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Duration: 1 hour


Lace up your running shoes and get ready for a blast with our Downtown Chicago 5k Fun Run – a unique way to explore the iconic sights of the city while staying active!

🏃‍♂️ Run your way through Chicago's most renowned landmarks, soaking in the city's vibrant atmosphere and iconic sights

🗺️ Our route is strategically planned to showcase the best of the city's attractions, making every step an exciting exploration

📚 Pause along the course to learn about the captivating history of the "Second City," adding an educational element to your run

🥇 Whether you're a seasoned runner or just out for a leisurely jog, our 5k Fun Run promises a memorable blend of exercise, entertainment, and camaraderie


When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Monday - Friday 7:00am
Saturdays 8:00am

Practical information

Any restrictions to participate?

  • Age: Not recommended for children under 16 years of age.
  • Physical limitations: There are a couple of legs of the 5K Fun Run that are just under .5 miles, so you need to be comfortable with this pace.

What to expect on the day of the experience?

  • Duration: 1 hour
  • What’s included: A guided 5k run through the city with stops to learn about the area.
  • Who will be present: You will have a guide with you at all times; also, other guests may be joining (up to 15 people).
  • Spectators: No spectators are allowed, everyone must have a ticket/reservations.
  • Photo/ video: You may take your own photos.

How to prepare?

  • Weather dependency: Rain or shine, the experience will be running. If conditions are not to your liking, you can reschedule to any of our partners other runs that have space available. In the event of dangerous weather (thunderstorms with lightning, extreme heat or cold, etc.) the partner will cancel the tour or look to reschedule.
  • Arrival: Plan to arrive 15 minutes in advance.
  • Parking: Parking can be challenging downtown, so please plan accordingly.
  • What to wear: Athletic clothing & good running shoes
  • What to bring: A water bottle

Full description

Our Downtown Chicago 5k Fun Run is the ultimate way to experience the city's top attractions while breaking a sweat. Join us on this exhilarating journey as we guide you through a thoughtfully designed course, giving you the chance to soak in the incredible energy of Chicago's bustling streets. Along the way, we'll make pit stops to uncover the intriguing history of the "Second City," adding an educational twist to your exercise. Whether you're a seasoned runner or just looking for a fun way to explore, this 5k run promises an unforgettable blend of activity, knowledge, and sheer enjoyment!

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 24 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 24 hours in advance means losing the value of your experience.

Duration: 1 hour
Regular price $51
$51 Regular price Sale price
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Here's what others have to say!



Based on 0 reviews

John G.

What an exhilarating way to see Chicago! The Downtown Chicago 5k Fun Run was a fantastic experience. Running through the iconic sights of the city while learning about its history was such a unique blend of activity and education. The guides were knowledgeable and kept the pace enjoyable for everyone. Whether you're a runner or just want to explore, this is a must-try!

Jane A.

I had a blast with the Downtown Chicago 5k Fun Run! It was a fun and casual way to experience the city's highlights. The guides were friendly and shared interesting historical tidbits that added a whole new layer to the run. The course was well-curated, and the pace was perfect for all levels of runners. Highly recommend it for both fitness enthusiasts and tourists!

Alex J.

Absolutely loved the Downtown Chicago 5k Fun Run! It's like a sightseeing tour with a fitness twist. Running through the city's top attractions while learning about its history made the experience unforgettable. The guides were engaging, the route was well-planned, and the pace was comfortable for everyone. Whether you're a local looking for a new adventure or a visitor wanting to see the city in a unique way, this run is a must-do!