All Chicago Tours & Excursions in 2026 - page 21

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Prohibition Chicago: Myth vs. Reality Walking Tour

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always accurate. On this tour, you’ll hear how the culture in turn-of-the-century Chicago helped bring about the 18th Amendment through stories of notorious vice districts along the Chicago River and the South Loop. We'll talk about the rise of Al Capone during the infamous “Beer Wars,” culminating in the St. Valentine’s Day Massacre. Along the way, we’ll talk about how the city played a role in the popular and artistic growth of jazz, and how Chicago during the Roaring Twenties has been depicted on screen, in blockbusters such as "The Untouchables" and "Chicago." Please be advised that this tour contains stories of murder and sex work. Although children are welcome on this tour, parents should use their discretion in determining whether it is suitable for those under 15.

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Prohibition Chicago: Myth vs. Reality Walking Tour

2 hoursFree Cancellation

from $35

Bird Tours across Chicago

2 to 5 hoursFree Cancellation

5.0

(1)

from $60

Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer

Book your private arrival transfer from Chicago Midway Airport (MDW) to Chicago. Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer. Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination. • We track your flight. • Our driver greets you with a name plate. • We provide door-to-door service. • There are no hidden charges. • We use clean cars and professional drivers.

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Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer

35 minutesFree Cancellation

5.0

from $74

Price varies by group size

Architectural and Historical Private Tour in Downtown Chicago

To me, one can appreciate a given building, or piece of public sculpture, far better when a tour guide explains the historical and cultural context. What was important in that era, and what was the architecture of that era thus trying express? I do know a lot about this. Thus, you will gain this information about each point of interest. I have taken other tours here, and I just do not hear a word from that point of view. This tour will be like an open history book to an America that no longer exists: Roman and Greek architectural styles, as well as French and British-influenced styles. Of course, you will see the latest in office building architectural styles from around the world, for those of you who just love the modern era as well.

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Architectural and Historical Private Tour in Downtown Chicago

2 hours 20 minutes to 2 hours 30 minutesFree Cancellation

from $199

Per group

Chicago Photo Capture Your Adventure Walking Tour

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn fascinating stories about the city’s history and culture. At each stop, professional photos will be taken of you or your group, allowing you to take home original digital images that capture your adventure in the Windy City. - Visit five picturesque locations for memorable photos - Enjoy breathtaking skyline views throughout the tour - Receive original digital photos after the tour to keep the memories alive - Perfect for couples, families, or anyone wanting to explore Chicago through photography

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Chicago Photo Capture Your Adventure Walking Tour

2 hours 30 minutesFree Cancellation

from $49

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!

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Chicago-Milwaukee Small Group Tour

6 to 7 hoursFree Cancellation

3.0

from $485

Price varies by group size

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Top Attractions in Chicago

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What are people saying about Chicago

Chicago Architecture River Cruise

Heather_G, Jul 2026

Amazing Architecture Boat Tour

Such an amazing experience! We got great seats and truly all seats were great! What made the experience exceptional was our tour guide Joel! Hecwas so knowledgeable on everything Chicago! He certainly made the architecture tour one we will never forget!

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Chicago Favorites Ultimate Food and Walking Tour

Steve_C, Jul 2026

Great way to eat yourself around the city

Great range of foods. Good local knowledge and Molly was really enthusiastic about her home town, this showed throughout the tour. My wife had become vegetarian a few months before the 2 swapped choices were good and sorted with no fuss. We both left feeling full and knowing a lot more about Chicago

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Chicago By Night River and Lake Cruise

Lisa_G, Jul 2026

Very informative and beautiful

Taking the sunset architectural cruise near the Riverwalk was easily one of the highlights of our trip. Seeing the city's iconic skyline transition from the golden hour glow into the beautifully lit evening cityscape is an absolute must-do. The vessel was comfortable, the atmosphere was relaxed, and the tour provided fascinating insights into the history and design behind Chicago's world-famous buildings. If you want a peaceful, breathtaking, and informative way to experience the city from the water, this is it! Highly recommended.

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Chicago Sightseeing River and Lake Cruise

Victoria_G, Jul 2026

Best of both worlds

The best of both cruising worlds - Chicago river and the lake cruise in one! Hear about the architecture on the banks of Chicago River then go through the engineering marvel of Great Lock and end up on Lake Michigan, where the views of skyline 🏙️ are unmatched! Totally recommend

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Chicago Architecture Center River Cruise aboard First Lady

Monica_Z, Jul 2026

Chicago First Lady river cruise

The First Lady architecture cruise was fantastic! It is a great tour to do when first arriving in Chicago to get a nice layout of the city and the river. We learned a lot from the docent onboard and he gave us a lot of places to visit on foot afterwards. Highly recommend!

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Chicago River 45-Minute Architecture Tour from Magnificent Mile

Natalie_M, Jul 2026

Must do in Chicago

I’ve been to Chicago half a dozen times but have never done a river tour. I wish I would have done this sooner! Beautiful way to see the Chicago city skyline and learn interesting facts about the city. Our tour guide was exceptional and gave a lot of local recommendations. We did this tour with our young children and 45 minutes was the perfect time to keep them entertained. Would love to do the 90 minute tour next time we visit.

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Lake Michigan Sunset Cruise in Chicago

William_M, Jul 2026

We Loved It!

