Chicago Day Tour: Food, History, Architecture

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treat and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

Duration: 5 hours
Cancellation: 1 day learn more
Highlights
  • The Chicago Theatre - Our tour kicks off beneath the iconic marquee of the Chicago Theatre, a familiar sight from numerous films and TV shows, before we venture into the lively city.

  • Chicago Pedway - If the weather is favorable, we’ll make our way to the Chicago Pedway. This distinctive feature of the city is a network of underground tunnels used daily by locals and commuters, especially during the harsh Midwest winters.

  • City of Chicago - City Hall - We’ll pass by the City Hall-County Building, commonly referred to as City Hall, which houses the government offices of both the City of Chicago and Cook County.

  • Picasso Statue - Our next stop is the Chicago Picasso sculpture by Pablo Picasso in Daley Plaza. Installed in 1967, The Picasso marked a significant shift in civic and urban planning, expanding the concept of public art beyond mere commemoration.

  • Chicago River - Feel like a local as you zip past buildings and take in more stunning views. If your guide opts for a water taxi, you’ll experience the Chicago skyline from a unique vantage point, sharing in the daily commute of Chicagoans.

  • Chicago Riverwalk - This award-winning $150 million, 1.25-mile promenade along the south bank of the Chicago River downtown offers breathtaking views. Weather permitting, we’ll stroll along the Riverwalk, admiring several towering buildings like Marina Towers, the Wrigley Building, and the Chicago Tribune.

  • Wrigley Building - We’ll pass the Wrigley Building, located on the Magnificent Mile directly across Michigan Avenue from the Tribune Tower. Its two elaborate towers, built between 1920 and 1924, originally housed the Wrigley Company’s corporate headquarters.

  • Tribune Tower - We’ll pass by the Tribune Tower, a 463-foot-tall (141 m), 36-floor neo-Gothic skyscraper at 435 North Michigan Avenue.

  • The Magnificent Mile - We’ll pass through the Magnificent Mile, a premier commercial district in downtown Chicago. Part of the 1909 Burnham Plan, this area was transformed in the 1920s from an industrial and residential zone into a bustling hub of shops, restaurants, hotels, and attractions on North Michigan Avenue.

  • Chicago Cultural Center - Step inside this Chicago Landmark building, managed by the Department of Cultural Affairs. The Cultural Center serves as the city’s official reception venue, where the Mayor of Chicago has welcomed presidents, royalty, diplomats, and community leaders.

  • Millennium Park - Next, we’ll visit the picturesque Millennium Park, home to the iconic Bean sculpture. Here or nearby, your guide will conclude the tour and provide recommendations for more sights, lunch spots, or drinks.

  • Cloud Gate - We’ll pass by Cloud Gate, a public sculpture by Indian-born British artist Anish Kapoor, which serves as the centerpiece of AT&T Plaza at Millennium Park in the Loop community area.

  • River North - Your food tour begins with a classic Chicago treat: the Chicago-style hot dog. Every local has their own preferred way to make it, and you’ll get to try your guide’s favorite version.

Next, indulge in the world-famous Chicago deep-dish pizza! This hearty dish, a staple of Chicago’s food scene, originated in River North in the 1940s to provide filling meals at low prices. Your guide will take you to a beloved local pizzeria to sample the authentic version.

After enjoying pizza and hot dogs, we’ll visit two more essential establishments in Chicago’s food culture. Our tasting journey continues with a classic Chicago sandwich: Italian beef. You’ll sample this sandwich at a true Chicago institution, complete with no-frills decor.

  • Historic Water Tower - We’ll pass by the beautiful water tower, built in 1869 to house a large water pump drawing water from Lake Michigan. It is the second-oldest water tower in the United States.
  • The Loop - Stroll through the main streets near the Loop, where you’ll find a unique blend of museums, restaurants, bars, historic landmarks, modern architecture, shops, and art galleries.
What's Included
  • Transportation between tour halves
  • Taste Chicago’s famous food like Chicago-style hot dog
  • Try Deep dish pizza at an iconic Chicago pizza place
  • Join professional English-speaking local guide
  • Discover Chicago on 4 Food Stops with 4 Food Samples
  • Get tips on what else to see, do and eat during your stay
  • Discover Chicago’s incredible architecture both old and new
  • Enjoy classic Chicago-style popcorn
  • Taste a classic Chicago sandwich: Italian beef
What's Not Included
  • Gratuity
  • Drinks and additional food
Additional Information
  • 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.

