The Best Chicago Architecture Tours Reviewed

This post compares and reviews the many options for Chicago architecture tours with review analysis to help you choose which one is best for you, including our pay-what-you-like architecture tours, which can save you a lot of money. Expect to pay about $40 per ticket for boat tours. Bus tours are similarly priced at between $30-$40 each. 




If you thought the River Walk was impressive, imagine passing by historic skyscrapers as you float down the Chicago River. With so many wonderful buildings located near the water, it’s actually quite easy to experience an entire boat tour focused specifically on architecture.  

Be sure to also read our post comparing all Chicago boat tours.  

Shoreline Sightseeing Chicago Architecture Tour

Experience the story of Chicago’s most important architects as you pass their completed works on both sides of the river. Enjoy the skyscrapers and other unique structures that seem perfectly carved into the windy city.

Shoreline Sightseeing hires professional tour guides to offer an exceptional insight into Chi-town’s creation. This company is also well known for providing a laid-back excursion and a family-friendly atmosphere. Avoid paying full price by using the Chicago Go Card to save money on this boat tour!

TIP: Before paying full price, do note that this cruise is included for free in Chicago Go Card, a tourist attraction discount pass as well as part of Big Bus’s Triple Play package.  

Be sure to also read our post comparing the different tourist discount passes available in Chicago.



Shoreline Sightseeing Reviews

Shoreline Sightseeing has an overall 4 ½ out of 5 stars rating on TripAdvisor and Get Your Guide (see some of the reviews). Despite the fact that they welcome families, most of the reviews for their architecture tour come from couples.

That being said, almost every review for this service is positive. High-level contributors refer to it as both informative and humorous, suggesting that their tour guide provided them with a unique perspective on Chicago’s architecture.

The few negative comments seem to indicate that not every guest will appreciate the brand of humor employed by their tour guides, but most people appreciate the experience offered by this company.

Tickets and Tour Information


Tour Length: 75 minutes

Availability: This tour runs several times daily from April – November. Check the tour calendar for more information.

Chicago Line Cruises

On this boat tour, an award-winning docent will introduce you to more than 50 different skyscrapers and historic locations in Chicago. If your goal is to learn a lot about the architectural history of this city, you’ll struggle to find a service any better than what Chicago Line Cruises offers to their customers.

Prices are comparable to most of the other architecture cruises in Chi-town and ratings indicate that their tours are quite informative. Complimentary refreshments and snacks are provided on every cruise, including Starbucks coffee and cookies.




Reviews for this cruise line are very good, and most guests really enjoyed their architectural tour. Families and couples were the most likely customers to provide a positive review, indicating that this is a great option for most group sizes.

Most passengers report that their tour guide was very knowledgeable, but used terms that were easy for everyone to understand. It looks like a majority of impressed reviewers agreed that this is a wonderful experience for just about anybody.  Read the reviews here.

Tour Information


Tour Length: 90 minutes with several departures each day. 10 am, 12 pm, 2 pm, and 4 pm

Availability: Spring-Fall

Wendella Sightseeing Boats

This company provides Chicago’s Original Architecture Tour. Aboard their climate-controlled boats, you won’t have to worry about rain or wind getting in the way of your trip. Float down all three branches of the Chicago River as a professionally trained tour guide introduces you to this city’s wonderful architectural history.

Similar to other services, you will find a full-service bar with snacks and candy on the first floor. Wendella also offers a variety of very deep discounts for students, military, veterans and Chicago First Responders.


With over 80 years of history in Chicago, it shouldn’t come as too big of a surprise that Wendella Sightseeing enjoys a 4 ½ star rating on TripAdvisor. An overwhelming majority of reviews for their architecture tour are positive, and negative comments don’t seem to indicate any serious issues.

Thanks to their welcoming atmosphere, this tour is most frequently enjoyed by families, friends, and couples. Most customers agree that this trip is very informative and fun, while others simply enjoy it for the views.

Tour Information


  • $35.50 for Adults
  • $32 for Seniors
  • $16.50 for Children
  • Children 2 and under free

Tour Length: 75 minutes

Availability: Spring-Fall   

Purchase Tickets Here


Chicago Architecture Foundation River Cruise

If you’re looking for a well-informed tour, you can’t get much closer to the source than the Chicago Architecture Foundation.  In partnership with Chicago’s First Lady Cruises, they offer a 90-minute guided trip down the Chicago River, providing detailed explanations of the construction and history of over 50 significant buildings.

