Chicago Highlights Running Tour – Explore the City on Foot
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Experience Chicago like never before with the Chicago Highlights Running Tour. This guided run takes you through the city's most famous sights, offering a unique way to explore the Windy City’s vibrant neighborhoods and iconic landmarks.
Starting from a central meeting point, you'll jog along the Lake Michigan shoreline, enjoying breathtaking views of the city skyline. The tour then winds through downtown Chicago and the Loop, crossing the Chicago River while sharing fascinating stories about the city’s colorful history—from notorious gangsters to marine disasters.
Next, you'll head up Michigan Avenue, passing cultural and architectural treasures like the Chicago Art Institute and historic buildings. Along the way, the guide will make stops to share insights and take photos, ensuring you capture memories without breaking your pace. This is a memorable experience perfect for runners and history enthusiasts alike.
While this isn't a race, it’s a fantastic way to see Chicago’s highlights at a relaxed pace, making it suitable for most adults with moderate fitness levels. Whether you're visiting for the first time or a local looking for a new perspective, this tour offers a fun, active way to discover the city.
Frequently asked questions
How long is the Chicago Highlights Running Tour?
The tour lasts approximately 1 hour and 15 minutes.
What languages are available for the tour?
The tour is offered in English and Spanish.
What is the group size?
Groups are limited to up to 10 participants.
Is this tour suitable for all ages?
It's recommended for adults aged 14 to 110 with at least a moderate level of physical fitness.
What is included in the tour?
A live, in-person running tour guide is included.
Can I cancel the tour if my plans change?
Yes, you can cancel for a full refund if done at least 24 hours before the scheduled start. Cancellations within 24 hours or due to bad weather may not be refunded.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 1 hour 15 min
Check availability to see start times.
Live tour guide
English, Spanish
Key facts
What's included
Included
- Live, in-person running tour guide
Itinerary
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Stop 1
Explore downtown Chicago's top attractions while running! The tour covers Grant and Millennium Parks, the Lakeshore, Navy Pier, Michigan Avenue, and the Chicago River. After the run, you'll feel like you've truly experienced the city's highlights.
Meeting point & pickup
Meet at the starting point
There is a plaza in front of the Apple Store entrance across from the Wrigley Building and the Tribune Tower. Your guide will be there.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day before
- 0% refund if cancelled within 0–1 day
- May be cancelled due to bad weather
Instant confirmation
Your booking is confirmed immediately after checkout.
From $44.00 per person
- Free cancellation
- Secure checkout with our booking partner