Customer Ratings
4.9
(847 Ratings)
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Xavier_g
Jul 29, 2024
It was simply amazing - It was a great way to immerse in Chicago for first timers. In 5 hours our guide gave us a huge amount of knowledge, shared experiences in a fun and didactic way. Special thanks to Dash, our guide. I have had many of these tours booked from Viator and he makes easily the top 1. I would totally recommend this tour. Best money spend.
Review provided by Viator
Brittany_v
Jul 28, 2024
Fun, educational, will not leave hungry! - If there is one thing our tour guide Dash taught us, it was to always look up in Chicago. He taught us how to tell what era buildings were built based on their appearance and showed us so many places where beautiful artwork covered the ceilings. I love that we got to eat at some of Chicago’s hot spots without the wait, and even my 5 year old enjoyed the Chicago dog!
Review provided by Viator
Trail716113
Jul 28, 2024
Wonderful day exploring Chicago - Dash was a fantastic guide! So much interesting information about Chicago delivered with so much enthusiasm. He made this trip worth every penny. Definitely recommend 👍 we learned tidbits that even locals don't know, had time for photos, tried famous treats/ lunch, had quick bathroom breaks too during this 5hr tour. Loved it, thanks Dash!
Review provided by Tripadvisor
A8380szpaulg
Jul 27, 2024
Worth the time and money - We had a great time with Chicago Dave who was a attentive and knowledgable host. The food was excellent and the architecture was amazing. We would definitely have missed 3/4 of the interesting places without the guidance from Dave. There is so much to see in Chicago and I would recommend the boat tour and the bus tour in addition to this walking tour. That said we are glad we went with Dave and I would highly recommend this tour as an excellent way to orientate yourself with the Loop area.
Review provided by Tripadvisor
452ericah
Jul 26, 2024
Fabulous tour! - We absolutely loved out tour with Dash! He was incredibly nice, entertaining and knowledgeable. The first half of our tour was a great walk around downtown learning about the different architecture and industry of this city. The second half was the food tour and everything was delicious! It is all fairly meat forward, so vegetarians may need to consider that.
Review provided by Tripadvisor
K5415cerobertf
Jul 23, 2024
So glad we chose this tour - Really enjoyed this tour. Dave is an amazing guide. Not only does he give you a good mix of history, hidden gems and fun facts but his genuine enthusiasm and passion for the city is infectious. Highly recommend.
Review provided by Tripadvisor
Mateypatatey
Jul 23, 2024
Beautiful city. Great food. Brilliant guide with Chicago Dave - The tour was fantastic mostly due to our guide Chicago Dave who seemed to know almost everyone in Chicago. The city is beautiful, the food was delicious and more than we could eat even with a big walk and the stories from Dave about Architecture, History and people really made our day. Highly recommend taking the tour you cannot see as much of the city in this depth on your own.
Review provided by Tripadvisor
A7878nealicer
Jul 22, 2024
An excellent tour - This was a great introduction to Chicago. Our tour guide Dave was very knowledgeable on Chicago, and answered all our questions. We enjoyed learning about the history and architecture of chicago and enjoyed the food also! I highly recommend this tour.
Review provided by Tripadvisor
656deepaks
Jul 20, 2024
Incredible walking and food tour of Chicago - We spent a very enjoyable and informative 5 hours with Dash learning the history and enjoying the beautiful architecture and delicious food of Chicago. Dash is quite enthusiastic and does a terrific tour—which was exactly what we needed on our 1st day in this amazing town.
Review provided by Tripadvisor
Antwanette_s
Jul 16, 2024
A must do!! - Dave was extremely knowledgeable and kind. It was my first time in Chicago and I learned so much. He took the time to explain the architecture surrounding each stop as well as historical facts about the city. The food & snacks provided along the way was definitely a plus! A must do if you’re a first timer like myself!
Review provided by Viator
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up to 9 guests
1 Adult
September 2024
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