Bucktown Pizza Crawl in Chicago

Chicago’s holiday season is nothing short of magical, with twinkling lights, bustling streets, and a warm, inviting atmosphere. The Bucktown Pizza Crawl offers a chance to savor some of the city’s best pizza while soaking up the festive sights. From deep-dish classics to New Haven-style slices, this tour blends culinary exploration with the seasonal charm that makes Chicago a winter wonderland.

We’re here to walk you through what makes this 2.5-hour guided experience so appealing—and why it might be just what your holiday itinerary needs. With a focus on authentic pizza joints, New York-style slices, and deep-dish favorites, plus stops at major holiday landmarks, this tour offers a tasty, visually rich encounter with Chicago during the most wonderful time of the year.

Three things we love about this tour: the knowledgeable guides who bring the city’s history alive, the chance to sample seriously good pizza in true Chicago style, and the festive holiday sights that make the city sparkle. One consideration? The tour is quite focused on Wicker Park and Bucktown, so if you’re looking for a broader city overview, you might want to combine it with other experiences.

This adventure is perfect for food lovers, holiday enthusiasts, or anyone seeking an authentic taste of Chicago’s local neighborhoods—all wrapped in a cheerful winter package.

Good To Know

• Authentic pizza experience: Sample a range of Chicago, New Haven, and NY-style slices.
• Local insights: Knowledgeable guides enhance the experience with tips and history.
• Festive sights: Enjoy Chicago’s holiday decorations, Macy’s, Daley Plaza, and Millennium Park.
• Neighborhood charm: Explore Bucktown and Wicker Park, vibrant communities with art and small businesses.
• Flexible and inclusive: Most travelers can participate, and it operates in all weather conditions.
• Value for price: The tour offers generous tastings, a local guide, and unique holiday views for $59 per person.

An In-Depth Look at the Chicago Pizza Crawl

Starting Point and General Overview

Kicking off at Piece Pizzeria and Brewery in Bucktown, the tour begins around 11:30 am. This neighborhood, once a hub for starving artists, has evolved into a lively family-oriented area that still preserves its artistic roots. As you start your walk, you’ll get a taste of Chicago’s rich culinary scene—focusing on pizza, but with a twist of neighborhood history and vibrant street life.

Why Bucktown & Wicker Park?

These districts are more than just pretty neighborhoods—they’re where Chicago’s modern art, small businesses, and diverse culture thrive. As your guide takes you past the Chicago 606 trail (a reimagined train line now used for biking and walking), you’ll learn that all Chicago zip codes start with 606—an interesting tidbit that adds local flavor to your walk.

Reviewers mention that the area has a genuine small-town feel, but with the energy of a big city. Maureen P, who enjoyed her holiday pizza tour, appreciated the guide’s knowledge and the chance to see Macy’s during her visit, which she found especially festive. She even added, “There was more than enough food and even more to take home,” highlighting the generous portions.

Stop 1: Piece Pizzeria and Brewery

This local favorite, established in 2001, is renowned for its East Coast-inspired pizza and Chicago craft brews. You’ll sample a full slice of Chicago-style deep-dish along with New Haven-style pizza and NY street slices—giving you a comprehensive taste of the city’s diverse pizza styles.

Guests often praise the staff for their friendly service and the quality of the pizza. One reviewer mentioned that “the guide was very knowledgeable and answered all our questions,” making it a more enriching experience. The 45-minute stop offers plenty of time to indulge and chat.

Stop 2: Paulie Gee’s Wicker Park

Hailing from Brooklyn, Paulie Gee’s is a well-known national brand that found a home in Chicago’s Wicker Park. Its first Chicago location in Logan Square quickly gained popularity, and the Wicker Park spot continues that tradition with creative toppings and a cozy vibe.

As we walk past boutique shops and street murals, your guide shares insights about the neighborhood’s artistic history. The pizza here tends to be more inventive, with a focus on quality ingredients. Reviewers note that “the pizza is delicious, and the guide’s stories about the neighborhood made it even better.”

Stop 3: My Pi Pizza

This unassuming spot on Damen Avenue is revered locally for its deep-dish slices that stand out from the big-name chains. Owner Rich carries on his father’s tradition, and many say this is one of Chicago’s best-kept secrets for authentic deep-dish.

This 45-minute stop is a favorite for those craving a hearty, cheesy slice. Reviewers appreciate the warm, family-run vibe and mention that “the owner’s passion really shows in the pizza.” It’s a perfect conclusion for a food-focused tour.

