Bucktown Pizza Crawl in Chicago

If you’re visiting Chicago during the holiday season, a tour that combines festive sights with gourmet pizza sounds like a perfect way to soak in the city’s charm. The Bucktown Pizza Crawl offers just that—a flavorful journey through some of Chicago’s best pizza joints, sprinkled with the sparkle of Christmas lights and cozy holiday vibes. With a well-reviewed 5-star rating and a carefully curated itinerary, this experience promises a mix of culture, cuisine, and community spirit.

What we really love about this tour is its focus on authentic local flavors—sampling real Chicago deep-dish and New Haven-style pizza—while wandering through vibrant neighborhoods that have kept their artistic soul intact. The tour’s guides are praised for their knowledge and friendliness, making it more than just a food tasting; it’s a cultural walk with delicious rewards. One potential drawback is the 2.5-hour walking component, which may be a bit tiring for those with mobility issues or those who prefer more structured, seated experiences.

This pizza crawl is best suited for travelers who enjoy walking tours, are curious about Chicago’s neighborhoods, and love trying different pizza styles. It’s especially appealing during winter, as it combines outdoor exploration with hearty food and holiday cheer.

• Authentic Chicago and New Haven-style pizza: Sample slices from renowned local pizzerias.
• Vibrant neighborhoods: Discover Bucktown and Wicker Park’s artistic and lively atmospheres.
• Festive sights: See iconic holiday landmarks like Daley Plaza, Millennium Park, and Macy’s decorated for Christmas.
• Knowledgeable guides: Experts who share interesting tidbits about Chicago’s history and holiday traditions.
• Balanced experience: 2.5 hours of walking with ample food, making it a manageable yet fulfilling tour.
• Value for money: For $59, you get multiple pizza tastings, a guided walk, and a festive atmosphere—well worth it for food lovers and holiday enthusiasts.

Starting Point and Overall Experience

The tour begins at Piece Pizzeria and Brewery in Bucktown at 11:30 am, a lively spot established in 2001. Here, you get your first taste of New Haven-style pizza, famous for its thin, crispy crust and flavorful toppings. Your guide, who’s often praised for their knowledge and friendliness, will kick off the experience with a brief overview of the neighborhood’s transformation from an artist’s haven to a family-friendly hub filled with boutiques and small businesses.

Walking through Bucktown, you’ll pass Chicago’s 606—a scenic, reimagined elevated trail that was once a train line. Here, the tour’s pace is leisurely but engaging, perfect for taking in the sights and chatting with fellow travelers. You’ll learn that all Chicago zip codes start with 606, a fun fact that adds local flavor to the walk.

Pizza Stops: A Tasting Tour for Your Taste Buds

Stop 1: Piece Pizzeria and Brewery (45 minutes)

This spot sets the tone with East Coast pizza expertise combined with Chicago craft brews. The New Haven-style slices here are prized for their thinness and crispiness, a nice contrast to the Chicago deep-dish that follows later. You’ll likely enjoy more than just the pizza—perhaps some details about how the brewery pairs its beers with slices.

Stop 2: Paulie Gee’s Wicker Park (45 minutes)

Next, the tour moves to Paulie Gee’s, a Brooklyn-born brand that’s become a nationwide favorite. Their Wicker Park location exemplifies the artisan pizza scene, with a reputation for innovative toppings and a cozy atmosphere. The guide might share stories of how Paulie Gee’s expanded from Brooklyn to Chicago, highlighting the city’s growing pizza culture. Reviewers mention the guide’s ability to answer questions with ease, making the experience both informative and fun.

Stop 3: My Pi Pizza (45 minutes)

The final stop is My Pi Pizza on Damen Ave, a family-run spot that continues a tradition started by the owner’s father. This place shines with Chicago deep-dish slices—thick, hearty, and loaded with cheese and toppings. Unlike the big-name pizzerias, this spot is praised for its authenticity and quality. Guests note that it’s a “no-frills” place, but the pizza is among Chicago’s best.

Sights and Holiday Festivities Along the Way

Beyond pizza, the tour includes visits to Daley Plaza, where the iconic Christmas tree illuminates the city’s skyline. You’ll also see Millennium Park’s skating rink, the Cultural Center, and the underground Pedway—each adding layers of holiday magic and local culture.

The Macy’s department store inside the Marshall Field Building is a highlight, with its decorated windows and historic ambiance. Guests have appreciated the fact that the tour includes a stop at Macy’s because it’s a beloved holiday tradition for many Chicagoans, plus it offers a great photo op. You’ll finish the tour with hot chocolate from Magnolia Bakery and sweet treats like Frango mint pie and mini cannoli, which provide a perfect warm-up after walking.

Practical Details and Value

At $59 per person, the tour offers excellent value—you get multiple full slices of pizza, a guided walk through lively neighborhoods, and a taste of Chicago’s holiday spirit. The small group size (max 16 travelers) makes for a more intimate experience, where guides can share personal insights and answer questions thoroughly.

While parking and hotel pickup aren’t included, the starting location is near public transportation, making it accessible for most travelers. The tour operates in all weather conditions, so dress accordingly for winter chills or snow.

Authenticity and Reviewed Experiences

One guest, Maureen P, remarked, “We really enjoyed our holiday pizza tour. The guide was very knowledgeable and answered all our questions.” She also appreciated the generous food portions, noting she had plenty to take home. This suggests the tour is well-paced and generous with tastings, making it a satisfying experience rather than a quick snack.

Another reviewer praised the guide’s ability to share Chicago’s holiday history, especially around Macy’s and the tree, enriching the experience beyond just pizza.

Final Thoughts: Is It Worth It?

This tour strikes a good balance between culinary delight, local culture, and seasonal festivities. It’s best suited for food lovers, holiday enthusiasts, and those interested in Chicago’s neighborhoods. The small-group format and knowledgeable guides ensure you won’t just walk and eat, but also learn and enjoy in a relaxed, friendly setting.

If you’re in Chicago during December and want a fun, flavorful way to see the city’s holiday sights while indulging in some of the best pizza the city offers, this tour is a solid choice. Just dress warmly, bring your appetite, and prepare for a memorable, spirited walk through Chicago’s vibrant Bucktown and Wicker Park.

How long is the tour?
The tour lasts approximately 2 hours and 30 minutes, covering about a mile and a half of walking through Bucktown and Wicker Park.

What kinds of pizza are included?
You’ll sample New Haven-style slices, NY-style street slices, and a full Chicago deep-dish slice, giving you a taste of different regional styles.

Are the stops indoors or outdoors?
Most of the stops are at small restaurants and pizzerias, with some outdoor walking between locations, so dress for the weather.

Is the tour suitable for children?
Most travelers can participate, and it’s especially engaging for pizza lovers and those interested in Chicago neighborhoods. However, keep in mind the walking duration.

Are drinks included?
Hot chocolate from Magnolia Bakery is included, but alcoholic beverages are available for purchase at the stops.

Can I cancel the tour?
Yes, the tour offers free cancellation up to 24 hours in advance, allowing flexibility in case your plans change.

To sum it up, the Bucktown Pizza Crawl blends authentic pizza tasting with festive Chicago sights, making it an excellent choice for those wanting to experience the city’s culinary and holiday spirit in a relaxed, guided setting. The knowledgeable guides, generous tastings, and vibrant neighborhoods create an experience that goes beyond just eating—it’s about celebrating Chicago’s community, culture, and flavor. Perfect for a fun winter outing or a unique holiday tradition, this tour promises a memorable bite of Chicago’s best.