Great experience, will recommend to all of our friends. Great combination of favorite Chicago foods. Fran was an incredible guide!
About Activity
What's Included
Includes
- Tender Italian beef soaked in rich jus, warming you up like the perfect savory holiday comfort.
- A Chicago dog loaded with bold flavors—bright, zesty, and perfect for a festive winter bite.
- The original brownie—rich, warm, and fudgy, a sweet holiday treat that melts into pure joy.
- Enjoy deep dish pizza, Italian beef, a Chicago-style hot dog, brownies, hot apple cider, and festive bites that make this Chicago Food Tour a Holidays and Christmas feast of iconic city flavors.
- Hot Christkindlmarket cider—steaming, spiced, and soul-warming, the perfect festive winter sip.
- Savor Chicago-style pizza, a warm Christmas and Holidays favorite baked to perfection.
- Led by a local English-speaking guide
Excludes
- $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
- Hotel pickup and drop-off
- Local drink samples can be added for a fee (Three 9oz pours)
Departure & Return
Departure Point
- Departure Point: Plaza of the Americas - Northside of Wrigley Building - Michigan Avenue ground level (next to the BIG ANGEL WINGS). Directions: For your Chicago Food Tour, your Guide will be wearing a Bobby's Bike Hike shirt with branded paddle. Then you will begin your Food tour in Chicago.
Return
- This is where your Seasonal Chicago Food Tour will end. Chicago’s Christkindlmarket wraps you in a glowing European village of twinkling lights, handcrafted treasures, and irresistible holiday treats—an unforgettable winter tradition and the perfect ending to an incredible food tour in Chicago.
Itinerary
Skip the lines, VIP style, at Chicago’s iconic Christkindlmarket. This Chicago Food Tour stop for hot cider becomes pure festive magic—steaming mugs of spiced apple warmth, German holiday stalls glowing with twinkling lights, and the cozy scent of cinnamon drifting through the air. As you sip this handcrafted treat, you’re wrapped in the joy of Chicago Christmas, surrounded by artisans, music, and the nostalgic charm of a European winter village. This unforgettable taste of Chicago Holidays captures the season in a cup and invites every food lover to savor the city’s most heart-warming tradition.
Your Chicago Food Tour treats guests to a true Chicago Christmas indulgence with a stop at one of the city’s legendary deep-dish institutions—Lou Malnati’s, Giordano’s, or Pizzeria Uno—each offering its own mouth-watering take on the iconic pie. The aroma alone pulls you in: buttery, golden crust; layers of bubbling cheese; rich, zesty tomato sauce; and toppings that melt right into the slice. Food lovers adore learning that deep dish wasn’t created as a tourist novelty—it was invented right here in 1943 at Pizzeria Uno as a hearty, sit-down meal for Chicago’s working crowd, a recipe that sparked a citywide tradition still fiercely beloved today. During the Chicago Holidays, savoring this warm, comforting classic feels like the culinary version of stepping inside from the cold. It’s the kind of festive bite that makes guests rave and reminds them why Chicago is one of the world’s great pizza capitals.
The Chicago City Christmas Tree rises as the shimmering centerpiece of the Chicago Holidays, and your Chicago Food Tour brings you right into its glow. Dressed in thousands of sparkling lights and vibrant ornaments, this massive evergreen transforms Millennium Park into a true Chicago Christmas wonderland. What many visitors don’t realize is that the tree isn’t commercially purchased—each year, a family from the Chicagoland area donates a beloved spruce or fir from their own property, and the city carefully inspects dozens of submissions before selecting the perfect one. This long-standing tradition gives the tree a personal, hometown story every season, making it a symbol of community as much as holiday magic. It’s a spectacular stop that captures everything warm, bright, and joyful about winter in Chicago.
