Top Chicago Historical Tours - page 4

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time and pace that works best for you. Discover Gold Coast landmarks from historic piano bars to the original Playboy Mansion, and stop and start the tour whenever you like.

4.8

(99)

from $35

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

Likely to Sell Out

Haunted Ghosts & The Chicago Outfit Segway Tour

Take your architecture spotting off the streets and inside some of the most iconic buildings in Chicago with this unique Art Deco-themed tour. Get up close and personal with the glamorous style of the early 20th century as you delve beyond the downtown facades to explore glorious interior spaces from the 1920s and 1930s, with their ornate brass and marble details, mosaics, stained glass, and other treasures that most architecture tours miss.

4.7

(38)

from $75

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at your own pace and schedule -Professionally produced, narrated and musically edited immersive experience -Guided by technology. Put your phone in your pocket as the smart phone tour guided you with voice turn by turn. -Great deal -See and learn about Chicago's haunted spots, tragic events, fires, and the spirits that stayed behind. -Listen again after taking the tour. -The tour never expires, go or listen (after the on location tour) anytime. This haunted adventure is a smart phone guided on location tour. You go to the first stop, open the tour, enter your experience code and press play. From there you are guided turn by turn through Huntsville. The app knows your location and seamlessly guides you each step of the way.

4.9

(119)

from $35

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

1 hour to 1 hour 15 minutesFree Cancellation

4.8

(5)

from $10

Explore the Historic Old Post Office in Chicago

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old Post Office would be lost to time while the building sat vacant for almost two decades. But the 2.8 million square foot building, completed in 1934, recently went through a monumental renovation and now serves as a modern multi-use event and office space that meets today's need for large, light-filled workspaces. See how historic artifacts and building details have been creatively incorporated into the Old Post Office's design including the conversion of the roof to a 3.5-acre urban rooftop park. Old places can become new spaces when a developer with vision collaborates with an award-winning architectural team.

Explore the Historic Old Post Office in Chicago

Explore the Loop's famous architecture—and learn insider facts and stories that you wouldn't encounter if exploring alone—on this small-group walking tour. Led by your Chicago Architecture Center–certified guide, you'll discover some of the city's oldest skyscrapers, dating from the late 19th and early 20th centuries. Admire the Rookery building, see the Marquette building, and much more, all while soaking up the city's ineffable energy.

(25)

from $15

Chicago Walking Tour: Historic Skyscrapers

Dive into Chicago’s Magnificent Mile on an interactive scavenger hunt, perfect for families, friends, or team building! Guided by clues on your phone, you’ll solve puzzles, unlock local legends, and discover iconic sites like the Old Water Tower, Tribune Tower, and bustling Riverwalk—plus hidden gems along the way. Go at your own pace, compete for fun, and see the best of Chicago’s lively downtown in a whole new way. Teams of up to six welcome; no local knowledge required—just curiosity and comfy shoes.

4.8

(72)

from $35

Magnificent Mile Scavenger Hunt: Chicago Walking Tour and Game

Magnificent Mile Scavenger Hunt: Chicago Walking Tour and Game

from $25

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful characters, and insider tips to enhance your list of Things to do in Chicago. Your experience includes a FREE 2-hour bike or kayak rental—bike the Lakefront Trail or kayak on Lake Michigan for unforgettable skyline views. Bobby’s Bike Hike tours are nationally recognized by National Geographic, USA Today, and Condé Nast Traveler for excellence in storytelling and urban exploration. You’ll see the landmarks that define Chicago: Millennium Park, the Chicago Riverwalk, the Wrigley Building, the Chicago Theatre, and the famed Magnificent Mile. Covering 1.5 miles (2.25 km) of easy, flat terrain, this tour offers a complete and memorable introduction to the city.

Visit Cloud Gate on our Chicago Walking Tour—a Walking Tour of Chicago featuring Top Attractions, iconic art, and unforgettable Highlights at the city’s most photographed landmark.

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

Immerse yourself in the pizza culture of Chicago on this hearty lunch tour. Enjoy deep dish—and then go beyond it, with commentary from your food-loving guide and tastes of four different pizza varieties. Learn all about Chicago's history and culinary heritage as you go, and receive an introduction to the city's pizza scene that's more in depth than what other tours offer, with lunch included.

(6)

from $45

Chicago West Loop Pizza Crawl

3 hours

Enjoy an immersive way to discover Chicago's more recent architectural heritage with this small-group walking tour. Led by your architectural expert guide, you'll discover many of the Windy City's modern, postmodern, and other newer structures, including works by architects like Mies van der Rohe, Bertrand Goldberg, and beyond. As you go, your guide will point out the buildings many visitors overlook, and share stories from their history you wouldn't otherwise hear.

(9)

from $79

Chicago Walking Tour: Modern Architecture

Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.

4.9

(67)

from $35

Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

1 hour 30 minutes to 2 hoursFree Cancellation

There’s so much amazing architecture in Chicago but wandering around alone can leave you overwhelmed, and unsure of what you’re looking at. Check out some of Chicago's most important new buildings on an architecture walking tour. The tour is focused on the area around the Chicago Architecture Center (CAC), beside the Chicago River, so you don’t get overwhelmed exploring the whole city. Admission to the CAC’s galleries is also included.

