Exploring Chicago’s Culinary Delights: An Unforgettable Food Tour Across 30+ Eateries

Embark on a gastronomic adventure through the Windy City, where we sampled over 30 of Chicago’s most iconic and hidden culinary gems. Get ready to discover the ultimate food lover’s guide to this vibrant metropolis!

For us, travel isn’t just about seeing new sights; it’s a dedicated mission to uncover and savor the finest culinary offerings a city boasts. This passion drives our every trip, transforming each journey into an epicurean expedition. Long before we pack our bags, we immerse ourselves in meticulous research and planning, ensuring no exceptional dish or beloved eatery is overlooked. Our goal is always to maximize our time and, more importantly, our appetites, to embrace every incredible flavor a destination has to offer.

To navigate these delicious endeavors effectively, we adhere to a few guiding principles, though “try” is indeed the operative word! Sometimes, a dish is so extraordinarily good that our rules simply must be bent, if not outright broken. During the day, particularly when hopping between numerous establishments, we practice what we affectionately call the “2-bite rule.” This discipline allows us to sample a wide array of tantalizing treats—ordering everything that captivates our senses—without becoming overwhelmed or uncomfortably full. Of course, there are inevitable moments when two bites are simply insufficient, or when a flavor inspires us so deeply that we need more to truly understand it for future recreation at home. Beyond portion control, we also embrace the power of movement. In any walkable city, our unofficial “no taxi or transportation” policy ensures we’re actively exploring and, conveniently, walking off some of the delightful calories consumed. With these foundational rules in place, the city becomes our oyster, and we wholeheartedly dive into its culinary landscape.

Our most recent adventure took us to the heart of the Midwest: Chicago! This trip was a whirlwind of fun and flavor, yet despite our best efforts, we barely scratched the surface of the city’s vast gastronomic treasures. While we had visited Chicago several times before, this was our first dedicated tasting tour, executed in our signature style, and we were brimming with excitement. Over three days, we made an astounding 34 stops and traversed 25.1 miles on foot, all in pursuit of the most incredible food experiences Chicago generously presents.

Chicago’s Best Bakeries: A Sweet Seeker’s Paradise

As a passionate baker, exploring new bakeries is akin to visiting a museum for me—a source of profound inspiration and a wonderful way to support fellow talented artisans. My eyes light up the moment I step inside, surrounded by an array of tempting treats, each one begging to be sampled. And, more often than not, I endeavor to try them all! Our Chicago food tour featured numerous stops at the city’s incredible bakeries. Chicago truly overflows with these delightful establishments, and resisting the urge to visit as many as possible was simply not an option. Here’s a curated list of the bakeries we visited, what we savored, and what made each experience truly special…

• Sweet Mandy B’s – This charming bakery quickly became my absolute favorite, so much so that we returned for a second visit during our trip! Its inviting atmosphere and adorable decor instantly make you feel welcome, while its display cases overflow with an astonishing variety of incredible baked goods. On our second visit, we were greeted with complimentary mini cupcakes at the door, a gesture that truly made my heart swell with affection for this darling establishment. From perfectly soft cookies to elaborate cakes and everything in between, Sweet Mandy B’s excels in every category. While everything we tried was phenomenal, the chocolate-covered peanut butter chip brownie stood out as my ultimate favorite. I am already planning my return and can’t wait to recreate some of their marvelous creations in my own kitchen! (1208 W Webster Ave, Chicago IL 60614)

• Molly’s Cupcakes – Stepping into Molly’s Cupcakes felt like entering a dream, a wonderland of confectionery artistry! This place boasts some of the most innovative and imaginative cupcake flavors I’ve ever encountered. Each bite was an experience in itself, with incredible fillings that elevated the humble cupcake to an art form. I vividly remember one cupcake oozing with a rich peanut butter and chocolate ganache, while another surprised us with a generous stuffing of delicious cookie dough in its center. The flavors were truly out of this world, a testament to their scratch-made quality and the obvious passion infused into every single creation. Molly’s Cupcakes is a must-visit for any dessert enthusiast. (2536 N. Clark St., Chicago, IL 60614)