The Millennium Park ice skating rink brings pure seasonal joy to your Chicago Food Tour, capturing everything magical about the Chicago Holidays and Chicago Christmas. As skaters glide beneath the towering skyline, the scene feels straight out of a winter postcard—twinkling lights, music drifting through the park, and crowds cheering on family and friends. The rink is extra special because it was designed as a public, free-to-access winter attraction from day one, intentionally placed along Michigan Avenue so visitors could watch the skaters from the street and feel invited to join the fun. Its long, ribbon-like shape also gives skaters more room to move than a traditional oval rink, making the experience feel open and effortless. Whether you skate or simply take in the festive energy, this stop delivers one of the city’s most joyful holiday moments.
Michigan Avenue glows with holiday magic during the Chicago Holidays, and your Chicago Food Tour brings guests right into the heart of the season along one of the world’s most famous shopping avenues. The trees lining the Magnificent Mile sparkle with thousands of white lights, transforming the street into a glittering Chicago Christmas promenade. What makes this display even more enchanting is its festive kickoff: every year, the Magnificent Mile Lights Festival launches the holiday shopping season with a massive celebration featuring live music, a parade led by Mickey and Minnie Mouse, and the moment when more than a million lights switch on at once, illuminating the entire avenue. The tradition dates back to the early 1990s and has become one of Chicago’s most cherished seasonal events. Strolling this radiant stretch, guests feel the excitement, nostalgia, and wonder that make Chicago’s holiday season unforgettable.
The Wrigley Building becomes a dazzling beacon during the Chicago Holidays, and your Chicago Food Tour stop here brings guests right into its warm seasonal glow. Its white terracotta façade lights up beautifully against the winter sky, making it one of the most photogenic spots of Chicago Christmas. Holiday wreaths, garlands, and the building’s signature two-tower design create a timeless backdrop for the season. Many visitors are surprised to learn that this was the first major skyscraper north of the river, built to resemble a Spanish cathedral tower so it would shine brightly as a welcoming gateway into the city. Its clock tower was intentionally illuminated to guide travelers arriving after dark—an early nod to Chicago’s reputation for hospitality. Standing beneath its holiday décor, guests feel the charm of old Chicago wrapped in festive cheer, making this stop a favorite for culture lovers and architecture fans alike.
Inside the elegant Palmer House Hotel, your Chicago Food Tour steps into holiday luxury with the world-famous original brownie—rich, chocolatey, and still baked from the 1893 recipe that started it all. The moment you taste its warm, fudgy decadence, you’re wrapped in the glow of Chicago Christmas, surrounded by sparkling décor and timeless history that makes every bite feel like a festive celebration. This iconic stop blends culinary heritage with the magic of Chicago Holidays, creating a mouth-watering experience every food lover will want to savor.
The Jay Pritzker Pavilion adds a dramatic sweep to your Chicago Food Tour, offering a striking blend of art and architecture that feels made for the Chicago Holidays. Its flowing steel beams stretch across the sky like ribbons of silver, creating a one-of-a-kind winter stage. During Chicago Christmas, the pavilion feels alive—sound echoing softly through the trellis, lights glinting off the curves, and the entire park buzzing with seasonal excitement. It’s a moment that speaks to culture lovers, architecture fans, and holiday wanderers alike, inviting guests to experience Chicago’s creative spirit in full festive shine.
Your Chicago Food Tour brings the warmth of the season to life with a mouth-watering Italian beef sample—one of Chicago’s most beloved comfort foods, especially during the Chicago Holidays and Chicago Christmas season. Thin slices of slow-roasted beef are piled high on fresh bread, soaked in fragrant au jus, and topped with sweet peppers or spicy giardiniera that adds the perfect holiday kick. Guests love learning that this iconic sandwich was invented by South Side Italian immigrants in the 1930s, who sliced beef extra thin to stretch it for large family gatherings—turning necessity into one of Chicago’s greatest culinary traditions. The flavors are rich, juicy, and soul-warming, making this festive bite a highlight for food lovers eager to taste authentic Chicago history in every delicious mouthful.