(76)

from $70

Chicago Architecture Walking Tour: What's New

Chicago Architecture Walking Tour: What's New

Take a deep dive into Chicago's food scene on a small-group walking tour. Head for several of the city's most-notable eateries, including Billy Goat Tavern, known for its "cheezborger," Pizzeria Uno, birthplace of Chicago’s legendary deep-dish pies; and Al’s Beef, a favorite since 1938. Along the way, hear about the friendly rivalry with New York's pizza scene, Chicago's meatpacking roots, 1920s speakeasies, gangsters, and more.

(90)

from $35

Chicago Food and Culture Walking Tour

Sample three different styles of pizza all in one day: this Chicago tasting tour offers a delicious way to explore. In the evening, meet your guide at the first restaurant, and be sure to come hungry—you’ll sample everything from the city’s iconic deep-dish pizza to Neapolitan and artisan slices. In between, meet the pizza makers and learn more about the Windy City’s culinary history.

4.3

(19)

from $42

Friday Night Pizza Crawl - River North, Chicago

2 hours 30 minutes

This is not a bus tour, 90% of our tours are 11 people or less, as we specialize in small, personalized group tours. This gives us the space and time to take pictures and have great conversation! The personal, small tour approach allows travelers to have a personal tour experience of the city. With our small tour there are opportunities for questions and non-scripted conversations. A true experience. We have additional tours that accommodate large groups but this tour is geared towards sights and fluid conversations about the black starts of Chicago! The guide will take photos for you while educating you on the city and it's historical residents. On the Chicago Soul House tour, travelers tour the South Side of Chicago and can see the homes of the city's stars. The antidotes and stories are being told by someone who sang at the same lounges as Jennifer Hudson, played with Muhammad Ali as a child and traveled to Chicago during the Great Black Migration.

(3)

from $79

Home of the World's Heavyweight Champion, Muhammad Ali.

2 Hour Private Chicago Soul House Tour

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot and by L train, and see the city’s most iconic landmarks like The Rookery Building, Chicago Cultural Center, First Arts Building, and more 19th and early 20th-century masterpieces. Be ready to see the City by the Lake from a new perspective and get to know it even closer as you stroll down its streets and travel by train. Enjoy the small-group experience and don’t miss a thing as you travel Discover the downtown and historical building together with your local knowledgeable guide Marvel at architectural landmarks of the City by the Lake and get to know the stories behind them Combine a walking tour with a train to see more landmarks and iconic sights on one tour.

4.0

(5)

from $65

Chicago Architecture Tour - Skyscrapers, History and Photo Ops

2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover. Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket! Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules. Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids. Get Started: 7 Days of Premium Access available instantly for iPhone and Android.

from $89

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

7 daysFree Cancellation

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, followed by a step into the opulence of the Palmer House Hilton lobby. Admire the sleek lines of the Carbide and Carbon Building, a testament to Art Deco elegance, before appreciating the historic significance of the Reliance Building. Conclude your architectural odyssey with a visit to the exquisite Chicago Cultural Center, a masterpiece of design and culture. Throughout the tour, your knowledgeable guide illuminates Chicago's rich history and architectural evolution, weaving captivating stories that offer insight into the city's vibrant past and enduring legacy.

(2)

from $12

Chicago Highlights Private Walking Tour with a Guide

Chicago Highlights Private Walking Tour with a Guide

from $129

Original Chicago Prohibition Bus Tour

Free Cancellation

Discover the hidden gems of Lincoln Park on a private, open-air pedicab ride guided by a local storyteller. Relax as you explore lush gardens, the iconic lily pond, lakefront views, and landmark architecture— all without the effort of walking or the crowds of bus tours. Your route and pace are fully customizable, with plenty of photo stops and personal stories that bring Chicago’s past to life. Perfect for families, visitors with mobility needs, photography lovers, or anyone seeking a breezy, memorable Chicago adventure.

(3)

from $55

Enjoy a private pedicab tour through Lincoln Park with your friends, family or partner- every tour is customized to what your party wants to see and do!

Lincoln Park Secrets: Private Enchanted Pedicab History Tour

1 hour to 1 hour 10 minutesFree Cancellation

from $125

Chicago Riverwalk Self-Guided Walking Tour

1 to 2 hoursFree Cancellation

4.0

(8)

from $15

A Chicago hot dog loaded with bold, colorful toppings is one of the tastiest Things to do in Chicago. Our Chicago Food Tours feature this classic bite, making Food Tours in Chicago unforgettable.

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors with its most iconic landmarks. Savor Chicago Pizza, Hot Dogs, Italian Beef, Garrett’s Chicago Mix Popcorn, and the original Palmer House Brownie, or elevate your day with our VIP craft beer upgrade. This unforgettable Chicago in a Day Tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more, guided by true local experts. Enjoy a 5-hour journey through culture and cuisine, plus a FREE 2-hour bike or kayak rental to continue the adventure along Lake Michigan. Recently honored among the “Top 10 Food Tours in America” (USA Today) and “Top 20 Food Tours in the World” (TripAdvisor), this award-winning Culinary Tour is one of the top Things to do in Chicago. Don’t miss the most delicious, scenic Full Day Food Tour in Chicago—all in one extraordinary day.