• The Twisted Baker – This small, cozy bakery exuded an undeniable charm that made us want to linger all day, sipping coffee and indulging our sweet cravings. The atmosphere was incredibly welcoming, a perfect spot for a relaxed treat. Among our selections, the chocolate-swirled peanut butter cheesecake was an absolute standout, earning its place as my favorite. The classic chocolate chip cookie was also fantastic, and the mini banana chocolate chip cupcake offered two bites of pure, unadulterated bliss. This little bakery truly captured our hearts with its delicious offerings and inviting ambiance. (1543 N Wells St, Chicago, IL 60610)

• Hendrixx Belgian Bakery – Hendrixx Belgian Bakery is a wonderfully stylish establishment, showcasing an array of beautifully crafted pastries and sweet treats that are almost too pretty to eat. It was immediately apparent that true culinary talent is at the heart of this bakery, with each item demonstrating exceptional skill. The Belgian waffle was a particular highlight: sweet and delightfully crispy on the outside, yielding to a satisfyingly chewy interior. It tasted like a sophisticated cookie in waffle form, and I adored it! The pistachio macaroon was a masterpiece of flavor and texture, almost too lovely to disturb. While the chocolate almond croissant was certainly tasty, my inner chocoholic wished for a slightly more generous chocolate filling—a testament to my high standards when chocolate is involved! Nevertheless, Hendrixx Belgian Bakery delivered a truly delightful experience. (100 E Walton St, Chicago, IL 60611)

• A Baker’s Tale – A genuine smile lit up my face the moment I stepped into this wonderfully charming bakery. A Baker’s Tale captivated us with its adorable ambiance and an astonishing display of incredibly creative baked goods. Deciding on just three items was a genuine challenge, as every single treat looked absolutely sensational! Yet, our selections were perfect, and we savored every decadent bite. The peanut butter s’mores cookie, built upon a homemade graham cracker base, was undoubtedly the most memorable item and something I’m incredibly eager to recreate at home. It was simply incredible! The mocha tart and the chewy peanut butter cookie were equally amazing, and I must confess, we might have happily broken our “2-bite rule” for all three of these exceptional goodies. A Baker’s Tale was, without a doubt, a truly sweet discovery. (2127 W. Division St., Chicago, IL 60622)

• Vanille Patisserie – I stumbled upon Vanille Patisserie purely by chance, and what an exquisite find it turned out to be! Every single pastry was a miniature work of art, so visually stunning and impeccably presented that I almost questioned if they were real. The delightful staff behind the counter enthusiastically recommended their Royale Dessert, and their description of its amazingness was incredibly accurate. Each mouthful was pure bliss: layers of delicate hazelnut crust, rich chocolate mousse, luscious salted caramel, and a decadent dark chocolate ganache. Do I need to say more? It was absolutely amazing! I would eagerly return to Vanille Patisserie to sample every other beautiful pastry they have on offer. (2108 N. Clark St., Chicago, IL)

• Little Goat Bread – Foodies are likely familiar with the renowned The Girl & The Goat, but you might not know about its charming little diner and bakery situated directly across the street. This place is an absolute gem! We made our way to the bakery first while waiting for a table to order brunch from the diner. We were so enticed that we ordered almost one of everything the bakery offered! Highlights included a unique goat cheese bagel, a fragrant blueberry & fennel scone, a zesty lemon & chocolate scone, a delightful strawberry banana gluten-free muffin, and several outrageously good cookies. The bakery bar is primarily take-out, but we were lucky to find some standing room at the diner bar, allowing us to savor our treats with iced lattes while awaiting our brunch. It’s clear that the team behind Little Goat possesses exceptional baking prowess—everything was simply fantastic! (820 W. Randolph St., Chicago, IL 60607)