Macy’s on State Street dazzles with its legendary holiday window displays, turning your Chicago Food Tour into a sparkling journey through nostalgia, artistry, and pure seasonal wonder. As whimsical scenes come alive behind the glass—twinkling lights, storybook characters, and vibrant winter worlds—you’re swept into the magic of Chicago Christmas, where tradition and creativity blend beautifully. This iconic moment of the Chicago Holidays invites culture lovers, families, and festive explorers alike to pause, soak in the cheer, and feel the city’s holiday spirit in its most enchanting form.
At Cloud Gate—Chicago’s beloved “Bean”—your Chicago Food Tour steps into a dreamy world of reflections and holiday sparkle that define the Chicago Holidays. As the polished steel curves mirror twinkling lights, downtown décor, and the joyful crowds of wintertime explorers, the sculpture becomes a breathtaking focal point of Chicago Christmas. Guests love discovering that Cloud Gate is made of 168 individually welded stainless-steel plates polished so flawlessly that the seams disappear, creating its iconic liquid-metal look. Standing beneath its arch, you can hear the soft echo created by its unique curvature—a design detail that surprises even longtime Chicagoans. It’s a stop that blends art, architecture, and holiday wonder, making it a highlight for visitors who want to experience Chicago’s creativity at its most magical.
The Art Institute’s iconic bronze lions make a memorable Chicago Food Tour stop during the Chicago Holidays, especially when they’re dressed in their festive Chicago Christmas wreaths. Standing proudly along Michigan Avenue, the guardians of the museum have been part of Chicago’s holiday season for more than a century, creating one of the city’s most beloved winter photo ops. Visitors are often surprised to learn that the lions don’t actually match—each was sculpted with a different pose and personality, described by the artist as one “on the prowl” and one “in an attitude of defiance.” Their seasonal wreathing tradition began in the early 1900s and has grown into a cherished city ritual. Surrounded by lights, music, and holiday energy, these majestic sculptures offer culture lovers a perfect blend of art, history, and festive Chicago spirit.
Millennium Park becomes a shimmering winter stage during the Chicago Holidays, and your Chicago Food Tour stop here lets guests soak in some of the season’s most iconic sights. From the bustling ice-skating rink framed by soaring skyline views to the city’s official Chicago Christmas tree glowing with ornaments and lights, the park radiates pure holiday joy. But here’s a fun fact most visitors never hear: Millennium Park isn’t actually built on solid ground—it sits atop an enormous rooftop, created above active railroad lines and parking structures. The entire landscape, from the lawns to the rink to the gardens, was engineered as a massive “living roof,” one of the largest of its kind in the world. It’s an incredible piece of design that makes this festive stop not only beautiful but a true Chicago innovation guests love learning about on the tour.
Your Chicago Food Tour wouldn’t be complete without a festive bite of the iconic Chicago-style hot dog, a perfect warm treat during the Chicago Holidays and Chicago Christmas season. This hometown classic arrives “dragged through the garden” on a steamed poppy-seed bun—snapping Vienna beef, bright yellow mustard, neon relish, crisp onions, juicy tomato wedges, a pickle spear, sport peppers, and a dash of celery salt. Food lovers are always surprised to learn that the Chicago dog was born during the Great Depression, when produce vendors near Maxwell Street piled inexpensive, flavorful toppings onto sausages to create a filling, affordable meal. That colorful lineup stuck, becoming a symbol of Chicago pride and a delicious reminder of the city’s resilience. Enjoying one on a chilly holiday night feels like tasting a piece of living Chicago history—comforting, vibrant, and absolutely unforgettable.
