Chicago, the Windy City, is a vibrant metropolis known for its world-class museums, bustling nightlife, and stunning skyline. Withlocals offers unique experiences that allow you to explore the city like a local, from behind-the-scenes tours and intimate culinary experiences to outdoor adventures and more. Discover the hidden gems and local secrets of Chicago with Withlocals.
Chicago, the Windy City, is a vibrant metropolis known for its world-class museums, bustling nightlife, and stunning skyline. Withlocals offers unique experiences that allow you to explore the city like a local, from behind-the-scenes tours and intimate culinary experiences to outdoor adventures and more. Discover the hidden gems and local secrets of Chicago with Withlocals.
Always private. It’s just you and your local host. No strangers, no groups.
More you, less checklist
Let your local host tailor the experience completely to your wishes.
Travel that feels good
Our tours are designed with people, places, and the planet in mind.
Choose your favorite local
Highlights & Hidden Gems of Chicago
18 reviews
3 hours | City highlight tours | Chicago
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!
Step Back in Time: A Tour of Pullman's Company Town
5 reviews
4 hours | city highlight tours | Chicago
Get ready to take the train to visit America's first company town; Pullman, Illinois. Join me as we explore the town of Pullman and learn about the fascinating part it played in the development of the world's largest train company!
Your tour is just for you. No strangers, no groups.
You’ll experience the city one-on-one (or with your own travel group) in a relaxed, personal way. No rushing, no scripted group tours.
Tailored to your wishes
From highlights to hidden gems, your host adjusts everything to fit you.
Want to skip a museum, add a food stop, or focus on street art? Just ask. Every experience is shaped around your pace, preferences and interests.
Chat before you book
Message your host directly to customize your experience.
Ask questions, get local tips, or make special requests. Our hosts are real people, ready to make your day unforgettable.
Travel that supports locals
Every booking supports independent locals and their communities.
We believe tourism should benefit the people who live there. Your host earns directly and often invests it right back into their neighborhood.
Feel good about where your money goes
You’re choosing meaningful travel, not mass tourism.
Withlocals is built on fair pay, human connections and travel that leaves a positive mark for both you and the places you visit.
Trusted by millions
Loved by over 1,000,000 travelers all around the world.
Withlocals hosts consistently earn 5-star reviews for their kindness, knowledge and the personal stories they share.
Secure & flexible booking
Book with peace of mind: safe payments and easy changes.
Your plans can shift and that’s okay. We offer flexible cancellation and real support when you need it.
Private & Personal
Your tour is just for you. No strangers, no groups.
You’ll experience the city one-on-one (or with your own travel group) in a relaxed, personal way. No rushing, no scripted group tours.
Unforgettable experiences in Chicago with Withlocals
Withlocals tours are intimate, private experiences that allow you to truly connect with the city and your guide. No more being stuck on a crowded, generic bus tour, staring at a boring brochure - Withlocals brings the Windy City to life with personalized, authentic experiences. So come join us and let's discover the real Chicago together!
18 reviews
5 hours | City highlight tours | Chicago
Ready for a jam-packed tour, full of history, culture, stories, and sights? Checkmark from your travel bucket list all your must-sees of Chicago, because if there’s a Withlocals tour that shows you all the city's ins and outs, it’s this complete and personalized tour of Chicago.
From highlights to hidden gems, your host adjusts everything to fit you.
Want to skip a museum, add a food stop, or focus on street art? Just ask. Every experience is shaped around your pace, preferences and interests.
Chat before you book
Message your host directly to customize your experience.
Ask questions, get local tips, or make special requests. Our hosts are real people, ready to make your day unforgettable.
Travel that supports locals
Every booking supports independent locals and their communities.
We believe tourism should benefit the people who live there. Your host earns directly and often invests it right back into their neighborhood.
Feel good about where your money goes
You’re choosing meaningful travel, not mass tourism.
Withlocals is built on fair pay, human connections and travel that leaves a positive mark for both you and the places you visit.
Trusted by millions
Loved by over 1,000,000 travelers all around the world.
Withlocals hosts consistently earn 5-star reviews for their kindness, knowledge and the personal stories they share.
Secure & flexible booking
Book with peace of mind: safe payments and easy changes.
Your plans can shift and that’s okay. We offer flexible cancellation and real support when you need it.
Best Things to do in Chicago in 2026 - Withlocals
Travelers love our locals
Reviews from guests about our tours and locals
5.0
The Best Tour Guide in Chicago — Mike!
"We had an unforgettable experience exploring Chicago with Mike as our tour guide. His passion for the city’s culture, history, and hidden gems truly brought every moment to life. He didn’t just show us the iconic spots—he took us into incredible places, shared fascinating stories, and made the entire journey feel personal and meaningful.
From start to finish, the tour was engaging, fun, and full of insights we would’ve never discovered on our own. Mike is truly the best tour guide in Chicago, and we highly recommend him. If you’re visiting the city, don’t miss the chance to experience Chicago through his eyes!
Highly, highly recommended."
Cynthia About local MikeChicago, November 21, 2025
5.0
True Gent !
"Colm has a tremendous knowledge on Chicago and is happy to share it .
Very friendly chap with a passion for historic buildings , culture, interesting facts,hidden gems , and nice food stop offs.
Highly recommended 👌 "
"Mike offered us a wonderful overview of Chicago and its rich architectural history. He was very willing to tailor the experience to our interests. Highly recommend! "
"We did a three hour walking tour with Colm and had a great time! We learned so much and had a lot of fun along the way. Colm has a great way of storytelling that keeps you entertained the whole time - definitely book a tour with Colm on your next visit to Chicago! "
"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! "
"Mike ist ein unglaublich sympathischer Guide, der wirklich alles über Chicago weiß. Wir haben so viel gelernt über die Geschichte , die Architektur und wie diese großartige Stadt tickt.
Er hat es geschafft dass es ein spannender und lustiger 3 Stunden Walk war . Wir sind sehr froh ihn kennengelernt zu haben .😊"
