Highlights & Hidden Gems of Chicago in Chicago - pexels-eric-esma-876218_1
5.0

Highlights & Hidden Gems of Chicago

  • 3 hours
  • City Highlight Tours
  • Chicago
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Choose one of 2 locals available

Experience hosted by Colm & Mike

  • Private Tour
  • Carbon Neutral

Want to see the best of Chicago? We got you covered. But as you can expect from a Withlocals experience, the real excitement is its hidden gems. Join your favorite local and get a feeling of the city's real vibe on a tour that has it all, so you can say: I experienced the real Chicago!

Destination
Chicago, United States
Category
City Highlight Tours
Duration
3 hours
Transport mode
Walking tour
Available languages
English
Included
  • Private Guide
  • 1 Local Drink or Snack
  • All Withlocals Tours are Carbon Neutral
Excluded
  • Entrance to attractions

6 reasons to book this tour

  • Explore the best of the city in only 3 hours
  • Spot classics like The Bean & Art Institute of Chicago
  • Discover hidden gems away from the tourist paths
  • Experience the city from a local’s perspective
  • Can be 100% personalized to your wishes
  • Privately guided by a local expert

What you can expect

Highlights & Hidden Gems of Chicago in Chicago - pexels-eric-esma-876218_1

Chicago, is a magical place! And with the local host of your choice, you are going to experience it all. So get ready; culture, history, and local lifestyle await!

Dive into the origin of Chicago as you see the city’s main landmarks like The Bean, Art Institute of Chicago, and Riverwalk. And how about the hidden gems? Oh, you’re in for a surprise! Every host has its own story to tell, so pick your favorite, and you’ll discover the city through their eyes. Experience their Chicago to the max based on their passions and expertise. They’ll make sure you have fun enjoying a unique and local perspective of Chicago.

Want to take a break? Leave it up to your host! This is the perfect opportunity to visit that special eatery where only the locals come and your chance to enjoy a local treat hand-picked by your host. Feel free to ask your host more about their life in their city or get recommendations about the top things to do in Chicago. Remember, the locals know best.

The best part of any city tour is definitely the unique stories. Everybody has a story to tell, especially your host. Each one of the local hosts has a different background ranging from arts to history. They can’t wait to share their knowledge with you and exchange ideas and perspectives! Feel like changing the route a bit? No problem, the hosts will be happy to personalize the tour to your wishes and make their Chicago, your Chicago!

Choose your local

Get to know these 2 passionate locals, each bringing unique perspectives and talents. Choose your favorite, check their availability, and book to create an unforgettable adventure tailored to you.

  • Colm - Friendly Chicago Walking Guide

    Colm

    Friendly Chicago Walking Guide

    5.03 reviews
    English
  • Mike - Making architecture, design, & history fun & interesting!

    Mike

    Making architecture, design, & history fun & interesting!

    5.09 reviews
    English

This is the plan

Check out the plan below to see what you'll get up to with your local host. Feel free to personalize this offer with the host of your choice.

  1. Meeting point

    Meet at Under the Chicago Stock Exchange Arch on the corner of Monroe and Columbus - Chicago to start your journey

  2. Itinerary

    This is what our experience could look like, but it’s not set in stone! Once you book, you can chat directly with your host to make small tweaks to suit your preferences.

  3. City Highlights

    See from The Bean, Art Institute of Chicago, Riverwalk, and other landmarks and must-sees of the city. Your local host will take you to the main spots in town so you can get the perfect overview of what makes Chicago so unique

  4. Hidden Gems

    Along the way, your local host will show you treasures hidden in plain sight that only the locals know about. Get to know the city through a different perspective, the local way, and discover places and stories that not many tourists experience

  5. Magical Storytelling

    Behind every landmark and every stop, there’s a story, and your local host is ready to tell it all. Get ready to listen to incredible stories, one-of-a-kind insights, and fun facts only a knowledgeable local would know!

  6. Special Treat

    Follow your host to one of their favorite eateries for a snack or a drink beloved by the locals. Take a break and catch up with your new local friend and get the answers to all your travel questions

  7. Make it yours

    Want to tweak the itinerary? Book directly & chat afterwards with your host to adjust highlights, skip stops, or make small changes to fit your preferences.

    Book risk-free: Cancel within 24 hours for a full refund.

    Need something special? Personalize your experience for more time, alternative locations or a completely tailored plan.

Flexible cancellation policy

  • Feel confident booking

    Cancel within 24 hours for a full refund. Even up to 7 days before your experience, you’ll receive a refund, minus the service fee.

  • Change of plans?

    Reschedule your experience to a date and time that works best for you.

  • Loved by travelers worldwide

    Simple and flexible – your plans, your way.