Daley Bicentennial Plaza offers a calm, snow-dusted retreat on your Chicago Food Tour, a gentle stretch of parkland where the Chicago Holidays feel bright and refreshing. Lined with softly lit trees and open winter pathways, the plaza gives guests a peaceful pause from the city’s bustle. During Chicago Christmas, the crisp air, twinkling décor, and skyline framing the park create a welcoming moment of seasonal beauty. And here’s a delightful fact many visitors never learn: this plaza was named in honor of Chicago’s bicentennial tribute to its earliest settlers, and it was intentionally designed as a “breathing space” to give Chicagoans a quiet refuge amid the growing downtown skyline. Its layout—broad lawns, long sightlines, and open promenades—was crafted to invite reflection, calm, and community gathering. It’s a rewarding stop for guests who love discovering hidden stories woven into Chicago’s holiday landscape.
State Street shines with classic holiday charm during the Chicago Holidays, and your Chicago Food Tour stop here immerses guests in the history and sparkle of one of Chicago’s most storied streets. Lined with glowing lights, festive storefronts, and the energy of winter crowds, State Street has long been a centerpiece of Chicago Christmas traditions. Many visitors don’t realize that this very street is home to Chicago’s annual Thanksgiving Day Parade, a tradition dating back to 1934 that was originally created to lift spirits during the Depression. That celebration now marks the unofficial start of the holiday season, and the festive lights that follow transform State Street into a warm, inviting holiday corridor. Walking here feels like stepping into a living timeline of Chicago’s winter traditions—full of color, history, and the excitement that makes the season come alive.
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Reviews
Surprisingly large amount of good but not amazing food (standard Chicago fare, not a foodie’s paradise), but it was our guide Fran that really made it special with her friendly “mom-like” demeanor and interesting stories about the points of interest along the way. The final stop Christkindlmart was absolutely mobbed despite Monday afternoon at 2:30 (on 12/22 tho); at least she had a skip-the-line entrance to get in. Overall we were very pleased we did it.
Need a good appetite and walking shoes. Very scenic never knew anything about underground center. Would highly recommend.
This is an absolute must of your in Chicago!! The amount of information, the good vibes, good food. Gabe, our tour guide, was very knowledgeable, great personality, very interactive, just all around good guy. I swear if we didn't do this, our trip would have been completely different.
Great tour! Had all the Chicago staples, Mickey was knowledgeable and a fun time. It was a frigid day, but the tour was still done well.
Really fun tour around the city! Kevin was a great tour guide. Was surprised to be dining with strangers but had a good group! Somewhat misleading that the tour isn’t of the market but rather ends there. All in all a great experience and fun time!
It was super cold but our guide was extremely friendly and made the weather bearable, he was funny and knowledgeable. The sites were awesome and the food delicious.
It was cold out..2 degrees, but tour full. Fran our tour guide, was fantastic. Food was delicious. Chicago history lesson and architectural lesson just as good. Would definitely recommend.
Our guide, Braedon was amazing. Very friendly and knowledgeable. Thoroughly enjoyed this tour and would do it again!!!
This was a very fun and educational tour. Braeden was our Guide and he was very pleasant and knowledgeable. You get to eat Chicago’s iconic dishes and learn about some of the city’s landmarks. Come hungry.
Fran was fantastic! Even though we were cold we still had an amazing time. Be sure to arrive hungry and enjoy the food and sights. A bonus is the expedited access to the Christmas market. We enjoyed pizza, chicago dog, Italian beef, the original brownie, popcorn and apple cider. This tour alone marked off all of the Christmas sights and food on our list. Thank you for making our trip memorable!
Very fun and festive. Dress warmly. Come with an empty stomach to enjoy all the Chicago foods on this tour.
You will get lots of delicious food to eat. You will walk a lot. You will learn a lot about the history of several of the buildings in Chicago. You will have a great time.
Really fun and engaging. Meet some very nice people and enjoyed the time we had. Lots on new things that you would normally walk by were pointed out.