Whether you’re a history buff, a Chicagoan who wants to learn more about their city, or a first time visitor, this excursion through the Second City is sure to please a variety of audiences. In addition to their standard historical cruise, you can also take a night tour to see the same architectural wonders lit up after the sun goes down.



Review of Chicago Architecture Foundation Cruise

Almost every review of this service is positive, and the Chicago Architecture Foundation has an overall 5-star rating on TripAdvisor. Once again, this service is particularly popular among smaller groups of people, but CAF welcomes any and all guests.

It may be a tad more expensive than some of the other options on this list, but most reviewers agree that this architectural boat tour is worth the price.

Several guests were very impressed with their well-informed tour guides, but negative comments were quick to call them boring. This experience may not be perfect for all audiences, but it will more than likely be exceedingly informative.

Tickets and Tour Information


  • $44 – Daytime Architecture Cruise
  • $46 – Twilight Architecture Cruise:

Tour Length: 90 minutes

Availability: Like most boat tours and cruises in Chicago, CAF only offers this trip during the warmer months of the year. Check their calendar for more information.


Seadog River and Lake Architectural Tour

It may surprise some tourists to discover that a company which usually provides thrill rides also offers an architecture tour in Chicago. A lot of travelers come to the windy city to see its many architectural wonders, so it only makes sense to give them what they want.

If you’re looking for a more exciting educational experience on the Chicago River, this may be your best bet. While other cruises pride themselves on taking it easy, Seadog takes their tours up a notch and makes learning a lot more fun for guests of all ages.



This tour company has earned a 4 ½ star rating on TripAdvisor, and their architecture tour is very highly rated. Unlike some of the other tours on our list, you’ll find that families represent the largest audience for this cruise. An overwhelming majority of these reviewers were very pleased with their experience.

Many of the customers who left negative feedback felt that the trip was obnoxious, indicating that they might have been better off with a more quiet and informative boat tour.

That being said, the fun and exciting atmosphere provided by Seadog Cruises may be exactly what some audiences need to bring the history of Chicago to life.

Tour Information


  • $38.95 for Adults
  • $23.95 for Children
  • Get 10-15% off these prices with Trusted Tours.

Tour Length: 75+ Minutes.

Availability: As with most boat tours and cruises in Chicago, Seadog only provides service during the warmer months. Check their tour calendar for additional information.


Kayak Chicago Architecture Tour

If you’re looking for a more quiet and personal trip through Chicago’s incredible architectural history, you might want to consider this Kayak tour. After all, groups are usually going to be a lot smaller when you’re working with kayaks, and you’ll probably have a much easier time hearing your tour guide.

Don’t worry if you’ve never done this kind of activity before because a paddling lesson is included with every kayak trip. Whether you’re looking for a fun adventure for your family or you just want to discover Chi-town’s past from an interesting perspective, this service is sure to please.

Reviews of Kayak Chicago

Kayak Chicago currently enjoys an overall 4 ½ star rating on TripAdvisor. Most reviews for their architecture tour are positive, and the experience seems to be popular with almost every audience.

The few negative comments suggest that this excursion can get a little hairy when it is overbooked. Other than those complaints, most guests agreed that the views were fantastic and their tour guides were very informative. High-level contributors recommend bringing a towel, a change of clothes and some sunblock.

Tour Information


Tour Length: 3 hours

Availability: This kayak tour is offered every day @10 am, and they occasionally offer two architecture tours per day.

TIP: Although they offer free paddle lessons, you may want to avoid this option if you aren’t in good shape. You will be paddling for three hours, and this can be very challenging for many guests. Keep your own health and enjoyment in mind before purchasing tickets.


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Whether you want to save some money or you’d prefer to get some exercise on your trip, you might want to consider a walking tour of Chicago’s architecture. Stroll by some of the most notable buildings in the city and learn all about the history of their construction. There are both free and paid walking tours in Chi-town, and most of them are very highly rated.

Free Tours By Foot

It can be pretty expensive to visit the windy city, so it’s always nice when you can partake in a few activities that aren’t very costly. Thankfully, we offer a wide variety of walking tours in Chicago that you can experience Chicago’s wonderful architecture for free!

