. Guests appreciate the informative commentary and the chance to see famous landmarks with a dark twist.
Bottom Line: Ideal for those interested in Chicago’s murderous past and the history of the 1893 World’s Fair.
10. Round Trip Private Transfer ORD Airport to Chicago City Oak Brook
This round-trip private transfer offers a comfortable and reliable way to get between O’Hare and your Chicago hotel or residence in Oak Brook. For $91.66 per person, you’ll enjoy flight-tracking and luggage assistance, with no waiting or detours. Many reviewers mention the timeliness and polite driver service, making it a smart choice after a long flight.
Bottom Line: Perfect for travelers prioritizing timing and comfort on arrival and departure day.
11. Chicago City Tours
Offering customized experiences for groups of up to 4, this personalized private tour allows you to tailor your sightseeing. Starting at $199, you can pick key landmarks like Millennium Park, the Wrigley Field, or the University of Chicago. The tour includes photo stops and flexible timing. Reviewers appreciate the seamless organization and the personal touch of having a guide focused entirely on your interests.
Bottom Line: Best suited for small groups seeking a flexible, private guide to see Chicago at their own pace.
12. Chicago 6-Hour City Tour by Sedan
This luxury private tour is designed for those with limited time but a desire to see the major sights. For just $960, two people can enjoy a full day of sightseeing in a private sedan, hitting Wrigley Field, Michigan Avenue, Millennium Park, and the Museum Campus. The guide can customize stops along the way, and many reviewers praise the friendly service and insightful commentary.
Bottom Line: Excellent for couples or small groups wanting a luxury, all-in-one Chicago overview.
13. Chicago Luxury Minibus City Tour and Architecture River Cruise
This combination tour blends a 90-minute minibus tour of downtown Chicago with a guided boat cruise. You’ll visit the Cloud Gate, explore the Museum Campus, and enjoy fine commentary from guides on both legs. The tour offers great photo opportunities and a thorough look at Chicago’s architecture and skyline. Many reviews mention the professional guides and well-organized schedule.
Bottom Line: Ideal for travelers who want a comprehensive, high-end experience blending land and water.
14. 4-Hour Chicago City Tour by SUV
This private SUV service is perfect for those with tight schedules. For $800, up to six people get a customized tour with flexible stops at sights like Navy Pier, Michigan Avenue, Millennium Park, and the Museum Campus. The private driver handles logistics, letting you focus on sightseeing. Reviewers like the timeliness and the personalized service.
Bottom Line: Best for groups needing a quick, flexible, and private tour.
15. Private City Tour 6-10ppl
For groups up to ten, this private vehicle tour offers a customizable 3-4 hour experience. Starting at $770, it includes stops at landmarks like Wrigley Field, Millennium Park, and the University of Chicago, with a professional guide. Guests love the personalized attention and the chance to not only see the sights but also learn about Chicago’s culture.
Bottom Line: Great for larger groups wanting an intimate, tailored Chicago sightseeing day.
16. Chicago, Cloud Gate, Grant Park Full-Day City Tour
This full-day coach tour covers all major highlights, including Millennium Park, Grant Park, and Michigan Avenue. You can customize your experience with add-ons like a river cruise or the 360 Chicago Observation Deck. It’s perfect for first-time visitors wanting a rundown. Many reviews mention the friendly guide and the well-paced itinerary.
Bottom Line: An all-in-one, flexible tour ideal for newcomers wanting a complete Chicago introduction.
How to Choose the Best Chicago City Tour
When deciding on a tour, consider your budget, interests, and schedule. If you’re after maximal flexibility and want to design your own day, the Explorer Pass or private tours may be best. For architecture enthusiasts, the river cruise or architecture-focused tours shine. If ghost stories and local legends appeal, the Haunted Chicago walks or Ghosts & Hauntings are perfect. Active travelers should look at bike tours, while those who value comfort might prefer private car services or multi-day passes.
Final thoughts
Chicago offers a diverse array of tours that showcase its spectacular architecture, lively neighborhoods, and intriguing history. Whether you want a detailed architecture cruise, a ghostly walk, or a private custom experience, there’s an option suited to your interests and schedule. For first-time visitors, the full-day city tour or 6-hour private sedan are excellent choices to get a broad overview. For those seeking fun with a bit of thrill, ghost tours deliver stories that stick with you long after dark.
Remember to book early, especially in peak months, to secure your spot on these popular experiences. With so many choices, you’re sure to find a Chicago tour that makes your visit memorable—just bring your curiosity and comfortable shoes.