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

5 hoursFree Cancellation

Chicago Art Heist: Millennium Park Puzzle Adventure

(2)

from $99

Special Offer

1 hour 35 minutesFree Cancellation

4.0

(10)

from

Chicago Walking Tour: Historic Treasures of Chicago

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Samuel_L, Aug 2026

A great way to spend a morning in Chicago

I will add to all of the positive reviews here and say that we had a wonderful experience with our docent. She brought to life the history of Chicago and the efforts made by volunteers and organizations to preserve these beautiful buildings. Highly recommended.

Private Art Institute of Chicago Skip-the-Line Guided Tour

MARK_P, Aug 2026

Excellent tour with Spiro

Excellent tour with our guide, Spiro. Our small group had all levels of interest and experience - from novice to seasoned, and Spiro expertly led us through the museum with emphasis on the Impressionists. He additionally took the time to address questions and other interests. Seeing the museum with a guide as fun and knowledgeable as Spiro elevated our experience. Highly recommend.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

KATHLEEN_M, Jul 2026

Awesome way to spend few hours!!

I live in the Chicagoland area. We just wanted to go to the city and do something different. This tour was awesome. Not too much walking, got to go in a lot of buildings with air-conditioning so the weather was not too much of an issue. We just loved it. Learned so much about buildings that we see every day but I’ve never actually gone into. Highly recommend it for locals as well as out-of-towners. Kate was an awesome guide if you can get her I’d recommend that as well.

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Ann_W, Jul 2026

Fun Evening Tour

Great tour. Guide had lots of fun stories to share, the walk was easy with frequent stops for questions by our group members. Group was small, which always makes tours better. All guides refer to Chicago’s first serial killer but I’ve yet to be led by one over the last 3 years who’s read Devil in The White City! Just surprises me. It’s a great book by a great writer, Erik Larson, that gives much information about the city’s World’s Fair and the murderous H. H. Holmes.

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Yolanda_M, Jun 2026

Great tour!

I have been on several segway tours over the years and feel like there are less opportunities to explore cities via segway. Fortunately, my husband and I were guided by Kevin in Chicago. After completing the waiver sheets, helmet fitting and training, we were off. We began our tour near Millennium Park and were able to ride through Grant Park and along the Michigan Lake coast. We were able to see some of Chicago’s highlights while having fun. Kevin was always willing to snap a picture of us too. I recommend it!

Chicago Architectural River Cruise

Marcia_H, May 2026

Architectural river boat cruise

The Chicago Riverboat Architecture tour is a must do if you travel to or live near Chicago. I have taken these tours in past years when I lived in the city, and I’m always impressed with and proud of Chicago’s international renowned reputation regarding historic building architecture as well as the recent and ongoing architectural achievements that make up Chicago’s downtown and skyline. The tour I booked via Viator was excellent because of the docent’s knowledge of Chicago’s building history and architectural significance. I highly recommend this tour!

Chicago's Original Gangster Tour by Bus

DulceMaria_D, May 2026

So gangsta! ⭐️⭐️⭐️⭐️⭐️

Honestly, this exceeded my expectations. I’m a Chicagoan and it felt like I experienced a visit to my own city. It was two hours of “wow” with orchestrated 1920’s music evolving into blues..it was amazing. I recommend and appreciate people like our guide who obviously value our city’s richest history. This was more than a gangsta historical tour, you learn a lot more about origins and impacts. I left being a little extra proud of our city. Thank you! 🎩💐

Paint your own street art at Studio WIP

Alana_M, Apr 2026

Great experience. Do it. Date night, birthdays, creative outlet, just go.

Camile was a great instructor and had such a good vibe. Learned some really helpful techniques from him ( creating text, drip, splatter and overlay/drop shadow) that were easy to incorporate into our work. We also had a minute to practice on the walls. They had canvases prepared and a ton of spray paint colors to share with the group. In addition to that there were a lot of stencils to choose from. I would only say that there needs to be better ventillation. But other than that, it was a great experience and we would definitely do it again!

Field Museum of Natural History Admission Tickets

Julie_C, Mar 2026

Too Much for 1 Day

There is so much to see and explore. Get rest before coming and go see the things you’re interested in first. There is so much to see and experience that it can’t be done in a single day. My kids have very different tastes and we split up. There was something of intense interest for both.

Vito's Vault Chicago Speakeasy Dinner Theatre

Stephen_L, Oct 2025

Join Vito and the Gang for a great night... Just don't forget the password😉

Absolutely brilliant evening! Vito and the team put on a fantastic night. A small, intimate speakeasy-style bar and restaurant with stunning 1920s-inspired décor. Dinner was delicious, and the service was excellent. The show was outstanding — a perfect mix of amazing singing, lively dancing, and plenty of laughs! Huge thanks to Vito and the team for such a wonderful experience that we both thoroughly enjoyed. Just don’t forget the password 😉 Stephen 🇬🇧