• West Town Bakery & Diner – This was another delightful bakery we stumbled upon serendipitously. As we walked by, a quick glance inside revealed an astonishing array of baked goods stretching as far as the eye could see. Before we knew it, we were seated with a tray brimming with tantalizing sweet treats. Everything looked so appetizing, we debated where to even begin! The fillings, toppings, coatings, and flavors were all incredibly delicious. We were genuinely blown away, surprised that this little find hadn’t been on our initial radar. I’m already planning to recreate their exquisite French toast cake balls and the indulgent peanut butter-filled long johns. Truly a sweet discovery! (1916 W. Chicago Ave., Chicago, IL 60622)

• Hoosier Mama Pie Company – My excitement soared as we finally stepped into this cozy little pie haven. We were warmly greeted by friendly faces, a scattering of charming antique tables, and a dazzling glass case filled with an irresistible selection of beautiful pies. Discovering they offered a “pie flight,” we immediately signed up, adding a few extra slices we simply couldn’t resist. It was officially pie time, and we were pumped! Oh my, what incredibly tasty pie it was! The banana cream emerged as our absolute favorite, closely followed by the rich chocolate pecan, the subtly spiced ginger custard, the refreshing orange cream, and the tangy strawberry rhubarb. This delightful spot is truly brimming with comfort and deliciousness, a perfect place to indulge in a slice of heaven. (1618 W Chicago Ave, Chicago, IL 60622)

Other Sweet Treats: Indulging Beyond the Bakery Aisle

Chicago’s sweet scene extends far beyond traditional bakeries, offering a diverse array of delightful confections to satisfy every craving. Our journey led us to some truly remarkable spots, from artisanal gelato to classic candy shops and vibrant farmer’s markets. Prepare to tempt your taste buds with these extraordinary finds.

• Black Dog Gelato – This gelato shop absolutely blew us away, setting a new benchmark for frozen desserts! Without a doubt, it’s the finest gelato we’ve ever tasted in the United States, and quite possibly even surpasses many we’ve enjoyed in Europe. The flavors were astonishingly creative and complex, a true testament to their artistry. We found ourselves sampling nearly every single flavor before realizing we were holding up the line and needed to make our incredibly difficult final two choices. We ultimately settled on the divine goat cheese cashew caramel and the refreshingly unique strawberry balsamic. Both were heavenly! From this point forward, all other gelato will be compared to the exceptional standards set by Black Dog Gelato—it’s going to be a tough act to follow! If you’re in Chicago, run; don’t walk, to this incredible place! (859 N. Damen Ave, Chicago, IL 60622)

• The Fudge Pot – Stepping into The Fudge Pot felt like a nostalgic journey into a classic candy shop, brimming with an irresistible assortment of fudge, chocolates, caramel apples, and every kind of candy imaginable. When I inquired about their most popular item, the staff member, without hesitation, presented me with a thick piece of toffee almost the size of my head! I could hardly wait to sink my sweet teeth into it. It was a beautiful day, so I found a charming spot outside, by an old-fashioned mural adorning the candy shop’s brick wall. This toffee was, without a doubt, some of the tastiest I’ve ever eaten. And, just as predicted, half of it vanished in no time. It was truly a delightful indulgence! (1532 N. Wells St., Chicago, IL 60610)

• Green City Farmer’s Market – On a beautiful Saturday morning, we made our way to the bustling Green City Farmer’s Market in Lincoln Park. The market was a vibrant tapestry of tents, overflowing with an abundance of fresh, local produce and artisan goodies. It was an absolute joy to leisurely stroll through, sampling a little bit of this and a little bit of that. I had heard whispers of a place called Carnitas & Cookies that regularly sets up shop here, and we were eager to experience its unique offerings. What a fantastic combination! The cookies were exceptional (especially the unforgettable iced bacon one!), and the carnitas taco was simply perfect—mmm! We also sampled a delectable rhubarb loaf and a savory whole-wheat pretzel from other local bakeries present. There’s something truly special about a good farmer’s market, and this one certainly did not disappoint! (Lincoln Park)

