Things to do in Chicago, Illinois (IL): The Best Literary, Art & Music Tours

April 13, 2022 Russell Mellin

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago

1. 2-Hour History of Chicago Architecture and Art Segway Tour

300 E Monroe St, Chicago, IL 60601, USA Absolutely Chicago Segway Tours
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5.0 based on 15 reviews

See Chicago’s landmark architecture, outdoor sculptures and famous skyline by Segway! This family-friendly guided tour is both an exciting and educational way to explore Chicago. Plus, you'll save your feet from a day of walking and instead, quickly glide along the lakefront soaking in views of the spectacular skyline while seeing some of the tallest buildings in the world.

Inclusions: Segway tour, Professional guide, Thorough Segway orientation from a certified Segway trainer, Helmet and a bag on the Segway to store personal belongings

Exclusions: Gratuities

Reviewed By 355ron

We were in Chicago just for the weekend from Michigan. We decided to do the 2 hour lakeside tour and are so glad we did. it's a great excursion and our 13 year olds loved it. Our tour guide Cedar was really knowledgable and a joy to be around.

2. West Town Instagram Hot Spots Tour By Native 312

506 N Milwaukee Ave, Chicago, IL 60642, USA Native 312 Events
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5.0 based on 3 reviews

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene.

Inclusions: Tour Guide

Exclusions: Alcoholic Beverages

Reviewed By 185alexar

A great experience I would recommend to anyone! Having instructors to help and give techniques was helpful. I thought I wouldn’t be very good but anyone can be successful here.

3. Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

The Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL 60603, USA Babylon Tours Chicago
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5.0 based on 1 reviews

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour private guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol

Inclusions: Skip-the-Line Private Museum Tour , Professional Tour Guide Exclusively For You , Duration 2 - 2.5 Hours , Wheelchair Friendly, All Entrance Fees

Exclusions: Tour price does NOT include hotel pickup or drop-off (we recommend UBER or Taxi), Tour price does NOT include gratuities (optional)

4. Frank Lloyd Wright Robie House Admission

5757 S Woodlawn Ave, Chicago, IL 60637, USA Frank Lloyd Wright's Robie House
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4.7 based on 6 reviews

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the 20th Century Architecture of Frank Lloyd Wright List. Discover the residence Wright described as “a cornerstone of modern architecture” on guided tours that take in both the exterior and interior of the building. Inspired by the expansive landscape of the Midwest prairie, Wright’s Robie House is the most famous of the architect’s groundbreaking Prairie houses. Public tours are available Thursday - Monday. The museum is closed Tuesday and Wednesday. Save when you book directly at Visit to learn more.

Inclusions: Guide

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Reviewed By FUL-QWVR

Great guided tour. Our tour guide, Bob, was knowledgeable and pleasant. What an incredible cutting edge design for a house at the turn of the century. 120+ years later this residence is still awe inspiring. Sadly, there is only one piece of furniture in the entire house. Would have been nice to see a little more of the FLW designed furniture to give the full picture of this architectural icon. A little surprised at the lack of upkeep to the dandelion covered lawn and the stained rugs. Still a great visit.

5. Pilsen Walking Tour of Local Publicly Displayed Art

806 W Maxwell St, Chicago, IL 60608, USA Richard Blackmon

We find quality art from around the city by local artists that have significance towards local artists. Unique opportunity to appreciate homegrown art from local Chicagoans and to receive artistic inspiration.

Inclusions: All Fees and Taxes

Exclusions: Lunch is not included.

6. Wabash Arts Corridor Instagram Hot Spots Tour By Native 312

600 S Wabash Ave, Chicago, IL 60605, USA Native 312 Events

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene. Located in the heart of downtown Chicago, the Wabash Arts Corridor is the brainchild of Columbia College Chicago. The WAC is an urban outdoor exhibition featuring world class, large-scale works of public art. The heart of WAC is Wabash Avenue from Van Buren to Roosevelt and is framed to the east by Michigan Avenue and to the west by State Street. As an added bonus, this gallery is located amidst historical Chicago buildings with as story as colorful as the murals that don the exterior. Artists included in the tour: Collin van der Sluijs (Netherlands) Amuse 126 (Chicago) Justus Roe (Chicago) Renee Robbins (Chicago) Don’t Fret (Chicago) And many more!

Inclusions: Tour Guide

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Reviewed By 185alexar

A great experience I would recommend to anyone! Having instructors to help and give techniques was helpful. I thought I wouldn’t be very good but anyone can be successful here.

7. Pilsen Instagram Hot Spots Tour By Native 312

West 18th Street & South Paulina Street, W 18th St & S Paulina St, Chicago, IL 60608, USA Native 312 Events

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene. Pilsen owes its' name to the Czech population that emigrated here in the late 19th century, but is now home to one of Chicago's biggest Mexican populations and a hot bed for new & exciting art. The rich Mexican heritage can be seen throughout the neighborhood; everywhere from the Mexican Heritage Museum to the numerous murals found all throughout. Explore this neighborhood and it's rich culture new & historic with us.

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Reviewed By 185alexar

A great experience I would recommend to anyone! Having instructors to help and give techniques was helpful. I thought I wouldn’t be very good but anyone can be successful here.

8. Logan Square Instagram Hot Spots Tour by Native 312

1932 N Milwaukee Ave, Chicago, IL 60647, USA Native 312 Events

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our guide's extensive knowledge of Street Art and the local Chicago Art Scene. Murals by Artists on the Tour: JC Rivera Greetings From Tour Shawnimals Frank Quintero Sentrock And much more!

Inclusions: Tour Guide

Exclusions: All Fees and Taxes

Reviewed By 185alexar

A great experience I would recommend to anyone! Having instructors to help and give techniques was helpful. I thought I wouldn’t be very good but anyone can be successful here.

9. Art Institute of Chicago Skip-the-Line Guided Tour Semi-Private - Max 8 People

The Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL 60603, USA Babylon Tours Chicago

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour semi-private (8 Guest Maximum) guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol

Inclusions: All Entrance Fees, Duration 2 - 2.5 Hours , Semi-Private Means Group Size Is Never More Than 8 Guests Maximum, Wheelchair Friendly, Skip-the-Line Semi-Private Guided Museum Tour

Exclusions: Tour price does NOT include gratuities (optional), Tour price does NOT include hotel pickup or drop-off (we recommend UBER or Taxi)

Reviewed By marianmI3304CO

Our tour guide, Marlin, was a delightful and informative guide. We enjoyed every minute of our tour. Marlin was very helpful in ensuring that we had a wheelchair for my mother-in-law. Ask for Marlin you won't be disappointed in the least.

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