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Duration: 5 hours

Overview

Spend five hours walking 2.5 miles through downtown Chicago, Illinois, sampling five classic dishes from deep dish pizza to Garrett popcorn along the way.

🥨 Sample five Chicago classics: deep dish pizza, Italian beef, a hot dog, Garrett Popcorn, and a delicious brownie

🏙️ Visit the Historic Water Tower, Millennium Park, the Chicago Riverwalk, and State Street

🫘 See Cloud Gate, the Crown Fountain, and the Pritzker Pavilion up close

🚲 Redeem a free two-hour bike or kayak rental within three days of the tour

This is Bobby's Bike Hike's most complete day out: a five hour walking tour that pairs Chicago's most famous foods with its most photographed landmarks. Guests start at the Historic Water Tower, one of the few buildings to survive the Great Chicago Fire, before working through deep dish pizza, an Italian beef sandwich, a Chicago-style hot dog, Garrett Popcorn, and an original recipe brownie across five stops.

Between bites, the route covers Michigan Avenue, the Chicago Riverwalk, the Chicago Theatre, Millennium Park, and Daley Plaza, with a guide sharing the history behind each stop. Every ticket includes a free two-hour bike or kayak rental to redeem within three day.

This is Bobby's Bike Hike's most complete day out: a five hour walking tour that pairs Chicago's most famous foods with its most photographed landmarks. Guests start at the Historic Water Tower, one of the few buildings to survive the Great Chicago Fire, before working through deep dish pizza, an Italian beef sandwich, a Chicago-style hot dog, Garrett Popcorn, and an original recipe brownie across five stops.

Between bites, the route covers Michigan Avenue, the Chicago Riverwalk, the Chicago Theatre, Millennium Park, and Daley Plaza, with a guide sharing the history behind each stop. Every ticket includes a free two-hour bike or kayak rental to redeem within three day.

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.

Year-Round,
Saturdays 10:30am

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.

Year-Round,
Saturdays 10:30am

Any restrictions to participate?

  • Ages: All ages are welcome.
  • Experience level: All levels are welcome, rated an easy stroll.

Who can you accommodate for?

  • Dietary restrictions: Vegetarian options are available; additional costs may apply for restricted diets or menu changes.
  • Pets: Sorry, no pets allowed.

What to expect on the day of the experience?

  • Duration: 5 hours.
  • What's included:
    • Tour prices include all five food samples.
    • Storied history of Chicago’s classic dishes and the establishments that created them.
    • Informative walking tour of the Windy City’s most beloved landmarks.
    • Either 2 hour bike rental or 2 hour kayak rental (to be used within three days of your tour, weather permitting.)
      • *excludes Saturdays between Memorial Day Weekend to Labor Day. Kayaking only available from June-September
  • Who will be present: A guide is present throughout, along with other participants (max 15 per guide).
  • Photo/video: Photos encouraged along the route.

How to prepare?

  • Weather dependency: Tours run snow, rain, or shine.
  • Arrival: Plan to arrive 15 minutes before the scheduled tour time.
  • What to wear: Comfortable clothing and shoes.
  • What to bring:
    • An ID
    • A bottle of water
  • Restrooms/lockers/changing rooms: Restrooms are available at the stops visited.

Any restrictions to participate?

  • Ages: All ages are welcome.
  • Experience level: All levels are welcome, rated an easy stroll.

Who can you accommodate for?

  • Dietary restrictions: Vegetarian options are available; additional costs may apply for restricted diets or menu changes.
  • Pets: Sorry, no pets allowed.

What to expect on the day of the experience?

  • Duration: 5 hours.
  • What's included:
    • Tour prices include all five food samples.
    • Storied history of Chicago’s classic dishes and the establishments that created them.
    • Informative walking tour of the Windy City’s most beloved landmarks.
    • Either 2 hour bike rental or 2 hour kayak rental (to be used within three days of your tour, weather permitting.)
      • *excludes Saturdays between Memorial Day Weekend to Labor Day. Kayaking only available from June-September
  • Who will be present: A guide is present throughout, along with other participants (max 15 per guide).
  • Photo/video: Photos encouraged along the route.

How to prepare?

  • Weather dependency: Tours run snow, rain, or shine.
  • Arrival: Plan to arrive 15 minutes before the scheduled tour time.
  • What to wear: Comfortable clothing and shoes.
  • What to bring:
    • An ID
    • A bottle of water
  • Restrooms/lockers/changing rooms: Restrooms are available at the stops visited.

Unused Experience Vouchers can be returned within 14 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 72 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 72 hours in advance means losing the value of your experience.

Unused Experience Vouchers can be returned within 14 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 72 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 72 hours in advance means losing the value of your experience.

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