Our guided tours are pay-what-you-want, which makes it much easier to save some money.  We offer several tours that are either focused on or cover architecture. Each tour lasts about two hours and will require between 1 – 1 ½ miles of walking. Check our tour calendar for more information on availability.  

Check out our public calendar to see our current schedule.



Chicago Architecture Tour

Have you ever wondered how the skyscraper was created? If you want to learn more about how these tall buildings raced to the sky, this tour is an absolute must. Visit Chicago’s commercial core downtown and discover the innovation that went into creating the buildings in this area.

Find out more about the role that modernism played in the architecture of this city with a free tour which includes stops at The Sears Tower, The Federal Plaza, Grant Park and several other popular locations.

This walking tour has yet to receive any negative ratings on TripAdvisor. Almost everyone who went on this trip to downtown Chicago enjoyed themselves. 

This tour runs in Winter as a shorter 1.5 hour tour that pops in and out of lobbies to warm up on occasion. Make sure to dress for the weather as we still go outside.

Some topics we will cover on the Chicago Architecture Tour

  • Sears/Willis Tower
  • The Rookery
  • The Board of Trade building
  • Federal Plaza
  • The Monadnock
  • Grant Park
  • Buckingham Fountain

Tour information

Reservations: REQUIRED. Click here to reserve. Groups of 9 or more must contact us before booking. Groups of 6-9 must follow our group policy regarding prepayment for groups.

Where: 305 W. Jackson Bvd. — Meet on the Southwest corner of Franklin and Jackson-which is directly south of Willis Tower at the top of the stairs. 

*Our 1.5hour Winter Architecture Tour meets directly in front of the Marriott Hotel at 151 W. Adams*

Duration: Tour lasts approx. 2 hours. Total walking is just over one mile (1.6km).

When:  View our Calendar. Tours are on U.S. Central Standard Time.

Cost: This tour is free to take, and you get to decide what, if anything, the tour was worth when it’s done. A name-your-own-price tour is a tour for anyone’s budget.

Chicago Riverwalk and History Tour

This tour may not focus exclusively on architecture, but it’s hard to avoid that subject of conversation when touring any part of the windy city. After all, there are many buildings that line the waterfront in Chicago, and they all have a story to tell.

Walk along the river and find out how this city was built to complement the waterways with aesthetically pleasing views and an impressive use of space. Learn all about the architects who designed and constructed locations such as The Chicago Theater, The Wrigley Building, and The Chicago Tribune Building.

This tour usually runs in the evening, but we also offer it during the day.



Much like the Chicago Architecture Tour, the Chicago Riverwalk and History Tour have very high ratings on TripAdvisor. Once again, couples and individual travelers represent a large chunk of these reviews, but we welcome guests in groups of up to 10 people.

This tour is also popular during the spring and summer months, and that’s definitely the best time of year to experience the Riverwalk. High-level contributors suggest that the history you’ll learn about the city and its architecture are worth the trip. Get more information.

North Loop and Millennium Park Tour

When most people think of Chicago, images from various films and television shows fill their heads. Whether it’s the L train, Millennium Park or Daley Plaza, chances are you’ve seen this side of the windy city a bit more frequently than some of the places you’ll visit on our other tours.

Discover how the architecture and development of these locations influenced the overall construction of this city when you take a trip into the past with one of our excellent tour guides!

As you might expect, most of the reviews for this walking tour are very positive. We actually have yet to see a negative comment about our services. Once again, a majority of reviews come from couples and individual guests, but many visitors also bring their friends along.

Groups of up to 6 people are welcome, which could also make it perfect for small families. High-level contributors have nothing but positive things to say about our guides, indicating that they learned a lot while on the North Loop and Millennium Park tour. Get more information.

Magnificent Mile Tour

When it comes to shopping in Chicago, few areas are as notable as the Magnificent Mile. Filled to the brim with high-end stores, this district is not only a hotspot for travelers with deep pockets, it’s also a great place to see how business shaped the skyline of this city.

Find out what has drawn visitors to this stretch of Michigan Avenue for several generations. Join one of our tour guides for a trip past notable buildings such as The Tribune Tower, The John Hancock Building, and The Wrigley Building.

