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Northwest Side Neighborhood Holiday Bar Crawl

Celebrate the holiday in historic bars

Do something different to celebrate the holidays in Chicago on an action-packed holiday bar crawl with dinner! This holiday bar crawl with visual scavenger hunt will get you out of the hubbub of downtown and into the winter wonderland of Chicago neighborhoods, where the tinsel sparkles like a cool pour of Old Style. Designed for groups of 16-34 guests, this holiday bar crawl adventure takes your group to two dive bars and a homey ’70s joint for pizza and beer. Swedish spiced wine (glogg) is your dessert.

While on the bus, your guide will share some basic background on the Chicago neighborhoods of Avondale, Irving Park, and Albany Park as well as the stories behind each locale on your holiday bar crawl. This tour is especially designed for family groups and corporate groups who reside in Chicago. The tour guide commentary will be more minimal than our other private group tours, giving you and your company team or other special guests a chance to both compete in a visual scavenger hunt and also have time to connect with each other in fun, historic settings. The game is designed to inspire careful observation of these unique environs as well as some playful competition. Part of it is a contest for the most ridiculous selfie with your tour guide as the judge. Prizes will be awarded!

We have tested and scoped out an excellent mix of stops. Your group will visit an 80-year-old dive bar, a historic pizza institution, and a neighborhood bar totally decked out with holiday decorations. By getting out of impersonal downtown, your team will be surrounded with the welcoming vibes of neighborhood bar regulars. The kitschy, quirky and vintage decor of each locale makes them particularly worthy of a photo shoot. Your holiday bar crawl ends in West Avondale, where guests can choose to either get a nightcap at another bar within walking distance or Uber home.

All-inclusive group holiday bar crawl rate is $70 per person with a minimum of 16 guests. This price includes party organizer, coach transport, prizes, all food and drink, restaurant taxes, amusement tax and guide gratuity. This is an excellent value compared to other holiday party packages, especially those that do not include tax and gratuities.


  • Easy party planning!  We will be your one-stop party shop to organize your holiday party. You just need to send your holiday party invites and we prepare everything else.
  • Unique group experience!  Everyone has been to dinner or drinks but have they been to these neighborhood institutions, and via a bus?!
  • Action-packed!  All our stops are quick and unique, making for a condensed and exciting party.
  • Controlled drinking!  There’s often that one person who lets it loose a little much. The pace of this bar crawl stymies overindulgence with three drinks over two hours. This isn’t some TBOX holiday bar crawl!
  • During your party, you get to enjoy yourself! Leave all the details to us so that you – the party planner – can relax and have fun on the day of your holiday party.


The duration of the Northside Neighborhoods Holiday Bar Crawl for 16-21 guests is 2 hours and you have use of the bus for up to 3 hours.

With a larger group of 22-34 guests, we allot 2.5 hours.


2-2.5 hours


Minimal walking


  • Explore Chicago neighborhoods
  • Eat delicious pizza in a time-warped institution
  • Indulge in home-made Mexican hot chocolate
  • Play a holiday selfie contest and win prizes
  • Feel cozy among vintage holiday decorations
  • Make memories with your corporate or family group

Stories & Ideas

  • Unique stories behind two bars and a pizza joint/liquor store
  • Background on Irving Park and Avondale neighborhoods
  • History of drinking in Chicago bars
  • Inside scoop on eccentric bar characters

Tour Includes

Tour Location

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Call: 312.350.1131
E-Mail: [email protected]