Chicago, where it all began...at least for me. It’s a masterpiece in American history, full of culture and contrast. Chicago offers tremendous diversity across a series of segregated communities. It’s one of the cleanest and most promising major cities you will find; home to some of America's greatest heroes such as Hilary Clinton, Michelle Obama, Earnest Hemingway, Coach K, Walt Disney, Homer Simpson, and Al Capone.
Although far from perfection, Chicago has it all - great food, great sports, great people. Though it’s not a coastal town, Chicago even has a beach scene. It's not as busy as New York, has less traffic than LA and is smaller than both. But show me a person who doesn't like the Windy City.
Fortunately (or unfortunately) Chicago has 4 seasons, but visitors experience the City at its best in the spring or summer. During this time of year, you will be surprised by the number of festivals and outdoor activities Chicago can offer. Year-round, Chicago is an absolute culinary showcase. Save room for desert, and enjoy my first home, the Second City, and all it has to offer!
Day 1 – Pilsen, Bridgeport & Further South: Art, tacoS and the Art of Eating
If Chicago has a soul, it probably smells like carnitas and wet paint, drinks cheap beer in Bridgeport, and still hates the Cubs.
Café Jumping Bean — An OG neighborhood coffee shop dripping with mural art, brown sugar lattes, and genuine South Side pride. Writers and abuelitas share tables here.
Pilsen Murals — The murals in Pilsen aren’t just paint on brick — they’re history, protest, pride, and poetry baked into the walls by decades of immigrant hands and restless hearts. You don’t just look at them; you feel the weight of stories about struggle, joy, and identity, told in colors loud enough to drown out the El train. Walk these streets and you’re not just in Chicago — you’re in a living, breathing art gallery that refuses to be quiet.
Carnitas Uruapan — No pretense. Just expertly crisped carnitas, salsa cruda, and warm tortillas stacked on metal trays. Eat with your hands and forget your name.
Giordano’s — It’s a well known chain now, but it’s the spot for square pizza and deep dish heaven that I was raised on. Other local favorites are Pequods in Lincoln Park, George’s in Edgewater or your favorite local tavern.
National Museum of Mexican Art — Deep, emotional, beautiful. A free museum that punches way above its weight, with murals and Dia de los Muertos altars that’ll crack your ribs open.
Ricobene’s — The breaded steak sandwich has been named the best in the world. Yet, it's probably Chicago's, no, America's most underrated sandwich. But Ricobene's has more than one specialty. They are also home to the best buffalo wings I have EVER tried. That's no exaggeration folks. And as a consummate consumer of wings, I stick by my statement. Oh, and try their fries if you can find room.
Leon’s — You walk in, and you're immediately hit with that smoky, sweet, tangy aroma, the scent of slow-cooked meat promising something truly special. You order a full slab, because frankly, anything less would be a crime. It's a messy affair, hands sticky, face smeared with sauce, but every bite brings pleasure. By the way, I wouldn’t fault you for visiting Harold’s Chicken Shack or Lem’s Bar-B-Q all in one trip!
Duck Inn — The Duck Inn is where comfort food grows up, gets a degree in charm, and still remembers how to have a good time. The rotisserie duck — crisp skin, tender meat — is the star, but it’s the kind of place where even the hot dog feels like a culinary love letter to Chicago. Warm lighting, a touch of retro swagger, and cocktails that make you linger long after the plates are cleared — it’s dinner as an embrace, with just enough edge to keep it interesting.
Day 2 – It’s All West loop to me: Foodie Culture
Wake up, pull back the curtain and get your fill of “old Chicago” plus new digs where chefs push boundaries. Get there before all these damn college students consume everything the light touches.
Drip Collective — Here, lattes come draped in ube and Ovaltine and zombies of gochujang rancor. Walls flex the work of local artists. Vinyl spins on DIY DJ nights. You don’t just drink the coffee—you soak up the unlikely energy of a café double-daring as a pop-up gallery, soundstage, and creative nexus.
Lalo’s — I realize there are infinite amazing Mexican restaurants in Chicago. However, the only one that holds a special place in my heart is Lalo's. I was ride or die for Lalo's back when there was only a single location in Berwyn, IL. Nothing beats their fajitas, amazing Sopas, and frozen daiquiris.
Jim’s Original / Carms — When you come to Chicago, you order a hotdog. Get it dragged through the garden- tomato, relish, mustard, onions, a pickle, sometimes peppers! Oh, and remember, no ketchup! Jim is the first name every Chicagoan knows. It’s a hole in the wall and a "must visit" for the true spirit of Chicago. Another option is Carm’s - definitely a sleeper. It’s nestled within Chicago's Little Italy next to Sheridan Park, where one Weekend Pilgrim founder once crushed home runs. As a child, I ordered a cheese dog, fries and an Italian Ice every week. As an adult, I can't wait to return to see the same familiar faces that served my family with a file over 30 years ago. Carm's is timeless and I hope they will be around forever.