Wonderful experience! Gabby was a great tour guide who provided a lot of history and fun facts about Chicago. She is incredibly knowledgeable. The views were amazing, and the captain provided fantastic opportunities for photos, too! I would highly recommend this sunset cruise to anyone visiting downtown Chicago.

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Chicago Crime and Mob Bus Tour

Henry_C, Jul 2026

The host was fantastic...

The host was fantastic and his delivery was spot on. He kept it lighthearted and funny while still making it informative and interesting. I thought this was going to be a gangster tour with a focus on Al Capone, but they presented generations of crime stories, from the Chicago’s origins to the Crack dealing McDonalds employees. I was young when the Tylenol scare occurred and to go past the Walgreens where it happened was also interesting. The only negative feedback I can give is the bus broke down outside of Harry Cary’s and we had to figure out how to get back to the neighborhood we started in. Obviously this was a one off and I would not judge to tour by an unforeseen. Great tour and worth the price of admission.

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Chicago Lake and River Architecture Tour

Ioana_C, Jul 2026

Best tour of Chicago river and lake.

Best combination of lake and river tours. The Chicago skyline is wonderful to see it in its entire length and beauty from Lake Michigan. The tour guide was very knowledgeable and had a wonderful story to tell at “every corner”. Toilets were clean and there was no problem finding where to sit. We did not buy anything from the bar but everything looked clean and nice. Total duration of the tour is one and a half hours spent approximately half-half between the lake and the river part. Fun fact: lake is a couple of feet higher than the river and you can see that when crossing over during the tour. Chicago river flow direction was altered in the early 1900 to flow away from the lake and keep chicagos source of clean water intact.

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Lake Michigan Skyline Cruise in Chicago

Anisha_S, Jun 2026

Relaxing Ride

The skyline tour was exactly what I needed after a day of eating and walking about. I was able to book the tour an hour before, which worked for my itinerary and it was affordable. I liked that it is a double decker boat and got to experience the tour from top deck. The day was beautiful and perfect for a tour. The boat was clean, looked presentable, offered cocktails and small snacks(for purchase) and staff were friendly. The tour offered ok views. I was able to capture pictures of the Chicago skyline. My fav part of the ride was how relaxing it was. I would do it again and be sure to nap the next time lol.

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things_to_do

Chicago makes such a striking impression that you're best off discovering it from a few different vantage points. Luckily, Chicago tours offer multiple ways to see the city in style. Visit the observation decks in the Windy City's record-breaking skyscrapers for panoramic views; then, hop on a boat along the Chicago River. From there, zoom into a more local scale: Head out after dark to learn about the city's gangster history; explore its characterful neighborhoods on local-led walking tours—and don't forget to eat Chicago classics, from deep-dish pizza to Italian beef sandwiches, on a tasting tour.

People Also Ask

What are the best tours in Chicago?

How much do Chicago tours cost?

The cost of Chicago tours runs the gamut from roughly US$20–30 per person for a 45-minute architecture cruise to US$850 and up (depending on group size) for a private tour of the city. Most of the top-rated tours are under US$60 per person. No matter what you have on your agenda, there’s sure to be a tour that suits your budget.

On the lower end of the price range, you can book tours such as the Chicago Black History Highlights Walking Tour from US$5 per person. This hour-long group walking tour gives you a thorough introduction to Chicago’s Black history and culture and takes you to key African American landmarks in the city. Pricier options include VIP tours such as Chicago Private Boat Rental—Explore Chicago's Skyline & Waters, from US$2,275 per group (up to 12). This charter boat service provides the captain and crew, and you choose the itinerary—ideal for parties and celebrations or family vacations.

What do you see on Chicago tours?

There are dozens of subjects you can explore and sights you can see on Chicago tours, so what you see depends on which tour you choose. The city’s famous skyline gets the spotlight on architecture boat tours, and several walking tours highlight locations tied to Chicago’s history of organized crime. You can also see Chicago landmarks like the Cloud Gate sculpture (“The Bean”) in Millennium Park and the much-loved Field Museum of Natural History.

Consider an all-day tour to visit as many attractions and landmarks as possible. For example, the Chicago in a Day: Food, History, and Architecture Walking Tour takes you to many must-visit attractions and areas, including the Chicago Riverwalk, Millennium Park, Chicago Theatre, City Hall, Wrigley Building, Tribune Tower, and more.

How many days in Chicago is enough?

What is the best month to visit Chicago?

The best months to be in Chicago are spring shoulder seasons (specifically April–May) and fall (September–October). During these months, the weather isn’t as hot and humid as it can get in the summer, but it’s still pleasant enough for plenty of outdoor exploring. The summer calendar is packed with fun festivals and events, so summer can also be a great time to visit if you don’t mind the heat (or the crowds).

What are the best attractions in Chicago?

What are the best day trips from Chicago?

What are the best affordable things to do in Chicago?

What are the best outdoor activities in Chicago?

There are tons of Chicago activities to enjoy in the fresh air. Here are some of the top outdoor tours to book right now:

View all of Viator’s top outdoor activities in Chicago.

What are the best museums and exhibitions in Chicago?

What are the best activities for couples in Chicago?

Couples will find plenty of romantic tours in Chicago. Here are some of the top activities to book now, according to previous travelers:

View all of Viator’s top romantic tours in Chicago.

What are the best activities for families in Chicago?

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All Chicago Tours & Excursions in 2026 - page 21

400+ results

Top Attractions in Chicago

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Art Institute of Chicago

What are people saying about Chicago

People Also Ask