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Locally Guided Chicago Tours

Locally Guided Chicago Tours

7 tours in Chicago, from US$49 per person, lasting 2.5 to 4 hours, with at most 10 guests per tour. Prices checked Nov 1, 2026. Rated 4.6/5 from 50 verified reviews across 5 tours. Change-of-Plans Guarantee: free cancellation up to 24h before.

See Chicago’s skyline, history, and stories beyond the Bean with small group Chicago tours.

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  • 4.6/5 (50 reviews)
  • Change-of-Plans Guarantee: free cancellation up to 24h before
  • 7 tours

Tours in Chicago, United States

4.650 verified guest reviews across 5 Chicago tours

Boat Tours(6)Walking Tours(4)Small-Group Tours(6)

Visit Adler Planetarium Skylin with Best of Chicago Tour.jpg

Best of Chicago Tour

4.6(41 reviews)
Tickets includedSkip-the-line
  • Skip-the-line entry to Skydeck Chicago and step onto The Ledge on the 103rd floor of Willis Tower
  • Relax on Shoreline Architecture Cruise and see over 40 iconic Chicago landmarks from the river
  • Capture stunning views of Chicago’s skyline and Lake Michigan from Adler Planetarium Pier viewpoint
  • Visit to Cloud Gate (The Chicago Bean) – One of the city's most iconic public art pieces
From$129
Check Availability
Buckingham Fountain at Dusk
Chicago, United States

Scenic Chicago Night Tour

  • 3.5 Hours Duration
  • Next: Dec 31
  • Max 10 Guests Per Group
From$169USD
Best of Chicago History & Architecture Walking Tour with Boat Cruise.jpg
Chicago, United States

Best of Chicago History & Architecture Walking Tour with Boat Cruise

  • 3.5 Hours Duration
  • Next: Dec 31
  • Max 10 Guests Per Group
From$104USD
Best of Chicago History & Architecture Walking Tour.jpg
Chicago, United States

Best of Chicago History & Architecture Walking Tour

  • 2.5 Hours Duration
  • Next: Dec 31
  • Max 10 Guests Per Group
From$49USD
Best of Chicago Walking Tour.jpg
Chicago, United States

Best of Chicago Walking Tour

  • 4 Hours Duration
  • Next: Jul 1
  • Max 10 Guests Per Group
From$189USD
Visit Ledge Chicago Night Tour.jpg
Chicago, United States

Best of Chicago Exclusive Private Tour

  • 4 Hours Duration
  • Next: Dec 31
  • Max 10 Guests Per Group
From$519USD
Chicago, United States

Chicago Small Group Walking Tour with Skydeck and Boat Cruise

  • 4 Hours Duration
  • Next: Dec 31
  • Max 10 Guests Per Group
From$159USD

Compare our Chicago tours

Compare our Chicago tours
TourDurationGroup sizeFrom priceIncludesPickupRatingNext dateBook
Best of Chicago Tour4 hoursUS$1294.6/5 (41)Check availability
Scenic Chicago Night Tour3.5 hoursUS$169Check availability
Best of Chicago History & Architecture Walking Tour with Boat Cruise3.5 hoursUS$104Check availability
Best of Chicago History & Architecture Walking Tour2.5 hoursUS$49Check availability
Best of Chicago Walking Tour4 hoursUS$189Check availability
Best of Chicago Exclusive Private Tour4 hoursUS$519Check availability
Chicago Small Group Walking Tour with Skydeck and Boat Cruise4 hoursUS$159Check availability

Pickup, departures and good to know

Pickup

Your guide will pick you up and drop off at your downtown Chicago hotel. (Best of Chicago Tour)

McCormick Tribune Plaza, 1 N Michigan Ave, Chicago, IL 60602, USA (Best of Chicago History & Architecture Walking Tour with Boat Cruise)

Willis Tower - 222 South Riverside Plaza, Chicago, IL, USA (Best of Chicago Walking Tour)

Meeting point

McCormick Tribune Plaza — McCormick Tribune Plaza, 55 N Michigan Ave, Chicago, IL 60602, USA

222 South Riverside Plaza — 222 S Riverside Plaza, Chicago, IL 60606, USA

Next departures

Best of Chicago Tour: Thu, Dec 31 at 9:00 AM CST

Best of Chicago Exclusive Private Tour: Thu, Dec 31 at 9:00 AM CST

Chicago Small Group Walking Tour with Skydeck and Boat Cruise: Thu, Dec 31 at 9:00 AM CST

Languages

English

Group size

Up to 10 guests

Cancellation

Change-of-Plans Guarantee: free cancellation up to 24h before

How long is a Chicago tour?