Mickey’s Gyros & Ribs — This one requires a bit of a commute, all the way to the suburb of Oak Park. The gyros come loaded, dripping tzatziki onto the paper wrapper, while the ribs are messy, unapologetic, and exactly as sticky-fingered as they should be. However, the best order is the “Big Mickey” - my favorite burger in the world! They filled by best high-school memories and used to cost a buck. Now, you can still get 2 for just over $4!
The Publican — Ah, The Publican- one of Fulton Market's finest. The food is excellent and is nearly matched by a quality selection of beer and creative libations. Start with pork rinds or The Publican's famous homemade bread plate. We couldn't find an appetizer we didn't like. Their dinner menu is awesome and changes with the seasons. However, try the Publican for brunch- you won't be disappointed.
Girl and the Goat — Girl and the Goat reigns supreme among West Loops hottest restaurants. Take it from a couple that loves to eat- there isn't an item on the menu that you won't want! Fortunately, Girl and the Goat offers family style dining with reasonably sized portions. Ordering 2 items per person ensures your entire dining party will enjoy a multi-course meal at a reasonable price. Try the Duck Tongue and anything with goat in the title!
Greek Islands — Have you seen "My Big Fat Greek Wedding?" If so, you already understand. If not, let me explain! Chicago is home to some of the finest Greek restaurants in the country. "My Big Fat Greek Wedding" takes part in Chicago's "Greek Town" and gives you a glimpse into the magic of the restaurants that fill this West-Loop neighborhood. Our favorite is Greek Islands, which is the self proclaimed "most famous Greek restaurant in America.” Try the grilled octopus, saganaki, or any lamb dish on the menu.
Kasama — Kasama isn’t just a restaurant — it’s a love letter to Filipino flavors, written with a fountain pen dipped in duck fat and sugar. By day, it’s a bakery where the aroma of ube and buttered croissants could bring a grown man to tears. By night, it flips the switch into a tasting menu that’s part family history, part fever dream, each dish plated like a memory you didn’t know you had. It’s not about fusion or gimmick — it’s about two people cooking food that matters to them, and daring you not to fall in love.
Day 3 – Downtown Chicago - The Loop
You weave through steel towers into stained-glass sanctuaries and basement speakeasies—Chicago’s heart is palpable in the quiet corners with more than a touch of tourism. Sprinkle any left-over food recommendations from the first two days into your breaks on Day 3.
Art Institute — Beijing has the Palace Museum, Paris has the Louvre, New York has the Met, and the Second City has the Art Institute of Chicago. I can't travel home to Chicago without a visit to this downtown temple of the arts. Explore a truly diverse collection from medieval throne rooms to Indian Art of the Americas to Rembrandt. Its miniatures exhibits will make you buy a dollhouse. Lose yourself for at least 2 hours!
Millennium Park & Grant Park — Jack's magic beans were much smaller. Feast your eyes upon- The Bean at Millennium Park. Although it's known as an awesome destination for children and their families, Millennium Park is host to free concerts, films, nature programs, and exhibits. Keep walking south to find Grant Park - a picturesque landscape nestled between Lake Michigan and Chicago's skyline. It’s the home of the Taste of Chicago and a variety of other festivals. It is the neighbor to Chicago's nearly 16 miles of white sandy beach. Visit for some of the most breath-taking photos or for a simple afternoon in the park.
Water Tower and the Mile — Once upon a time (1871 to be specific), the Chicago Fire destroyed the majority of Chicago's building and landmarks. However, one of the only structures that survived the great fire was- Spoiler Alert- the Water Tower. This historic landmark, originally built two years prior in 1869 remains in tact today within downtown Chicago. Located just steps away is the Water Tower Place and several high-end shopping establishments within Chicago's Magnificent Mile. Definitely make this a stop (at least once) for great shopping, dining, and people watching.
Garrett Popcorn — Close your eyes and imagine a mountain of delicious caramel corn. That's what you will see at Garrett's. It actually melts in your mouth. Try it. Well, to be specific, you must try the Chicago Mix with a blend of cheese and caramel corn. This popcorn is a staple of Chicago and lines of locals and site-seers wrap around Chicago blocks throughout the year. Garrett Popcorn was almost featured at my wedding- really. Get a small bag and then have a bin shipped home.
