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    5. Chicago Highlights Guided Running Tour
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    Chicago Highlights Guided Running Tour

    Run a curated route past Chicago’s top sights with history stops

    5.0 stars• 307 reviews
    From$51/ personincl. taxes and fees

    Duration

    1.5 Hour

    Highlights

    See Chicago’s popular attractions at a casual pace on a guided running tour. Stop along the way to hear stories about the “Second City” and take photos.

    • Explore Chicago highlights on a curated running route
    • Run at a casual pace with scheduled stops
    • Learn Chicago history with short talks along the way
    • Capture photos during planned breaks
    • Bring as little as possible while you run

    Things to know

    This is not a race, and you will make stops for history and photos.

    Cancellation Policy

    Full refund with 24 hours notice of cancellation. Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price and receive no refund.

    FAQs

    No. You run at a casual pace and stop along the way to talk about Chicago history and take photos.

    Bring as little as possible.

    Experience provided by Fit Tours NYC
    Experience provided by Fit Tours NYC

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

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    Person

    $51.94

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    307 reviews•Google Maps

    City Fit Tours has built a loyal following among travelers who want to combine sightseeing with exercise, and it's easy to see why. Guides like Lindsay, Holly, Tara, Jackie, and John consistently earn praise for being knowledgeable, friendly, and accommodating to different fitness levels. Most runners appreciate that the guides match their pace, pause for photos, and share interesting facts about NYC along the way. The company offers both group runs and personalized tours, with routes covering Central Park, the bridges, and neighborhood highlights. Even locals report discovering new spots and learning surprising history. That said, one reviewer had a disappointing experience where the guide didn't check in on the group's pace and seemed to lack route planning, making the tour feel rushed and disorganized. This appears to be an outlier though, as the vast majority of feedback highlights guides who are attentive and flexible. Many reviewers are repeat customers who book with them in multiple cities, which speaks volumes about consistency. It's a creative way to knock out your morning workout while actually seeing the sights, and several people mentioned it set a great tone for the rest of their day.

    What people are saying

    Review 1 of 5
    5/5

    I went on both the Central Park run with Lindsay and the Twin Bridges run with Holly. They were both SO MUCH FUN!! I highly recommend adding City Fit Tours to your itinerary--you won't be disappointed!!

    Photo of Christian Blome

    Christian Blome

    November 25, 2025

    Review 1 of 1
    5/5

    I went on both the Central Park run with Lindsay and the Twin Bridges run with Holly. They were both SO MUCH FUN!! I highly recommend adding City Fit Tours to your itinerary--you won't be disappointed!!

    Photo of Christian Blome

    Christian Blome

    November 25, 2025

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