Chicago tours run from 2.5 to 4 hours. Best of Chicago Tour takes 4 hours.

Compare all Chicago tours

How much does a Chicago tour cost?

Chicago tours cost US$49 to US$189 per adult.

Prices are per adult and were checked on November 1, 2026.

Compare all Chicago tours

Which Chicago tour is best?

Best of Chicago Tour has the most reviews of our Chicago tours (41 reviews, rated 4.6/5) and takes 4 hours; see the comparison table.

Compare all Chicago tours

What is the refund or cancellation policy for day tours?

Full refunds will be issued to guests that provide notice of cancellation via e-mail or telephone at least 24 hours prior to departure time for all day tours. Cancellations made with less notice than the time frames listed above will be subject to a $50 per person cancellation fee.
See all Chicago tours

What is the best time to visit Chicago?

The best times to visit Chicago are April through May and September to October, this is when the temperatures are warm and the city comes alive with a variety of festivals.
See all Chicago tours

Tickets & Attractions in Chicago

Tilt Experience at the 360 Tower in Chicago

360 Chicago + TILT Experience

Chicago

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Buckingham Fountain Chicago

Chicago

Chicago Pedway.jpg

Chicago Pedway

Chicago

Chicago Riverwalk.jpg

Chicago Riverwalk

Chicago

Cloud Gate (Chicago Bean)

Cloud Gate (Chicago Bean)

Chicago

Crown Fountain.jpg

Crown Fountain

Chicago

Millennium Park.jpg

Millennium Park

Chicago

Navy Pier.jpg

Navy Pier

Chicago

Tours by Category in Chicago

Boat Tours in ChicagoWalking Tours in ChicagoSmall-Group Tours in Chicago

What Travelers Say About Chicago

Read our reviews on TripAdvisor

Book Direct with the Local Team

Rated 4.7/5 across Viator, TripAdvisor, Google & more.

  • Best-price guarantee when you book direct
  • Change-of-Plans Guarantee: free cancellation up to 24h before
  • Direct line to the team that runs your tour
  • Instant confirmation
+1-888-961-6584

Plan your Chicago trip

All travel guides

About Chicago

Chicago, a city that thrives on its rich history, modern architecture, and vibrant culture, offers visitors a variety of exciting experiences. If you're planning a Chicago trip, there’s no better way to explore the city than by hopping on one of the best Chicago tours. For a comprehensive experience, the Best of Chicago Tour takes you to some of the most iconic spots in the city, like the stunning Cloud Gate (Chicago Bean) and the world-famous Buckingham Fountain Chicago. These landmarks are just the beginning, with Chicago’s stunning architecture, world-class museums, and vibrant neighborhoods awaiting you.

For those who want to delve deeper into the city’s architectural wonders, the Best of Chicago History and Architecture Walking Tour with Boat Cruise combines a stroll through the city's architectural masterpieces with a relaxing boat ride. The Shoreline Architecture Cruise is another great option, offering a detailed view of Chicago’s architectural skyline from the water, showcasing the city’s towering skyscrapers and iconic buildings. If you’re looking for a more private experience, the Best of Chicago Exclusive Private Tour lets you explore Chicago at your own pace with a personalized itinerary that’s tailored to your interests.

If you're visiting during the evening, the Scenic Chicago Night Tour gives you the chance to see the city come alive with twinkling lights and stunning views of the skyline. This is a must-do for anyone wanting to experience the beauty of Chicago after dark. For those who enjoy a more intimate tour, the Best of Chicago Walking Tour takes you through Chicago’s historic streets and bustling districts, offering a local’s perspective on the city’s culture and history.

