What to do and see in Chicago, Illinois (IL): The Best Cultural Tours

November 23, 2021 Myesha Cogley

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. Walking Tour of Lincoln Park in Chicago

The Children's Fountain, 2045 N Lincoln Park W, Chicago, IL 60614, USA Wild Onion Walks Chicago
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5.0 based on 4 reviews

Chicago's motto is Urbs in Horto: City in a Garden. On this tour, you'll see why. Stretching for 1,208 acres, Lincoln Park is the largest park in Chicago. You will explore a small portion of the park, but you'll see how Chicago has seamlessly melded natural beauty into the urban jungle.

Inclusions: Local guide

Exclusions: Food and drinks, Gratuities, Hotel pickup and drop-off

Reviewed By Carol Jean V

Amazing tour of this fascinating walkingtour of Chicago'sMagnificentMile. . My husband thought it would be about the retail shops, and was elated to find out this tour was more about Chicago's interesting history and the incredible architecture in this city. Kevin is an incredible historian, educator, and fantastic enthusiastic person. We highly endorse this walking tour.

2. Chicago Insider Segway Tour

300 E Monroe St, Chicago, IL 60601, USA Absolutely Chicago Segway Tours
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5.0 based on 26 reviews

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!

Inclusions: Live narration, Professional local guide, Helmet, and a bag on your Segway to store personal belongings, Thorough training and orientation session

Exclusions: Gratuities, Food and Drinks

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.

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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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. Boston Walk Through History Private & All-Inclusive Tour

Tremont St opp Temple Pl, Boston, MA 02108, USA ForeverVacation Boston
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Our Boston Walk Through History Tour will take you to the most historic spots in Boston in one day. If you are looking for a bit of delicious food, some great photos, and a ton of American History, then this is the tour for you. The morning will start with meeting with your friendly local guide. From there your tour will begin as you start your day walking through Boston and exploring the most historic landmarks in Boston. ==== Full schedule 9:00 AM- Meet your guide Park Street Station 9:15 AM- Arrive at Boston Common 9:30 AM- Arrive at Massachusetts State House 10:00 AM- Granary Burying Ground 10:20 AM- Mesmerizing Kings Chapel 10:45 AM- Learn about the Old South Meeting House 12:00 PM- Boston Massacre Site 12:15 PM- Lunch! 1:00 PM- Faneuil Hall Marketplace 1:30 PM- Go to Paul Revere's House 1:50 PM- The Old North Church 2:30 PM- Walk along Griffin’s Wharf 3:00 PM- Get dropped off by your guide at the Boston South Station

Inclusions: An Uber ride, English Speaking Tour Guide, All Fees and Taxes, Bottled water, Lunch

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Reviewed By Johnsavytravels6

Took this tour in early December as our last stop in the US. What a great tour and great food in Boston. Ask for Robin as your guide. She was so nice and answered all of our questions about Boston. Loved how this tour was private so we could go at our own pace. Highly recommend!

5. Chicago Private Tours

Chicago Private Tours
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4.9 based on 133 reviews

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 4 PASSENGERS TOTAL.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more.  The tour will be interactive and entertaining, covering history, architecture and culture.  We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

Inclusions: Driver/guide, Local guide, Professional guide, Private transportation, Pick up at your Downtown Hotel

Exclusions: Gratuities

Reviewed By nchurik

These guys were great! They were very knowledgeable, adjusted on the fly and kept our day entertaining. I'll use them again!

6. Chicago Walking Tour: Historic Treasures of Chicago

Chicago Architecture Center, 111 E Wacker Dr, Chicago, IL 60601, USA Chicago Architecture Center
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4.8 based on 12 reviews

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this tour. After the World's Columbian Exposition of 1893, Chicago was determined to become a great cultural and commercial metropolis. This tour is a testament to that era's ambitions. See buildings by Daniel Burnham, Louis Sullivan, Holabird and Roche and other noted architects and hear the stories behind the city's architectural gems.

Inclusions: Walking tour of Chicago Architecture, Narration by a professional and certified guide

Exclusions: Hotel pick-up or drop-off, Storage for luggage or strollers, Coat check

Reviewed By FUL-QWVR

Good variety of architectural items for sale. From books and clothing to mugs and artwork. I really enjoyed browsing their shelves and enjoyed seeing the Chicago architectural memorabilia. Staff was very pleasant. We didn’t take any of the tours so I can’t speak to their quality.

7. Chicago Walking Tour: Art Deco Skyscrapers

30 N LaSalle St, Chicago, IL 60602, USA Chicago Architecture Center
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4.7 based on 71 reviews

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco and its hallmark motifs while admiring buildings like the Chicago Board of Trade, One LaSalle Street and the Field Building (now the Bank of America Building) -- all of which are designated Chicago landmarks.

Inclusions: Walking tour of Downtown Chicago Art Deco architecture, Narration by a professional and certified Guide

Exclusions: Hotel pick up and drop off, Storage for luggage or strollers

Reviewed By FUL-QWVR

Good variety of architectural items for sale. From books and clothing to mugs and artwork. I really enjoyed browsing their shelves and enjoyed seeing the Chicago architectural memorabilia. Staff was very pleasant. We didn’t take any of the tours so I can’t speak to their quality.

8. 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.

9. Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner

The Chicago Theatre, 175 N State St, Chicago, IL 60601, USA Chicago Personal Neighborhood Tours

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighborhoods in Chicago. Some tours show 1 or 2 neighborhoods, we travel through the South Side, North Side, Southwest, Northwest and a portion of Downtown showing more then 10 neighborhoods and attractions. Our tour includes 3 meals from 3 Chicago local eateries.

Inclusions: Price includes coffee/tea and a pastry at a local Chicago coffee shop Robust Coffee shop in the Woodlawn neighborhood., Headphones to hear guide., Phone charging port., Price includes Chicago Style Hot Dogs, Italian Beefs and other Chicago staples in Chicago’s Little Italy neighborhood., Price includes Chicago style deep dish pizzas and other menu items from Home Slice in the beautiful Lincoln Park. Excludes alcohol, passengers to cover alcoholic drinks.

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