Total Chicago: From Architecture to Food
Chicago, USA
From USD 99.00
Office phone number: +1 312 973 3877
Total Chicago: From Architecture to Food
Chicago, USA





Culture shock rating
Worried we’re going to shock your senses? Relax! We believe part of the fun of travel is immersing yourself in the destination and its culture, meeting the people, and learning what makes the place tick. We’ve got a wide range of tours with something for everybody. The cultural shock rating ranks how different the experience is from most Western cultures. But no matter the level, don’t worry, you’ll have a local, in-the-know guide with you every step of the way.
Low
Consider these tours your 101 intro to a place. Transportation might be private or a very comfortable public option, and the activities are usually visits to iconic sites and locations that are familiar to most Western cultures – but that will still give you fantastic insight into a destination.
Medium
Expect to rough it for parts of this tour, whether that’s on a packed public bus or in a local market off the tourist trail. There might be a few language barriers or unfamiliar cultural customs, and you’ll get an experience different from what you're used to at home.
High
You're out there in the global community! We’re going to take you down streets you’d rarely explore on your own, introduce you to local customs and languages, and take you for a ride in whatever transport is available. Get ready to take it as it comes, whatever comes. There might be a shock, but oh man, it’s worth it.

Physical rating
Worried our tours are too tough? Relax! From leisurely strolls to muscle-burning treks, we’ve got a wide range of tours with something for everybody. The physical grading gives you an idea of how much huffing and puffing you can expect on the tour.
Low
Slow and steady is all you need here. These tours have very limited physical activity, such as walking relatively flat streets, sites, or markets, and climbing in and out of the transport provided.
Medium
Not too hard, not too soft, these tours are just right! You can expect a bit of physical activity, but nothing overly challenging – perhaps walking up and down hills, riding a bike for up to 30 kilometers along mostly flat terrain, or jumping in a kayak for a gentle paddle on flat water.
High
Get ready for a workout! These tours are our most challenging and involve intense walking, hiking, kayaking, swimming, or bike riding. You could be making steep climbs by foot or pedal, or working your core in the water. We recommend you have a good level of fitness to join this tour.
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Tour snapshot
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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Highlights
- 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
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Schedule details
- Duration: 5 hours
- Meeting point:
The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601
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- Starting time: 10.00 AM
- Ending point:
A central location in the River North neighborhood near the Chicago Brown Line “L” Station.
Language: English
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 and drinks, tips/gratuities for your guide.
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 and drinks, tips/gratuities for your guide.
Dress standard: Please dress comfortably and casually in weather-appropriate attire. Wear comfortable shoes for walking.
Your Trip: For your Urban Adventure you will be in a small group of a maximum of 12 people.
Confirmation of booking: If you have your voucher, your booking is confirmed. We'll see you at the start point. Get in touch if you have any concerns or require more information via the email address or phone number (business hours only) on your voucher.
Additional Information: This tour runs year-round and will proceed rain or shine unless such weather constitutes a dangerous situation.
Closure of sites: 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.
Child Policy: This is a child-friendly tour. Children between the ages of 6 and 11 inclusively are permitted on this tour at the rate listed above. Please select ‘child’ above when booking. Children under the age of 6 are permitted to join this tour free of charge. Please inform us at the time of booking if you’ll be bringing a child under the age of 6. You can do so in the special request box on the checkout page.
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Dietary Notes
We can accommodate vegetarians and other dietary restrictions. Please notify us in advance if you have any dietary requests. You can do so in the ‘Additional information’ box at checkout, or by emailing us at info@chicagourbanadventures.com.
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Local contact
Office phone number: +1 312 973 3877
Email address: info@chicagourbanadventures.com
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