• Dollop Coffee Company – We arranged to meet some friends for coffee that Saturday morning, and Dollop Coffee Company proved to be a wonderfully hip and bustling spot! Naturally, I opted for a Nutella mocha and a cookie for breakfast, because, well, that’s just what I do! Who says you can’t enjoy cookies and chocolate to start your day? We also couldn’t resist ordering their appealing cinnamon chip scone, which was love at first bite. It was a truly sweet and delightful way to kick off a Saturday morning. Absolutely loved it! (4181 N Clarendon Ave, Chicago, IL 60613)

• Garrett Popcorn – We had promised our son, Baker, that we would bring back some popcorn, so a stop at Garrett’s was absolutely essential! This establishment is a true Chicago classic, and they undeniably know how to craft perfect popcorn. The renowned Chicago Mix, a delightful blend of savory cheddar and sweet caramel corn, is an obvious choice, but the caramel cashew crisp completely won me over. It’s incredibly amazing and utterly addicting! A visit to Garrett Popcorn is an absolute must if you find yourself strolling along the magnificent mile.

• Mindy’s Hot Chocolate – Our visit to Mindy’s Hot Chocolate was perfectly timed. Though it had been a hot day, a storm was approaching, causing the temperatures to drop and light sprinkles to begin falling. A comforting cup of hot chocolate sounded absolutely perfect. Specifically, a rich dark hot chocolate crowned with a floating scoop of espresso ice cream! It was incredibly rich and utterly delicious. We couldn’t possibly leave Mindy’s without sampling her acclaimed cookies. She’s renowned for her baking brilliance, and tasting her creations was an honor. The thoughtful flavors and high-quality ingredients made each cookie extra special. We savored every single bite! Mindy’s Hot Chocolate was truly a delightful and memorable treat. (1747 N. Damen Ave., Chicago, IL 60647)

Chicago Pizza: Beyond the Deep Dish Delights

On Saturday, our culinary quest shifted focus to pizza. Having already experienced the famed Chicago-style deep dish from all the celebrated establishments on previous visits, we set out on a mission to discover some of the city’s finest non-Chicago-style pizzas. Of course, we couldn’t resist sneaking in one glorious deep dish for a truly well-rounded and victorious pizza tour! Here’s our delicious rundown…

• Piece Pizzeria & Brewery – This lively establishment masterfully churns out pizza after pizza within its bustling brewery, and they do it exceptionally well! Even in the middle of the afternoon, the place was packed, and after just one bite of their pizza, we understood why. They offer a thin crust that achieves the perfect balance: wonderfully crispy yet still pleasantly chewy, generously covered in fresh ingredients and an abundance of delicious cheese. It was sheer perfection! (1927 W. North Ave., Chicago, IL 60622)

• Homeslice Wheel House – We discovered Homeslice Wheel House purely by chance, drawn in by the irresistible aroma of garlic and baking crusts wafting from a block away. We are incredibly grateful for that serendipitous encounter! This spot exuded such a cool, inviting vibe, perfectly complementing the awesome pizza they served. The thin, crispy, and wonderfully bubbling crust was absolutely amazing, and the toppings burst with freshness and vibrant flavor. We absolutely loved everything about it! (938 W Webster Ave, Chicago, IL 60614)

• Pequod’s – We had heard fantastic things about this particular pizza joint, so we knew we had to give it a try. While the service left a little to be desired, the cheesy, greasy, glorious goodness of their pan pizza more than compensated for it. The crust, baked in a seasoned skillet, was incredibly flavorful, and the generous layers of cheese and meats were both indulgent and absolutely delicious! We also tried the thin crust, but in hindsight, we wished we hadn’t, as it unfortunately reminded us of the pizzas served in school cafeterias—not very impressive at all! When you visit Pequod’s, definitely stick to the pan pizza; it’s a guaranteed winner! (2207 North Clybourn Ave., Chicago, IL 60614)

