Chicago Food Tour by Bike with Pizza, Beer, Hot Dogs, Cupcakes

Food, Wine & Nightlife in Chicago

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Tour description provided by Viator

Taste all of Chicago’s classic eats on this four-hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. The journey is 14 miles in total (traversed at a nice leisurely pace) and includes a slice of deep dish pizza, a gourmet cupcake, a Chicago-style hot dog, and a few samples of Chicago’s legendary craft beer! Between food and beverage stops, you’ll get to drink in the sights of Chicago’s beautiful north side neighborhoods, including the historic Wrigleyville district, home to our intrepid Chicago Cubs baseball team (and their fiercely loyal fans). Then you’ll get a chance to cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this rip-roaring good time! You’ll leave with a profound understanding of our town, even if you only came for the beer.
Our Bikes, Bites, & Brews Signature Edition tour combines the flavorful satisfaction of city food tours with the unadulterated fun of bicycling! Bypass the wait at some of the city’s most popular restaurants, and focus on enjoying amazing food and beer. The journey begins at our downtown headquarters, where our entertaining and enthusiastic guides will introduce you to our incredibly bike-friendly city streets. The tour then rolls through Streeterville, past the Magnificent Mile shopping district, and into the high-end Gold Coast neighborhood for some world-famous Chicago-style deep dish pizza. A Windy City tradition since 1943, deep dish pan pizza has been pleasing crowds for generations. Thick, buttery crust and loads of melted mozzarella are guaranteed. You’ll learn all about how this goliath pie is made and taste why it’s become a global phenomenon! The next leg of the adventure travels through leafy and sprawling Lincoln Park, playful Oz Park (a tribute to author L. Frank Baum), and into the historic Lincoln Park neighborhood for a gourmet cupcake. The cupcake craze is a national sensation, and Chicago bakeries do it best! Heading north, the tour enters Lakeview, a lively theatre and nightlife district. Here you’ll taste Chi Town’s paramount ketchup-free sandwich—The Chicago Style Hot Dog. Pure Vienna Beef, poppy seed buns, and all the fixings create a totally unique culinary experience. From Lakeview, it’s just a quick ride into the heart of Wrigleyville to Wrigley Field, home of the Chicago Cubs and their loyal fans. Here you’ll relax and enjoy a refreshing local craft beer, while basking in the glory of our 1908 and 2016 World Champions. You’ll catch a glimpse of the ivy-covered stadium, famous hand-operated scoreboard, and our one-of-a-kind rooftop bleachers. After Wrigley, the tour treks south along the beautiful Lakefront Trail. This wide bicycle and walking path lines Lake Michigan and will deliver you straight to one last beer stop—a refreshing local pour from one of Chicago countless craft breweries, served right on the water’s edge. On the final stretch of our trip, you’ll see how Chicago maintains our reputation as one of the country’s best (and most unexpected) beach towns. Sand, skyline, and clear blue water provide unmatched views for the end of our journey. The tour finishes back at the Bobby’s headquarters, after four hours and thirteen miles worth of fun.

What’s included

  • Bicycle
  • Helmet
  • Water Bottle
  • Expert local guide
  • Food and beer samples

What’s not included

  • Gratuity for guide (15-20% suggested, PayPal & Venmo available)


  • All necessary equipment included
  • All-inclusive tour
  • Cycle the city streets to absorb the local atmosphere
  • Fully narrated tour