Chicago in a Day: Food, History and Architecture Combo Tour

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Activity Highlights
This is a typical itinerary for this product

Stop At: The Chicago Theatre, 175 N State St, Chicago, IL 60601-3623

We start our tour under the dazzling marquee of the Chicago Theater (where you might recognize the neon sign from the movie musical Chicago) before heading off into the bustling city.

Duration: 10 minutes

Stop At: Chicago Pedway, Chicago, IL

We’ll then head towards the Chicago Pedway. This unique feature of Chicago is used by locals and commuters daily to move about the city in a network of underground tunnels — especially necessary during the Midwest winters. We’ll head back above-ground near City Hall, and on most weekdays, be able to head inside to see the classic interior design and architecture.

Duration: 20 minutes

Stop At: Chicago Riverwalk, Chicago, IL 60601

Weather permitting, we’ll take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Sears Tower (now known as the Willis Tower).

Duration: 20 minutes

Stop At: Chicago River, Chicago, IL

From there, we’ll either hop on the ‘L’ train or a water taxi on the Chicago River (depending on the weather and time of year). Either option offers a uniquely local Chicago experience! The ‘L’ train is recognized as a Chicago landmark having been featured in movies and TV shows for decades. You’ll enjoy feeling like a local as you zip past buildings and catch even more awesome views.

Duration: 20 minutes

Stop At: The Magnificent Mile, North Michigan Avenue, Chicago, IL 60611

Finally, we’ll take a stroll through the beautiful lakefront parks along Michigan Avenue

Duration: 20 minutes

Stop At: Cloud Gate, 201 E. Randolph St. Millenium Park, Chicago, IL 60601-6530

We’ll end up in the picturesque Millennium Park, home to the iconic Bean sculpture. Here (or nearby), your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or a drink recommendation inside one of the most amazing spaces in the city.

Duration: 20 minutes

Stop At: Corporate Suites Network, 845 N State St, Chicago, IL 60611, USA

Your food tour starts with a very well-known Chicago fare: the Chicago-style hot dog. Every Chicagoan has his or her own preference as to how the dog should be made, and you’ll get a chance to try your guides’ favorite version.

Next up is the world-famous Chicago deep-dish pizza! An entire meal unto itself, this staple of the Chicago food scene originated in River North in the 1940s, when workers and families needed filling dishes at low prices. Your guide will take you to a pizza place that’s an icon to Chicago natives to try the real deal for yourself.

After you’ve filled up on pizza and hot dogs, you’ll take a stroll through two more establishments, each one essential to Chicago’s food culture. We’ll then continue our tasting journey with a classic Chicago sandwich: Italian beef. You’ll sample this sandwich in a real Chicago institution — no-frills decor included!

Our tour ends here, and your guide will be happy to direct you back to your accommodation or share tips for what else to see and do in the city.

Duration: 2 hours

Activity Details
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 treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

Marvel at the stunning Chicago skyline and discover why Chicago’s architecture is among the best in the world

Get around The Loop like a local: at street level, underground, elevated rails or perhaps even on the water

Enjoy a couple of classic made-in-Chicago snacks like Chicago-style popcorn and homemade chocolate

Get a taste for Chicago’s most famous food in one of the city’s most historic neighborhoods

Discover why locals have so much passion for their Chicago-style classics
Departure & Return
Departure PointThe Chicago Theatre, 175 N State St, Chicago, IL 60601, USA Departure Time10:00 AM
ReturnRiver North, Chicago, IL, USA
What's Included
  • Professional Local Guide
  • Popcorn Tasting
  • Chocolate Tasting
  • Water Taxi or Subway Ticket
  • Chicago-style hot dog
  • Deep dish pizza
  • Italian Beef
  • Entry/Admission - Chicago River
  • Gratuity
Additional Information
  • Confirmation will be received at time of booking
  • Wheelchair accessible
  • Stroller accessible
  • Service animals allowed
  • Near public transportation
  • Transportation is wheelchair accessible
  • Most travelers can participate
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This tour/activity will have a maximum of 9 travelers
  • Social distancing enforced throughout experience
  • Guides required to regularly wash hands
  • Paid stay-at-home policy for staff with symptoms
  • Contactless payments for gratuities and add-ons
  • All tours follow the latest local health authority advice, including mask usage and social distancing. Urban Adventures have received the World Travel and Tourism Council’s Safe Travels stamp, which recognises companies that have adopted health and hygiene global standardised protocols.
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveler Reviews

Average based on 18 reviews.

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  • Wriggly Bldg, Bridges over the River, History of Chicago Fire, Tunnels, Elav Train, The Bean. The Industrilists.

  • This was an excellent tour. I highly recommend the architecture and walking tour bit. It was a great way to see what the city offers considering the limited options available with all the Covid-related closures.

  • Dave was such a fun and excellent tour guide! This five hour tour flew by. He made every stop interesting and every food item we sampled was excellent! This is the perfect tour for your first time visiting Chicago.

  • It was a very expansive tour. Wallach was a great guide, informative and friendly . We learned and experienced so much - the history of Chicago, riding the subway, tasting the Chicago hotdog, pizza and Italian beef sandwich (all delicious), seeing amazing architecture and all of the highlights. A lot of walking but it’s the best way to experience all that Chicago has to offer.

  • Wallis did a wonderful tour of the city. He pointed out lots of interesting things about the city. Walked for hours, wear good shoes, food tour was a welcome relief

  • Wonderful tour!
    Very professional and personable!
    Even in the extreme cold took great care of us. Can't say enough good things about Wallach our guide.
    Very well done Urban Adventures!!

  • David is an excellent and a very friendly tour guide. He showed us some wonderful places in Chicago and made me fall in love with the city's architecture. And boy that deep dish pizza at the end of the tour, was just perfect finish to a morning well spent. Highly recommended.

  • Day started with rain, but quickly cleared and it was a perfect day for a stroll through the city. Laura knows the city and kept us entertained. She gave us a lot of insight and I’d even enjoy doing it again.

  • Our tour guide David was amazing and explained everything so clearly. Be prepared to walk alot so comfortable shoes are a must but it's worth it.

  • Very personal and informative tour. Learned the history behind the Architecture and famous sites in Chicago. Kelly-tour guide knew her history, was friendly and provided us with a great amount of information. The walking tour was scenic, good timing and good exercise.

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18 reviews
$102.3 USD
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Adult(s) upto 9 passengers
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