Explore Chicago’s Iconic Architecture and Culinary Scene on a Private Tour

Private From Architecture to Food Tour

Duration: 5 hours Price per group: Starting at $396

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!

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Please Note: Due to current COVID-19 restrictions, all dining will be outside. Please dress accordingly for Chicago winter weather.

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General Itinerary

Ready for the ultimate day out in Chicago? This tour combines two of our favorite Chicago experiences (Chicago Culture & Architecture and Classic Bites in River North) for one epic Chicago adventure!

We start our tour under the dazzling marquee of the Chicago Theater (where you might recognize the neon sign from the movie musical Chicago). We’ll then head off into the bustling city where our first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core.

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. 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.

Next, we’ll make our way to a spot where we’ll share a sweet treat, and a local tradition: Chicago-style popcorn. 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).

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! Once we’re back on solid ground, we’ll make our way to another delicious destination for locally made chocolates from a Chicago staple.

Next, we’ll take a stroll through the beautiful lakefront parks along Michigan Avenue. We’ll end up in the picturesque Millennium Park, home to the iconic Bean sculpture.

We hope you’ve built up a good appetite by now because we’re on our way to an unforgettable food experience. Travel by ‘L” train or ride share with your guide from Millennium Park up to the River North neighborhood, the original Chicago foodie destination.

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.

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Additional Information

Inclusions: Local, English-speaking guide, popcorn tasting, chocolate tasting, water taxi or "L" ticket, transportation between tour halves, and a variety of food samples (such as a Chicago-style hot dog, deep dish pizza, and Italian beef).

Exclusions: Additional food or drinks, souvenirs and personal shopping, tips/gratuities for your guide.

Notes:

• Please dress comfortably and casually in weather-appropriate attire. Wear comfortable shoes for walking.
• This tour runs year-round and will proceed rain or shine unless such weather constitutes a dangerous situation.
• In the event of road or attraction closures, your guide will do their best to work around the obstacles or take your tour to alternate locations.