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Evening Walking Tour

The Chicago Pizza & Cocktail Tour

Chicago's finest pizza paired with craft cocktails. A small-group evening walk through the city's best pizzerias and most interesting bars.

$89 / person

3 hours

By reservation

12 person max

3 pizza tastings

Craft cocktails included

Under 1.5 miles

Legendary Chicago pizza. Craft cocktails worth the walk between.

Our evening tour pairs three of Chicago's best pizzerias with the cocktails we'd actually order at each one. This is not a party crawl. It is a paced, guided walk with real pizza, real drinks, and real stories about the city in between. Perfect for date nights, visitors with a free evening, or private groups who want something different than another steakhouse dinner.

  • 3 full pizza tastings across different styles
  • A craft cocktail included at each stop
  • Small groups — 12 people maximum, keeping it intimate
  • Approximately 3 hours, covering under 1.5 miles on foot
  • 21+ required for the cocktail portion
  • Meet your guide at the first stop, listed on your ticket

A date night your out-of-town friends will still talk about next year.

Currently scheduled by request. Reach out and we'll make it happen. Inquire About a Date
Jonathan Porter, Founder of Chicago Pizza Tours
“Pizza and cocktails are what Chicagoans actually do on a great night out. This tour puts the two together the way they're meant to be — a real sit-down slice, a proper drink, and a guide who knows which bars still do it right. It's the tour I'd take my own friends on.”

Jonathan Porter

Founder, Chicago Pizza Tours

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Frequently Asked Questions

Yes. One craft cocktail at each of the three stops is included. Additional drinks are available for purchase, and non-alcoholic alternatives are offered for anyone who'd prefer them.

All pizza tastings and water are included. You'll try three different styles across the evening — plenty to eat as a full dinner.

21+ for the cocktail portion. Guests under 21 can join if we arrange a non-alcoholic package in advance — reach out and we'll work it out.

This tour runs by reservation, usually as a private or small-group booking. Send us a message with your preferred date and group size, and we'll get back to you with availability and next steps.

Absolutely — it's a great format for date nights, birthday groups, bachelor/bachelorette parties, and corporate outings. We can tailor the pizzerias and bars to your group. See our team outings page for details.

This is a walking tour, so we recommend dressing for the weather. Tours run rain or shine. We'll have umbrellas on hand if needed.

Yes — every restaurant and bar on the tour has restrooms.

Ready to Plan Your Night?

$89 per person. Booked by reservation for dates, groups, and private parties.

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