Experience Half-day tours in the best of Chicago with Withlocals
On a Half day visit in Chicago? Chicago is a treasure chest full of cultural gems! From galleries & museums insights to street art walks, cultural events and more. Uncover the authentic side of Chicago on an arts & culture private experiences with the local expert of your choice.
On a Half day visit in Chicago? Chicago is a treasure chest full of cultural gems! From galleries & museums insights to street art walks, cultural events and more. Uncover the authentic side of Chicago on an arts & culture private experiences with the local expert of your choice.
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.
Top 3 half-day tours in Chicago
Make your stay in Chicago complete with these things to do
1
Choose your favorite local
Highlights & Hidden Gems of Chicago
18 reviews
3 hours | City highlights 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!
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.
Step Back in Time: A Tour of Pullman's Company Town
5 reviews
4 hours | City highlights 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!
"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 .😊"