Reviews from guests

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Louise
(About local )
15 October 2024
Mike was a fantastic guide and very informative. Would thoroughly recommend this tour. We went to places we would never have found on our own. Faboulous Chicago Tour
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gimaklein🇬🇧 United Kingdom
(About local )
15 November 2023
Our tour with Mike has been excellent - a great way to explore Chicago! Mike is extremely knowledgeable about all things history, culture and architecture of the city. Even more importantly, he is extremely nice and easy-going, so time flew. We highly recommend Mike! Wonderful experience in Chicago
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Dawn🇺🇸 United States
(About local )
17 September 2024
We enjoyed our time with Mike and learned so many interesting facts about history and architecture of Chicago! Excellent Walking Tour of Chicago!
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Jo🇨🇦 Canada
(About local )
20 April 2024
Wow....What a smart guy!!! My friends and I loved our time spent with Colm. He met us promptly at our hotel and deposited us directly at the restaurant (he recommended) 3 hours later. Colm was able to tell stories that brought much of what we saw to life. (Ask him about seeing Obama arrive for jury duty). He was also able to hold the attention of 3 very enthusiastic and chatty women! Colm was easy to reach so we could confirm details about our trip and adjusted our tour to US! Thanks Colm!!! Wonderful walk around the loop with Colm!
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Michelle🇺🇸 United States
(About local )
26 September 2023
I made a special request tour of Chicagoland with Colm to show us around town and neighborhoods and it was a must-do experience!! Will be relocating my newly graduated kid to Chicago (23 yrs old) and needed a crash course in neighborhoods,CTA transit, demographics, living in Chicago, orienteering and advise. Colm has it all!! He met us at my hotel, and we started the day at State and Madison - which is the "zero point" address for the city and for navigating Chicago overall. All public transportation for entire 5 hour tour. Embarked to several neighborhoods and walked around to get the vibes. Wrigleyville, Southport, Lincoln Park, Old Town, River North and Wicker Park...That's 7 neighborhoods people!! Colm has extensive knowledge and fun facts for every stop. Had a super informative and totally fun day. When time permits - will be seeking more tours with Colm. Newcomers Must-Do City Neighboorhood Tour
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Dana 🇺🇸 United States
(About local )
8 September 2023
I highly, highly recommend Colm for a tour. He’s very informative with lots of great details and knowledge about the paintings, the museum and city as well. I have been to the Art Institute many times. This time, my friend who has an MFA in painting, was in town so I wanted an expert to show us around. Colm’a tour was really a special few hours. He knows the museum so well and we saw staggering number of famous works this museum has. It was the highlight of my friend’s visit and a huge highlight for me as well. I highly recommend. Great tour!
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Shawn
(About local )
12 April 2023
Mike is amazing. He knows Chicago like the back of his hand. I had never been there and I took photos of the exact things I had wanted to. Mike is patient, warm and kind. He's also funny with great energy. I wouldn't hesitate to recommend his tours!The best photo opportunities!
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Pat
(About local )
5 April 2023
Chicago's Neighborhoods - Chinatown An excellent tour. It's unlikely I'll ever be able to spend any time in Chicago but I really enjoyed walking through the Chinatown neighbourhood with Mike!!Excellent and very worthwhile!
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Chris
(About local )
8 March 2023
This is our second tour with Mike, but definitely not our last! The two-hour tour is jam-packed with interesting and well-researched information. Even as native Illinoisans, there was a lot of new anecdotes and perspectives to consider. Highly recommend for native Chicagoans AND visitors alike! Mike has such a friendly and easy-going way of presenting the information and I just love his unique takes on buildings that I've walked past dozens of times.For Native Chicagoans and Visitors Alike
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Chris
(About local )
2 March 2023
My husband and I went on this tour because we thought it was a unique concept. Money well spent! Not only was this highly entertaining, but Mike was super knowledgeableDefinitely repeat customers!
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Rob
(About local )
1 March 2023
We just did our second Tour With Mike, this time the Underground Chicago tour. Really fun. We explored the bowels of the city, from familiar spots like the Billy Goat on Lower Michigan to portions of the labyrinthine Pedway. I've lived here over 30 years and saw some things I've never seen before. Mike is great. Knowledgeable, friendly, engaging. He's a fantastic tour guide for visitors and longtime residents alike. Thank you!A Must for Visitors & Locals, Too
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Judy
(About local )
4 February 2023
Awesome Tour - fantastic blend of architectural knowledge, Chicago history and entertainment - Mike does a great job making this tour fun - and a great value! We will use his tours again in the future!Excellent Tour - Highly Recommended

Withlocals experiences
are always

Private & personalizedNo strangers, just you. Fully customize your trip to your needs.
With a local expertFrom historical facts to the most up-to-date health regulations.
Without the crowdsExperiences designed to take you away from the crowds towards authentic local spots.

Other City highlight tours in Chicago

€113.97per person