Walking through Wicker Park and Bucktown

Wicker Park has become a hub for boutique shopping, street art, and small businesses, making it a lively backdrop for your pizza tastings. The tour guides usually point out local landmarks and hidden gems, giving you a sense of the area’s creative spirit. As one reviewer put it, “The neighborhood’s charm really comes alive during the tour, especially while walking past the 606 trail.”

Holiday Sights & Festive Moments

As you finish your pizza tour, you’ll walk past iconic holiday spots like Daley Plaza’s Christmas tree, the Millennium Park skating rink, and the Cultural Center. These sights bring the season’s spirit alive, especially with the beautiful lights and decorations.

Guests have especially enjoyed seeing Macy’s decorated windows and hearing stories about the famous Marshall Field Building. The tour ends around 2 pm at My Pi Pizza, about half a mile from the start point, giving you ample time to explore further or step into the local shops.

The Value of the Experience

At $59 per person, this tour offers a lot of value—especially considering the generous pizza portions, the guided insights, and the holiday ambiance. The all-weather operation means you’re covered regardless of the forecast, and the small group size (max 16 travelers) ensures a more intimate experience.

Most reviewers highlight the knowledge and friendliness of the guides as a key highlight. Maureen P’s review mentions that “the guide was very knowledgeable and answered all our questions,” which added a layer of depth to their enjoyment.

While not including alcoholic beverages, the tour gives you the opportunity to purchase local brews, and the included hot chocolate from Magnolia Bakery provides a cozy, sweet finish to your walk.

Practical Tips for Travelers

• Book in advance: The tour is popular, often booked 75 days ahead.
• Dress appropriately: Operates in all weather, so layers and rain gear are advisable.
• Bring cash or card: For additional purchases or tips.
• Arrive on time: The tour starts promptly at 11:30 am.
• Enjoy at your own pace: There’s plenty of time to savor each slice and take photos.

Who Should Consider This Tour?

This pizza crawl is ideal for food lovers eager to taste Chicago’s pizza, especially if you want to explore local neighborhoods beyond downtown. It’s also a good choice for those interested in combining culinary treats with holiday sights. Families, couples, or groups of friends — especially those who enjoy walking and small-group experiences — will find this tour engaging and fun.

If your goal is a relaxed, flavorful morning with plenty of sightseeing sprinkled in, this tour hits the sweet spot. It’s particularly well-suited for travelers who appreciate a local guide’s insights and are happy to indulge in generous slices of Chicago’s best pizza.

Final Verdict

The Bucktown Pizza Crawl delivers exactly what it promises: an authentic, fun, and festive way to experience Chicago’s neighborhoods during the holiday season. With knowledgeable guides, hearty tastings, and charming sights, it’s a dependable choice for anyone wanting a flavor-packed, city-centered experience.

If you’re a pizza enthusiast or a holiday lover looking to combine food with sightseeing, this tour is worth considering. The small group size, inclusive atmosphere, and focus on local gems all add up to a memorable day in Chicago.

FAQs

Is there an age limit for this tour?
Most travelers can participate, and the tour is suitable for a wide age range. Children and teens who enjoy pizza and walking will also have a good time.

How long is the tour?
The tour lasts approximately 2 hours and 30 minutes, including stops at three pizza joints and some walking around the neighborhoods.

Where does the tour start and end?
It begins at Piece Pizzeria and Brewery on North Avenue and ends about half a mile away at My Pi Pizza on Damen Avenue.

Do I need to book in advance?
Yes, as the tour is popular and often booked 75 days in advance. Booking early ensures a spot.

What is included in the price?
You get slices of New Haven, NY-style, and deep-dish pizza, water, and a knowledgeable guide. Hot chocolate is also included at the end.

Are alcoholic beverages available?
They are not included but can be purchased separately at the stops.

What should I wear?
Dress for the weather—layers are best, and an umbrella or raincoat if needed, since it operates in all weather conditions.

Can I customize dietary requirements?
It’s best to advise at booking if you have specific dietary needs, though most pizza options are typical and carb-heavy.

Is tipping the guide necessary?
While not obligatory, tipping is appreciated and generally recommended for good service.

Embark on this flavorful holiday walk through Chicago’s vibrant neighborhoods, and enjoy the perfect blend of festivity, local flavor, and warm community spirit.