One of the best ways to see the city from a different angle is with boat rides in Chicago. The Shoreline Architecture Cruise is perfect for those who want to learn about Chicago’s architectural history while enjoying the beautiful view of Lake Michigan. Whether you're cruising past the skyscrapers or admiring the views from the Skydeck Chicago and The Ledge, Chicago’s boat tours are a memorable way to take in the scenery.

From the Cloud Gate to the Skydeck, every corner of Chicago offers something unique, making it a top destination for tourists. Don’t miss out on experiencing all the best this city has to offer, and book one of the many Chicago tours with See Sight Tours for a truly unforgettable adventure.

Traveler FAQs for Chicago

What is Chicago famous for?
Chicago, also known as the WIndy City is known for many things including Chicago-style hot dogs, its deep dish pizza, 1920s gangsters like Al Capone and its beautiful architecture such as the Sears Tower and the Chicago Bean.
What are the most popular things to do in Chicago?
There are many sites and attractions to visit in Chicago including; a relaxing shoreline architecture cruise, Buckingham Fountain, for those seeking adventure there is the Skydeck Chicago and The Ledge as well as the 360 Chicago plus TILT Experience and of course no trip to Chicago is complete without a visit to the Chicago Bean (Cloud Gate).
What airports are nearest to Chicago?
The nearest airport is 8.5 miles away, the Chicago Midway Airport (MDW).
When will my guide pick me up for my tour?
We will email or call you 1-3 days prior to your tour to confirm a specific pick up time. If you do not have access to phone or email, please be ready and waiting in the hotel lobby half an hour before your tour starts.
What top attractions are a must-see in Chicago?
Must-see attractions include the Cloud Gate (Chicago Bean), Skydeck Chicago and The Ledge, Buckingham Fountain Chicago, and the Shoreline Architecture Cruise. Each offers a unique glimpse into Chicago’s charm and culture.
What are the most popular tours in Chicago?
The Best of Chicago Tour, Scenic Chicago Night Tour, and Best of Chicago History and Architecture Walking Tour with Boat Cruise are among the most popular. They cover the city’s top landmarks and offer unforgettable experiences.
What are the best day trips and excursions from Chicago?
Day trips often include visits to nearby places like Oak Park for its Frank Lloyd Wright homes or the shores of Lake Michigan. Chicago also offers excursions to the historic town of Galena and the beautiful dunes at Indiana Dunes National Park.
Are Chicago tours available year-round?
Yes, the best Chicago tours are available throughout the year, offering different experiences depending on the season. From winter holiday tours to summer evening cruises, there's something for every time of year.
Do I need to book tours in advance?
It’s recommended to book tours in advance, especially during peak tourist seasons. Booking ahead ensures you get your preferred time and spot for popular tours.
What is the best time of year to visit Chicago for tours?
The best time to visit is in spring and fall when the weather is mild, and the city is not overcrowded. Summer also offers great weather for outdoor tours like the Scenic Chicago Night Tour.
Are there tours suitable for families with children?
Yes, there are family-friendly tours such as the Best of Chicago Tour, which provides a fun and educational experience for all ages. These tours feature iconic sights and engaging activities for kids.
Can I customize a private Chicago tour?
Yes, with the Best of Chicago Exclusive Private Tour, you can customize your itinerary to focus on the attractions that interest you most, ensuring a personalized and memorable experience.
How long do you need to see Chicago?
A weekend is typically enough to see Chicago’s major attractions, including the Skydeck Chicago and The Ledge, Cloud Gate, and a Shoreline Architecture Cruise.
Are food and drinks included in the tours?
Food and drinks are not typically included in most tours, but some, like specialized food tours, may offer tastings or snacks. Be sure to check the details when booking.
What is there to do in Chicago in the winter?
In winter, you can visit indoor attractions like the Art Institute of Chicago, take a Skydeck Chicago and The Ledge Experience, or enjoy a cozy Scenic Chicago Night Tour to see the city’s holiday lights.

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