Navy Pier — Sitting between Lake Shore Drive and Lake Michigan is Navy Pier. There's something for everyone here. You can find a throw-back to the World's Fair ferris wheel of 1893, Shakespeare Theater, Children's Museum, Imax, restaurants, arts, shopping, and boating options across Lake Michigan. Kids will love this touristy destination which often hosts fireworks throughout the Summer. Adults will love the scenery and great food and beverage options such as a Beer Garden overlooking the lake.
Lake Michigan — Not too far from Navy Pier, or along Chicago’s 28 miles of shoreline, is a stunning lakefront so vast, you would share you’re on the ocean. No, it’s not quite Miami, but Chicago boasts 24 different sandy beaches. Those tall buildings are even more beautiful when touring the lake by boat.
Asador Bastian — Asador Bastian is a steakhouse that plays by its own rules — the kind of place where meat isn’t just cooked, it’s worshipped. You walk in and the air smells like fire, oak, and the slow, primal patience of dry-aged beef pushed to the edge of perfection. The menu is unapologetic, the kind of thing that says, if you don’t like it, order chicken somewhere else. Every bite has that faintly dangerous quality — like you’ve tapped into something older and wilder than polite dining. This isn’t just about eating steak. It’s about remembering why humans started cooking in the first place.
Buddy Guy’s Legends — Buddy Guy is a legendary blues guitarist and singer. He has influenced guitarists such as Hendrix, Clapton, Page, Richards and played with Muddy Waters in the 60's. Buddy is a Chicago icon. He’ll turn 90 in August, 2026 and continues to grace the stage as if to give you a glimpse into history. Visit Legends to witness great, pure, classic blues from various artists from Chicago and across the globe.
Day 4 – North Side
Head north to the gold coast, and then keep going to chase ethnic dishes at 2 a.m., and a speakeasy behind a flower shop. Once you know, everyone knows.
Wrigleyville — If you like baseball- wait- if you like America, Wrigley Field is a must do. Wrigleyville is home to the Chicago Cubs, their home stadium Wrigley Field and a host of bars that just simply make life better. I have nothing against the Sox- Good Guys wear black. But, lets face it, Cubs fans have more fun (sorry to my blond friends). Wrigley Field is likely on the list of must-see stadiums for baseball fanatics, but its highly recommended for all, regardless of your sports affiliation or hobby. And while you will be inclined to "root, root, root for the Cubbies," just don't expect a win for the home team!
Rainbow Cone — We put this here, but Rainbow Cone’s are all over the city. Rainbow Cone is pure Chicago nostalgia stacked in five unapologetically mismatched layers — chocolate, strawberry, Palmer House, pistachio, and orange sherbet — like some reckless dare from a sugar-drunk genius in 1926 that somehow stuck. It’s not fancy, it’s not delicate, and that’s the whole point. One bite and you’re eight years old again, no matter how many bad decisions you’ve made since.
Kuma’s Corner — Without exaggeration, eating at Kuma's makes me want to quit my job and open a burger joint. The only thing stopping me is knowing that, no matter how hard I try, you just can't do any better than Kuma's. Let the menu do the talking. Try the Iron Maiden, Lair of the Minotaur, Led Zeppelin, or Goatsnake. Yes, these are the names of various burgers that are absolutely awesome. Yes, Kuma's likes heavy metal and it blasts from the speakers daily! Oh, and did I mention Kuma's lets you customize your own mac n cheese which is made is a cast iron skillet- also awesome! All of that combined with a great beer selection makes Kuma's a must visit in Chicago.
Gibson’s — Gibson's is a class act among steakhouses. In fact, it probably has a home among the Mount Rushmore of Chicago restaurants. If you like steak- thank me later. If you like small portions, scroll ahead. You can't go wrong here. Try any of Gibson's corn fed, sustainable farm raised, 40-day aged black angus and your trip to Chicago will be fulfilled.
The Library Speakeasy / Blue Agave — The Library offers velvet booths, vintage spines, and a hidden door that served gin when it wasn't “legal”—this is the city’s soul in cocktail form. As a night and day alternative, try Blue Agave. It’s rare to find a restaurant with great food in a fun atmosphere. Blue agave specializes in great drinks that are great in size. Try one of their 150+ tequilas and/or tasty margaritas!
Annapurna (DEVAN ST.) — It’s my late-night happy place. After a night on the town, why eat Pringles out the can, when you can have some of the best Desi food in America on Devan Street!
Ravinia — Just north of the Chicago city limits sits Ravinia. This summer destination in Highland Park, IL hosts regular concerts in an outdoor arena. Come here with friends for a great afternoon filled with music, food, and drink, on a picnic blanket.
Funkytown Beer — They are the present and future of the City and stacking beer trophies across America. Great beer, currently at Pilot Brewing and coming to the near west side around the United Center. Until then, order in more than 100 locations across the City.