We learned so much about the rich history of Chicago, the people who started the restaurants, the history of Chicago’s iconic foods: pizza, hot dogs, Italian beef sandwiches, this fires that destroyed Chicago and how the Chicago people rebuilt it time and time again. If you like good food, entertaining/educational presentations, this is definitely your kind of day trip! As I said our guide was Jeff who is a gifted storyteller with an endless vault of Chicago history. Ask for Jeff when you book your food adventure. He is an A+ guide.
If you're here in the city during the winter (especially if it's your first time), this is a great way to stay your trip! See all the biggest sights and taste the signature tastes. Is your starting longer than the day, this is great way to get your bearings off the city before deciding where and what you want to do
Today I found out it was a FBA woman named Alice Mae Redmond who created the deep dish pizza in Chicago! She gets no recognition for it in Chicago but that’s nothing new. Enjoy!
I had an amazing time on this tour! Jamal was my tour guide. He was so nice and had great information about the restaurants and the city. I tried a lot of food I wouldn't have gotten on my own, and was able to see a lot of the city in only 3 hours. My only suggestion would be for the tour to arrange our apple cider in a souvenir mug!
We had Mickey as our guide and he was absolutely amazing!!! Super informative, friendly and funny! He did an amazing job and took us to some really cool spots.
Hi, I had Lilian for our group leader. I know I didn’t spell her name right but she was wonderful. I loved hearing about the history and everything of Chicago. I have been to Chicago in 2008 but had not taken this tour before obviously cause this was a holiday hike got to see like Christmas stuff and everything. The only thing I wish is that I thought we were gonna go inside the Palmer house so I’m gonna make an effort to go by today. I haven’t tried my brownie yet, but I wanna go in there and just look around because of the history other than that everything else was wonderful on the trip
We loved our tour!!! Learned so much about the city and got to eat some delicious food!! Would definitely recommend doing!! Lillian was our tour guide. She was great!!
Best pizza I ever had in my life—78 yrs old. Guide had fun w us, gave us lots of info & let us contribute info. The group was very open, young, energetic. We got along so well—several international visitors. Two others I was traveling w didn’t go and after hearing of my tour experience, were wishing they had gone. Don’t miss it, especially if you like to eat—they have the food ready when you arrive!
Jeanine wea a great guide! Lots of good food from deep dish pizza, beef sandwich, Garrett’s popcorn, Chicago dog, and the Palmer brownie. Every stop was well organize, and we stayed on track for the 3 hour time limit. Our guide was very entertaining.
Even though it was 28°, we had a blast on this tour. Our guide, Jeff was informative, entertaining, and enthusiastic! Plenty to eat too, complete with snacks. Would highly recommend!
Our guide, Mickey, was awesome. The food samples were a great way to experience some of Chicago’s best dishes in one trip.
Our tour guide Mickey was high energy and enthusiastic. His jokes and intros brought us together as a group and he kept track of us along all of our stops so no one got lost. He kept us on track and was full of facts about each stop. They also gave us an amazing amount of delicious food and I was stuffed. Highly recommend. I’m a local living in Chicago and learned and saw many new things along the way!
Such a fun tour. Julia was AMAZING and so knowledgeable. A great way to sample Chicago’s most popular culinary delights while learning about the city and its history. A must do tour!!
Great tour. The food and drink were delicious and Our tour guide Mickey was fun and knowledgable! Would recommend.
This was my husband and I first time visiting Chicago. I'm so happy I decided to do the tour and enjoyed every second of it. Our tour guide was Brooke, whom was very knowledgable of the entire city. I would definitely recommend this tour when visiting Chicago and ask for Brooke, she was amazing.
We enjoyed the tour. It was great way to see and learn different things about the city. Fun trying true Chicago food. Mickey the tour guide was great!
Absolutely wonderful! Our your guide, Mickey Jordan, was fantastic. So knowledgeable and fun. The tour itself was great. Hit several Chicago landmarks along with sampling of great food.