• Brick’s Pizza – What an exceptionally cool experience this place offers! You embark on a journey down a dimly lit hallway, leading to an underground restaurant and bar, equally atmospheric and dark. Here, they serve up a cracker-thin crust pizza that, despite its delicate nature, beautifully supports a wealth of tasty toppings. It’s undeniably distinct, but it truly stands out in the best possible way, offering a unique pizza experience unlike any other. (1909 N Lincoln Ave, Chicago, IL)

• Dimo’s Pizza – The final stop on our extensive pizza tour brought us to Dimo’s Pizza, a vibrant fast-casual spot serving up pizza by the slice. This place impressed us with some of the most interesting and exciting topping combinations we’ve ever encountered. We boldly opted for the BBQ chicken bacon ranch slice and, incredibly, a mac & cheese slice! Yes, you read that right—mac & cheese on pizza! Crazy, right? It was actually pretty darn good! Eating it made me feel like a kid again, and I savored every fun and tasty bite. (3463 N Clark St, Chicago, IL 60657)

Chicago’s Fine Dining & Casual Eateries: A Diverse Culinary Journey

Each evening, we immersed ourselves in Chicago’s renowned dining scene, exploring a selection of fantastic restaurants offering more gourmet fare. One night, we even embarked on an ambitious progressive dinner, visiting three distinct establishments with a strategic movie break in between the second and third to ensure we had ample room for the grand finale! Prepare to be inspired by some truly delicious dishes from these unforgettable Chicago restaurants…

• Avec – Avec was nothing short of extraordinary! From the impeccable service to the exquisite sweets, it stood out as one of the most enjoyable dining experiences we’ve ever had. The communal tables fostered a welcoming and convivial atmosphere, and every dish served was simply wonderful. It was evident that immense thought and passion were poured into each creation. We indulged in bacon-wrapped chorizo-stuffed dates, a refreshing sugar snap pea tabbouleh, creamy whipped brandade, savory chicken liver crostini, luxurious ricotta-filled truffle focaccia, their housemade Nutter Butters (mmmm!), and a rich chocolate hazelnut budino. The bread served was among the best we’ve ever tasted—perfectly toasted with a hint of garlic and oil. An absolutely unforgettable culinary experience! (615 W Randolph, Chicago, IL 60661)

• The Purple Pig – This restaurant exceeded our already high expectations, which were fueled by glowing recommendations! We dined here late, close to midnight, yet the quality of the food and the exceptional service felt as though they had just opened for the evening. Sitting out on their charming patio by the river made for such an enjoyable experience. This was, without a doubt, one of the best meals we’ve ever had, and one we are determined to recreate at home. We savored Greek cornbread, delightful salted Greek yogurt balls with strawberry pistachio preserves, uniquely delicious fried pig ears with crispy kale and a fried egg, and last but certainly not least, an amazing warm ricotta chocolate-filled brioche. We were absolutely captivated by how delicious everything was and eagerly await the chance to return someday! (500 N Michigan Ave, Chicago, IL 60611)

• Sunda New Asian – Brandon had experienced Sunda before and loved it so much that he knew I would too, making him excited to take me back! Their pho was incredibly flavorful and unlike any we had ever tasted. The rich broth was enhanced with Wagyu ribeye, tender bison short rib, and succulent bone marrow, alongside all the traditional pho fixings. It was absolutely fabulous! We also enjoyed perfectly steamed buns, filled with either crispy duck or savory pork belly, all complemented by a spicy, jalapeno-infused gin cocktail. This is truly a great, great place for an exceptional Asian dining experience! (110 W Illinois St, Chicago, IL 60654)

