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Which Chicago Architecture Tours Are Best?

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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 options.



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. 

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. 

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). 

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


Save between 20%-45% with the Go Card.

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. 

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. 

Most passengers report that their tour guide was very knowledgeable, but used terms that were easy for everyone to understand. 

Read the reviews here.

Tour Information


Tour Length: 90 minutes with several departures each day. 10 am, 12 pm, 2 pm, 4 pm and 6 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.


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 and Viator (read the reviews).

Tour Information


  • $39 for Adults
  • $18 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.

History buffs, locals, and first-time visitors will love hearing how the Second City rose from the ashes to the major city that it is today from volunteer docents demonstrating enthusiastic knowledge and love for their city.

Many visitors recommend taking the Twilight Tour. For a few extra dollars, you will get to see the buildings lit up.

CAF also offers a special tour just for photographers, with three stops and assistance from volunteers to help you best capture the architectural achievements.

Duration: 90 minutes


  • Daytime Cruises $46
  • Twilight Cruise $51

Things to Consider:

  • Tour Departure Times vary; check the calendar here.
  • CAF requires ALL passengers to have a ticket; this includes infants and children.
  • Missed tours may not be subject to refunds or exchanges on tickets.
    • Tours take place rain or shine, but there are climate-controlled, covered areas of the boat’s lower level.
    • Full bar and restrooms available on the boat.
    • Boarding begins 15 minutes prior to departure time, and seating is general admission.

Location: GPS: 112 E. Wacker Drive (map)

Conveniently located along Wacker Drive, look for the blue awning at the southeast corner of Michigan Avenue Bridge.

There are stairs leading down to the water; travelers with limited mobility should use the ramp East of Wabash Avenue to descend to the river level.



While Seadog is most well known in the city for their thrill rides (see below), they also offer an architecture tour that combines lake views with your river cruise for an inclusive look at Chicago’s skyline innovation and design.  


Experienced Seadog patrons encourage you to arrive early with a pre-purchased e-ticket so that you are first in line to sit in the front half of the boat.

Remember to bring sunscreen, and always take the complimentary water offered!

Duration: 75+ minutes



Depart from South Navy Pier, 600 E Grand Ave (map).  Look for the red & white ticket booth just across from the Ferris Wheel.



While Kayak Chicago offers many tour options, their guided architecture tour is by far their most popular.

Never kayaked before? No problem; a paddling lesson is included.

Ride single or tandem on the Chicago River while getting closer to the water than any cruise ship can get you.

Duration: 3 hours




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

We offer a wide variety of walking tours in Chicago that you can experience Chicago's wonderful architecture.



Our guided tours are free to sign up to and operate on a pay-what-you-want basis.  

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 out our public calendar to see our current schedule.

Chicago Architecture Tour

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.


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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 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.

This tour is also popular during the spring and summer months, and that’s definitely the best time of year to experience the Riverwalk.

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!

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, but 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.

Get more information.



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. 


  • $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. 

Click here to learn more about Big Bus's tours and prices.  


Chicago Trolley & Upper Decker Company Tour

Much like the Big Bus Tour, this company also focuses its 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.

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.


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.

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.



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.

About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: October 12th, 2021
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