Mickey was great! We really enjoyed his jokes and personal touch. He made the tour very comfortable and funny!
We really loved this tour. Brooke was knowledgeable with great energy. Loved her! One suggestion. During holidays when kriskrindlmarket cups are available, serve last stop hot chocolate in them for people taking tour.
This was mine and my husband's first time visiting Chicago together. I came to visit the Christkindlmarket, and I chose the Holiday Hike tour for its combination of food tastings and tour of the city. The food was full servings so quite filling after visiting three restaurants. We visited some key points of interest along the way, and our tour guide, Mickey, did a great job of educating us on the history of each location/meal we tried. There were 12 of us in our party, and Mickey helped to break the ice amongst the group. My only "disappointment" was thinking the samples would be from the Christkindlmarket since it said "seasonal samples" and had the photo of the market. Did get a Belgian Chocolate at the market, but would have loved a brat or pretzel. Still would highly recommend. Worth the investment.
We loved our guide Greg. He had great stories that I had not heard before even though I have visited Chicago several times.
Super fun guide Hannah, great organization and stops! We had a blast! Nice to get express access to the Christmas Market.
We had a great time with our host Mickie, and the food portions were more substantial and delicious than we expected. We learned a lot about history and traditions of Chicago.
Julia was great. Made the walking tour so fun. Food was great Got into the Market so fast and easy!!
A lot of fun, even if you have lived in Chicago all your life. Brooke was a great guide. Knowledgeable, funny, dramatic in historical information, concerned for our safety. Particularly at the holiday time of the year. Look forward for doing this again with other family members and friends.
Loved the option to have a beer tasting from the local brewery and our tour guide was awesome. The food was delicious and the pizza from Lou Malnati’s pizzeria was the best deep dish we’ve ever had.
This tour was wonderful and I would highly recommend it to anyone. Our tour guide, Julia, did an excellent job of telling us about Chicago’s history and taking us to the most popular spots in Chicago. One of my favorite things about the tour was being able to walk into restaurants and not have to wait to be seated or for our food and drinks. It was a very busy day in Chicago so this made it easy to see a lot more than doing it on your own.
A fun and informative way to experience Chicago’s famous non-foodie foods with a jovial and quick witted guide. Josie entertained us and expedited our feasting at several local establishments on a very busy December Saturday. As others may have already mentioned… do not eat much, if anything prior to this tour. We were served nearly full portions at each of the stops. Josie reeled off fun Chicago facts and kept us entertained as we made our way from one food stop to the next. Her upbeat vibe made the tour a hit for us.
We had a great time. Josey was an amazing guide. We would recommend to anybody visiting the city of Chicago.
Josie is a wonderful guide. She is funny, knowledgeable, and quite informative. She organized our time well and kept us moving.
It was a great experience! Josie did an excellent job leading us through the city and giving us all kinds of facts with a touch of humor. Would highly recommend this food tour!
This is a must do tour whilst in Chicago! Josie our guide was so knowledgeable and made the tour fun for everyone. The food stops were amazing and Josie was able to answer all our questions without any hesitation. This walking tour gives you a great insight to what Chicago offers. If you do just one tour do this one and upgrade to include the beers - you won’t regret it. Oh and also don’t eat too much before this walking tour as food portions are good sizes
We had a fabulous time with Josie guiding us through some historical, beautiful and delicious sites in downtown Chicago. We came to appreciate some of the amazing history of the city and enjoyed some delicious and iconic flavors that Chicago is known for along the way. It was a fantastic activity to enjoy with family and I new friends met during the tour. Thank you Josie!
Learning the history around the food of Chicago was my favorite part. Tour guide Josie was knowledgeable and personable.
Josie was fabulous; even had some well times dad jokes 🤣 Was pleasantly surprised by the food portions and great beer selection. Loved the history and stories.
The food was of much larger portions then thought they would be giving an much better experience. Our guide was knowledgeable and very nice
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