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Chicago Highlights: Architecture & Food Tour
4.9
1,009 Ratings
Chicago
Embark on an epic Chicago day tour with a local guide. Explore the city’s architecture, indulge in delicious local treats, and soak in stunning river views.
Embark on an epic Chicago day tour with a local guide. Explore the city’s architecture, indulge in delicious local treats, and soak in stunning river views.
Duration:
4 hours, 30 minutes
Cancellation:
24 hours
Highlights
- The Chicago Theatre - Start the journey beneath the iconic Chicago Theatre marquee, renowned from films, before venturing into the vibrant city streets.
- Chicago Pedway - If the weather allows, explore the Chicago Pedway, a series of underground tunnels frequented by locals and commuters, especially during winter.
- **City of Chicago - City…
- The Chicago Theatre - Start the journey beneath the iconic Chicago Theatre marquee, renowned from films, before venturing into the vibrant city streets.
- Chicago Pedway - If the weather allows, explore the Chicago Pedway, a series of underground tunnels frequented by locals and commuters, especially during winter.
- City of Chicago - City Hall - Pass by the City Hall-County Building, which houses the City of Chicago and Cook County governments.
- Chicago River - Experience the local vibe as you walk past famous buildings, admire breathtaking skyline views, and join the daily commute along Chicago’s main thoroughfare.
- Wrigley Building - Continue to the Wrigley Building on the Magnificent Mile, constructed between 1920 and 1924 as the Wrigley Company’s headquarters.
- Tribune Tower - Proceed to the Tribune Tower, a 463-foot, 36-story neo-Gothic skyscraper located at 435 North Michigan Avenue.
- Millennium Park - Visit the scenic Millennium Park, home to the renowned Bean sculpture. The guide will provide suggestions for additional attractions, dining, or drinks.
- Cloud Gate - Pass by the Cloud Gate sculpture, affectionately known as ‘The Bean,’ the highlight of Millennium Park.
- The Loop - Conclude with a stroll through the main streets near the Loop, where museums, eateries, bars, historic sites, and contemporary architecture converge.
What's Included
- Hear stories of Chicago’s past — from Prohibition to the Great Fire and immigrant history
- Explore top sights & hidden gems — Riverwalk, Magnificent Mile, Pedway, Wrigley Building
- Taste Chicago’s iconic eats — deep-dish pizza, hot dog, Italian beef & more included
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Led by expert local guides — passionate storytelling from true Chicago insiders
-…
- Hear stories of Chicago’s past — from Prohibition to the Great Fire and immigrant history
- Explore top sights & hidden gems — Riverwalk, Magnificent Mile, Pedway, Wrigley Building
- Taste Chicago’s iconic eats — deep-dish pizza, hot dog, Italian beef & more included
- Led by expert local guides — passionate storytelling from true Chicago insiders
- Enjoy a personal, relaxed, and interactive experience - Small group size (max 12)
- Travel for good — run by a certified B Corp committed to ethical, responsible tourism
- Visit Millennium Park & The Bean — snap pics at Chicago’s most famous modern landmark
What's Not Included
- Gratuity
- Drinks and additional food
- Gratuity
- Drinks and additional food
Additional Information
Explore Chicago’s fascinating history and lively food culture on this engaging walking tour. Experience the city’s renowned architecture and the allure of the Prohibition era while enjoying delicious local dishes. From deep-dish pizza to hidden treasures, relish the tastes of Chicago as an expert guide reveals the city’s culinary delights and intriguing…
Explore Chicago’s fascinating history and lively food culture on this engaging walking tour. Experience the city’s renowned architecture and the allure of the Prohibition era while enjoying delicious local dishes. From deep-dish pizza to hidden treasures, relish the tastes of Chicago as an expert guide reveals the city’s culinary delights and intriguing past.
- This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.
- Please note: food options and portion sizes will vary depending on the season and where we stop that day but the total amount of food included will be equal to a full meal.
- Suitable for all ages and fitness levels, but please note that this tour covers between 4.8 to 6.4 km (3-4 miles) of walking.
- We can accommodate vegetarian options but cannot accommodate other food allergies or dietary preferences. Please notify us in advance if you have any dietary requests.
- Experiences happen rain, shine, or snow. Please dress accordingly.