This particular tour is most popular among couples, and when you consider that it’s a trip around one of the most notable shopping districts in the world, it’s not too difficult to understand why. If you want to learn about the architecture behind the economic landscape of the windy city, dozens of guests recommend the Magnificent Mile Tour.  Get more information.


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One of the best ways to see Chicago is to take a bus tour. There are several services that will drive you around the most architecturally significant areas of the city. As you travel around Chi-town by bus, a tour guide will point out historically important buildings and tell you the story of their construction.

These architecture tours may be better for anyone visiting during the winter because they won’t require you to be outside for very long, if at all.  Due to the fact that great and interesting architecture is everywhere, just about every bus tour in the city is at least partially an architecture tour.  

If you’re going on a trip with your family, it may be a better idea to consider one of these general excursions over an experience devoted to learning about how this city was built.  Below are some of the more notable.  

Be sure to read our post which compares the best Chicago bus tours.


Chicago Architecture Foundation Bus Tour

In addition to their boat tour, CAF also provides an extensive architecture bus tour. Clocking in at over 3 hours in length, you can rest assured that you will learn a lot about Chicago while on this adventure. Over the course of this excursion, you’ll cover more than 30 miles of architectural history in the windy city. If you’re looking for a more educational experience, this is probably your best bet. Discover how the skyscraper was born and what has happened since it’s arrival in The Second City.

Almost all of the ratings for this bus tour are excellent. Although there are a few negative comments, they don’t indicate any serious problems with the service. A majority of positive reviews were provided between September and November, suggesting that this might be a good option for anyone visiting the windy city during the fall. As with most of their services, they welcome guests of all kinds, but this trip seems to be more popular among couples and customers who bring along their friends.


  • $45 for General Public
  • $37 CAF members

Tour Length: 3 ½ hours

Availability: This tour is typically available at least once a week. Check their tour calendar for more information.


Big Bus Tours 

Although this isn’t exclusively devoted to the history of architecture in Chicago, you can actually learn a lot about how this city was built on the hop-on, hop-off bus tour from Big Bus. In addition to the information you’ll receive from their tour guides, you will also have the opportunity to jump off at many architecturally significant locations along the way. Discover landmarks such as The Chicago Theater, The John Hancock Center, Sheraton Towers, Millennium Park and Grant Park.  Except for winter, they also offer a double-decker night tour that is a great way to see Chicago’s illuminated architecture.  If you decide to use Big Bus, you could supplement their service with our more in-depth, pay-what-you-wish architecture walking tours.

Despite the fact that they don’t focus solely on architectural information, there are actually a lot of positive reviews indicating that this hop-on-hop-off bus tour could be a great way to experience the windy city. Some customers suggest that this company should provide more material on the history of the architecture in Chicago, but others seem to appreciate the ability to hop off and discover many of these locations on their own.

Click here to learn more about Big Bus’s tours and prices.  Bid Bus 1 day tickets are included at no additional charge with the purchase of the Chicago Go Card.


Chicago Trolley & Upper Decker Company Tour

Much like the Big Bus Tour, this company also focuses their efforts primarily on providing a Hop-on, hop-off service. They don’t have any tours specifically devoted to architecture, but you’ll have an opportunity to jump off at several different landmarks and explore the windy city for yourself. Enjoy stops at Skydeck Chicago, The John Hancock Center, Millennium Park, The Magnificent Mile and Michigan Avenue Bridge. Learn the history from hands-on experience at each specific location on this bus tour.

During the summer, they also have a tour package which will take you to Wrigley Field, Skydeck Chicago, The Chicago History Museum and the Lincoln Park Zoo. This might be a great option if you want to learn about the architecture behind one of the oldest baseball stadiums in the United States.

Several reviews for this service suggest that the tour provides a lot of information about architecture and the history of Chicago. That being said, some customers have taken issue with the lack of focus on this subject, indicating that this trip is more about having fun than learning about historical facts. Depending on your approach to discovering the architectural history of Chi-town, you may want to consider a more in-depth bus tour. A majority of positive ratings came from families, so this may be a better option for kids.

Availability: Much like the other hop-on-hop-off bus tours, Chicago Trolley & Upper Deck Company provides services on almost every day of the year.

Click here to learn more about their tours and prices.