• XOCO by Rick Bayless – The long line snaking out the door of XOCO instantly heightened our excitement and set high expectations. This fast-casual eatery, helmed by celebrity chef Rick Bayless, offers a fantastic selection of Mexican-inspired dishes. The absolute highlight of our meal was the carnitas torta, known as Ahogada, submerged in a spicy, thick tomato and chile broth perfect for dipping. The torta itself was deceptively simple yet bursting with incredible flavor, making us want to keep dipping and eating indefinitely—so, so yummy! While the chicken pozole was a bit bland for our taste, it wasn’t a significant issue as the torta was generously sized, and we were determined to finish it. For dessert, the pistachio churro was undeniably the star! We even enjoyed more of XOCO’s tortas at the airport before our flight home, paired with their loaded guacamole, and it was equally awesome! (449 N Clark St, Chicago, IL 60654)

• The Little Goat Diner – The wait here during lunchtime on the Friday we visited was incredibly long, so we opted to stand at the bar to order the single dish we had come for: the legendary Bull’s Eye French Toast. You might want to sit down for this description! Imagine a perfectly runny fried egg gracefully covering a sweet onion brioche, generously drizzled with perfectly fried chicken, fresh, sweet strawberries, and the most irresistible BBQ maple syrup. Forks down, this was hands-down the best French toast we have ever eaten. It was an absolutely amazing and unforgettable culinary masterpiece! (820 W. Randolph St., Chicago, IL 60607)

• Quartino – This place was absolutely bustling on a Friday night, filled with a diverse crowd ranging from large groups of friends to charming couples on date nights. It certainly felt like a “see and be seen” spot, popular with both locals and tourists. We visited with friends, which made it ideal for sharing several of their delightful Italian tapas. We began with an awesome salumeria tasting platter, overflowing with various meats, cheeses, olives, and spreads. Next, we savored a pizza topped with savory meatballs and spicy giardiniera. Our savory selections were rounded out by a fresh caprese salad, a rich truffle risotto, and delicate pesto gnocchi. We were so glad we saved room for dessert because the hot Italian donuts, served with honey and dark chocolate, were absolutely to die for! Quartino was a fantastic place to satisfy our craving for authentic Italian food in a city renowned for its exceptional Italian cuisine. (626 N State St, Chicago, IL 60654)

• Picante Taqueria – After indulging in so many sweets, we found ourselves on a sugar high and desperately craving something salty. Some fellow foodies we met in a quaint little art shop highly recommended the tacos from Picante Taqueria just down the street, so we practically ran there! This al pastor taco was the real deal—authentic, bursting with flavor, and absolutely awesome! It was the perfect savory antidote to our sweet overload. (2016 W Division St, Chicago, IL 60622)

• Sable Kitchen & Bar – Our grand finale to this epic culinary feast through Chicago was at Sable Kitchen & Bar. This restaurant seamlessly blends new American cuisine with a gastro-pub sensibility, offering an outstanding selection of creative cocktails. We dined late, around midnight, which made for a wonderfully quaint atmosphere, and the service was truly exceptional. It was clear that everyone, from our waiter’s knowledgeable recommendations to the chef who personally came out to answer our questions about a particularly amazing dish, took immense pride in their establishment. We ordered the irresistible bacon jam & toast (definitely recreating this at home!), exquisite black truffle deviled eggs (another must-recreate!), an “evening” bun with kale, parmesan, and spicy chiles (will try this too!), a fresh snap pea & asparagus salad, a remarkable sweet corn crème brûlée (amazing!), and the tender, slow-braised Moroccan lamb (mmmm!). We concluded our meal and our entire trip on an incredibly sweet note with Sable’s rich dark chocolate soufflé cake, served with a decadent peanut butter sauce and salted caramel ice cream, alongside a warm sticky toffee pudding cake! We left Sable with broad smiles on our faces and complete satisfaction in our bellies. A truly great meal and an unforgettable experience! (505 N State St, Chicago, IL 60654)

Plan Your Own Chicago Food Adventure!

What an utterly delicious and memorable journey through Chicago’s culinary landscape! If you find yourself living in or traveling near the Windy City, we wholeheartedly encourage you to explore some, if not all, of these incredible establishments. Each offers a unique taste and experience that contributes to Chicago’s vibrant food scene. Enjoy your own delightful discoveries!

~Maegan & Brandon