Location
The Chicago Theatre
North State Street
The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.9
(1009 Ratings)
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Holliebtrex
May 6, 2025
Rich makes travelers family! - First Rich learned all of our names and where we were from. This was only the beginning of a tour that felt like traveling with family instead of strangers. From pointing out Tiffany Glass ceilings to helping with Chicago deep dish pizza it was a learning experience. Well worth the time and even more worth the money!!!
Review provided by Tripadvisor
Whyrobertmack
May 3, 2025
A Perfect Way to Explore Chicago – Dash Was Incredible! - We did the “Chicago in a Day” tour and it was truly one of the best ways to experience the city, especially if you’re short on time. Our guide, Dash, was fantastic—full of knowledge, energy, and enthusiasm. He made the history and culture of Chicago come alive through engaging stories and a deep understanding of the city’s architecture and local life.
The tour had the perfect balance of walking, learning, and eating. We explored iconic landmarks, discovered hidden gems I never would have found on my own, and made several delicious food stops along the way. The pace was just right—not rushed, not too slow—and the five hours flew by.
As someone visiting for only a couple of days, I felt like I saw 20 to 30 hours’ worth of sights and learned so much, all in one well-organized and fun experience. For the value, this tour was absolutely worth it, and I’d recommend it to anyone visiting Chicago. Ask for Dash if you can—he made it extra special!
Review provided by Tripadvisor
Sharonp893
May 3, 2025
Awesome tour! Definitely recommend!! - Actually, 5 is too low! I wud rate the tour a 10+!! Dave is awesome! He know Chicago & went into detail about the places, architecture, area, took us into various buildings, history of Chicago, the Chicago Fire, the Bean, the Park, the beautiful library, the old Sears building, Marshall Fiels (Macy) store, the El train (Road & got off @ Quincy), Garrett’s pop corn & so many more stops & sites. The tour is a walking tour so wear very comfortable shoes & clothes. There are plenty of bathroom stops that are clean. We had the famous Chicago hot dog, the Italian beef sandwich & deep dish pizza. Very filling. Dave was very accommodating to any dietary needs or allergies. I would definitely recommend this tour to learn about Chicago, the area & its sights. Hopefully you will get Dave & will not be disappointed! Thank you Dave for a fabulous day!!
Review provided by Tripadvisor
M1516ifyvettec
Apr 29, 2025
Great Day in Chicago with Rich - We had such a great experience on the Chicago in a Day tour with Rich! He was so knowledgeable and made learning about the city's history, architecture, and food really fun and interesting.
We brought our three young boys along, and Rich was wonderful with them super patient, engaging, and made sure they felt included the whole time. It’s not always easy keeping kids interested on tours, but he really made it fun for them too.
You can tell Rich loves Chicago and loves sharing it with others. His stories and facts brought the city to life in such a fun way. The food stops were also delicious he gave great recommendations!
If you’re visiting Chicago, definitely book this tour, and if you get Rich as your guide, you’re in great hands.
Our kids wanted to give him 10 stars! Highly recommend!
Review provided by Tripadvisor
A9296lkpietroc
Apr 27, 2025
ALL GOOD;) - The view is beautiful the food is great the desserts great the beautiful place the nice waiters and always available and I had so much fun
Review provided by Tripadvisor
P3632xnanaisg
Apr 25, 2025
Fantastic tour!! - Chicago Dave is the best!!! He was personable, accomodating, knowledgeable and very funny. I learned so much about Chicago and it's history. The tour was 5 hours but felt like it was over so quickly. I definitely want to come again with my husband and kids. They would love it!
Review provided by Tripadvisor
Inspire37012940764
Apr 16, 2025
Incredible Chicago experience ! - An incredible day! Our tour guide Dash was so insightful , funny and made the experience really memorable ! Wonderful tour and great food and company ! Highly recommend!
Review provided by Tripadvisor
Voyager12529859423
Apr 16, 2025
What an Introduction! - Amazing way to start our trip. Dash did an incredible job of introducing us to the history, art, architecture, and food of this great city. I would recommend this tour a thousand times over. What a great day!
Review provided by Tripadvisor
Michelle_u
Apr 15, 2025
Informational,... - Informational, well-paced. There was something for everyone in my family with both architecture and food
Review provided by Viator
Sasha_g
May 4, 2025
great way to spend the day - chicago dave has clearly put a lot of thought into the flow and design of the tour - we loved seeing chicago scenes from famous movies, that was a great added element.
Review provided by Viator