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Anyone planning to explore more than just the architecture of Chicago might want to consider obtaining a tourist pass. Several tour companies provide combo passes which include access to a variety of different attractions. These discounts can make it easy for you to discover the engineering history of the windy city and move on to other activities when you are ready.  

Passes come in 3 varieties: all-inclusive, a la carte and build-your-own passes. Depending on how you craft your itineraries, these cards will save you anywhere from 20% – 50% off of retail prices and are certainly worth the consideration.  

You can read our full comparison of all available passes on our Chicago tourist discount pass post.  Below, we listed some highlights related to the architecture buff.

Go Chicago Card

This company offers a variety of passes to fit the needs of almost any traveler. Whether you’re going to be visiting for a few days or a week, you’ll find plenty of options available on the Go Chicago card.

Many of the attractions and activities offered through this tourist pass are focused on architecture, with one example being admittance to the Chicago Architecture Foundation. While you’re there, you can partake in one of the many tours they offer or learn about the history of the windy city.

Here are some of the other notable architecture tours and attractions they offer which are focused on the architectural history of Chi-town:

  • Architecture River Cruise
  • Skydeck Chicago
  • 360 Chicago
  • Big Bus Hop-on, Hop-off Tour
  • Frank Lloyd Wright Home and Studio Tour
  • The Chicago Theater Marquee Tour
  • Admittance to The Robie House
  • Panoramic and Scenic North Side Tour
  • Historic Chicago South Shore Tour

Learn more about their products.

Chicago CityPass

Although the story of Chicago’s architecture might not be the focus of this tourist pass, you can still learn a lot with the help of this combo ticket. Two of the activities included are a perfect complement to any architecture tour, allowing you to experience the city from a unique perspective.

The Chicago CityPass booklet gives you access to two observation decks which allow you get a better look at the design of these buildings. If you intend to visit even one observation deck in the windy city, you may want to consider getting this pass.

Attractions Included

  • Skydeck Chicago
  • Shedd Aquarium
  • The Field Museum
  • 360 Chicago OR Museum of Science and Industry
  • Adler Planetarium OR Art Institute of Chicago


TIPS: In order to take advantage of everything offered through the Chicago CityPass, you will want to allow yourself at least 3-4 days for exploration. If you’re only going to be in the city for a few days, you may want to consider a different option.  

Combine this pass with some of our self-guided or pay-what-you-wish guided walking tours if you want to save money and see as much of Chicago as possible.

Other Tourist Passes

For more information on alternative tourist passes in Chicago, check our comparison post discussing the best combo deals available. Not only will you learn more about the options we’ve already discussed, but you’ll also discover many other opportunities to save money on various activities.


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Self Guided Chicago Architecture Tours

If you’d rather take matters into your own hands, you can always try out one of our many self-guided walking tours in Chicago. Alternatively, you can combine these self-guided adventures with some of the other activities we have already mentioned above in order to make the best use of your time without spending too much money.

No schedule is necessary for these excursions, and you are free to explore at your own leisure. Many of our self-guided walking tours focus at least some attention on architectural history, making them a perfect complement to any vacation focused on learning about Chicago’s architecture. We offer the following self-guided touring options:

  • Navy Pier
  • Millennium Park
  • Wrigleyville
  • Wicker Park
  • Downtown Theater District

In addition to these choices, you can also discover a lot of unique architecture by visiting locations such as Chinatown and Little Italy on one of our self-guided food tours. To learn more about all of these wonderful activities, visit our list of self-guided Chicago walking tours.


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There are a lot of walking tours in Chicago, so if you’re looking for an opportunity to get off your feet, a Segway might be the perfect option. Although the Segway tours in Chicago don’t focus exclusively on architecture, you can still experience a lot of the architectural history of the Second City on one of these fun and exciting trips. Free Tours By Foot has partnered with City Segway Tours in order to offer a 10% discount on all of their tickets.

City Segway Tours sport an overall 5-star rating on TripAdvisor. An overwhelming majority of reviews for this service are positive, and some guests suggest that their tour guides provide a lot of information about the architecture in Chicago. Others found their architectural discussion lacking but still had a pretty good time on their trip. Most positive reviews came during the summer, and it would seem that this is a great time to travel around Chi-town on a Segway.

To learn more about this option, please visit our post on Chicago Segway Tours.