It’s official — Chicago has been named the best big city to visit in America for the fourth year running (according to Conde Nast). Since moving to Chicago, I’ve heard the phrase “world-class city” thrown around a lot. As the third largest city in the U.S., Chicago’s location gives it a different feeling than the coastal megacities, boasting its own working-class, heartland pride while still being a global hub of immigration and innovation like New York City or Los Angeles. Downtown Chicago has the glitz and glamour of Madison Avenue or Beverly Hills, but its neighborhoods and suburbs are fundamentally shaped by the diversity of the people who live in them, not by any cosmopolitan consideration. An itinerary that covers ground across a lot of them is ambitious, but is the best way to get a sense of the culture in Chicago. 

Former mayors Roger Daley and Rahm Emmanuel talked a lot about transforming Chicago into a world-class city, but on account of the myriad of cultural experiences you can have here, it has always been one. While travel was limited this year, I had the chance to explore the kaleidoscope of culture in Chicago more intimately than I otherwise might have, and I very rarely felt disconnected from the world as a result. This leads me to only one conclusion: you can travel around the world within the confines of Chi-town. In this Chicago, Illinois travel guide, I’m going to show you how! 

chicago italian beef stand

A Taste of Central & South America in Pilsen 

Any Chicago itinerary would be in complete without a day spent in Pilsen. Located about 15 minutes southwest of downtown by the L or by car, Pilsen is a predominantly Spanish-speaking, nationally registered historic neighborhood with a significant Mexican-American and Mexican population. Initially home to Eastern European immigrants who inspired its name (after Plzen in the Czech Republic), changing demographics brought diverse and incredible traditions of food, mural-making, sport, and music. Gentrification in recent years has increased its popularity across the country — leading Forbes to name it one of the coolest neighborhoods in the world last year — but a walk down 18th Street will leave you with no doubt that this is el corazon de Chicago, matcha-mad hipsters or not. 

There are so many places to get good food in Pilsen, so I can’t possibly cover them all. I’ve lived in the neighborhood myself for 6 months and discover a new, amazing spot every weekend. With cozy sit-down experiences, street food galore, and tacos pretty much everywhere you look, a walk through Pilsen is both dizzying and delicious. 

blue taco restaurant exterior

Some of the neighborhood’s sit-down staples include 5 Rabanitos, La Mejikaña, La Vaca, Azul 18, and Taqueria Los Comales. There’s a really wide variety of dishes available at all these restaurants, catering well to different tastes and dietary preferences. As a vegetarian myself, I’ve had a lot of ease, success, and enjoyment dining at these establishments. At 5 Rabanitos, I particularly recommend the papas a la plaza (sort of similar to Catalan patatas bravas without such a spicy kick) and any of their huaraches. At La Mejikaña, you can’t beat their fresh garden salad or the mushroom and spinach empanadas. At La Vaca, get a tamarind margarita and the vegan fried oatmeal taco — seriously. At Azul 18, the chilaquiles and beignets are a must. Finally, at Los Comales, just get tacos, any kind and number you like. Can’t go wrong. 

With those essentials covered, let me talk about a few places and dishes in Pilsen that are near and dear to my heart. There are any number of ice cream places in the neighborhood, but for dessert or a mid-day treat, La Michoacana Premium on Blue Island is unmatched. They have traditional flavors and some that are more playful, inspired by popular Mexican candies. If coffee is your post-meal preference, Cafe Jumping Bean (and its diminutive counterpart, L’Cafecito Jumping Bean) has a well-earned reputation as the place to get your caffeine fix in Pilsen — special shout-out to their veggie focaccia sandwiches, too. 

El Milagro Tortilleria, in addition to supplying delicious tortillas and chips to Pilsen’s grocery stores, has a cafeteria-style eatery where you can grab amazing food to-go, such as deliciously cheesy and spicy chilaquiles. My favorite under-the-radar spot to grab tacos or a quesadilla is a grocery store called the Cermak Fresh Market at W Cermak and S Paulina — they have a grill and deli that slings amazing chile relleno tacos. If you’re uninitiated, these are poblano peppers stuffed with cheese, deep fried in egg batter, and put in a taco. Heaven on earth.

el milagro tortilla factory in chiago
mural of selena

Last but not least, Carniceria Maribel and the Parkview Diner are two of my favorite places to grab a bite within walking distance of my place. The former is a corner store with a huge mural of Selena on its outside, an amazing taqueria at the back, and some of the nicest owners. The latter is a perfect place to sit and read the paper on the weekends and warm up from the notorious Chicago winters with some french toast or chilaquiles. Basically, If you’re looking to flesh out a weekend itinerary in Chicago, be sure Pilsen is at the top of the list.

Places that deserve a quick shout-out include Carnitas Don Pedro, Casa Indigo, and Bob’s Pizza


Italian cuisine has combined with Chicagoan innovation to bring the world some famous Italian beef, Italian ice, deep dish pizza, deep dish pizza, and… deep dish pizza. It’s hard to pick just one food staple that defines Chicago, with the city’s signature hot dog and delicacies like Polish sausage also attaining icon status around the country (and the world). But beyond Chicago-style Italian food and all the wonderful dishes that represent the intersection of those two cultures, the city and surrounding area are overflowing with quintessential — and quirky — Italian landmarks. 

pink ice cream shop in chicago
blue and pink cafe exterior

While there is a Little Italy, home to the legendary Jim’s Original, you can find good Italian food spread out across many of Chicago’s great neighborhoods. My first experience was at Club Lucky in Bucktown, on the corner of N Honore and W Wabansia. This old-school supper club curates its vintage vibe with exposed brick, art deco bar decor, and sophisticated cocktail offerings like my favorite “paper plane” aperitif: Amaro Nonino, Maker’s Mark, Aperol, and lemon juice. Combine with the fried calamari and mozzarella fritti to start and you’ll be ready for the hearty, home-made taste of one of their signature parmesans, pastas, or marsalas. 

A pleasant walk up Milwaukee Avenue from Club Lucky’s corner of Bucktown will deliver you to your first taste of Italian ice in the city at Ava’s. Claiming to be “Chicago’s healthiest Italian ice,” probably in catering to the trendy nature of their block, Ava’s signature offering is their “ice flight,” much like the kind of flights you might have at a brewery or whiskey bar — but, you know, with ice. 

Next, we’ll head to the West Loop on the corner of N May and W Grand, which might be the most delicious intersection of the entire city. Here you’ll find Bari Subs and Italian Foods, next to D’Amato’s Bakery. Both are bonafide sandwich institutions in the Chicago deli scene, and the fact that you can visit both in one trip (and even visit Vinnie’s down the road if you’re still hungry) is unbeatable. The former offers a quintessential bodega experience, with authentic Italian grocery items and a deli with the famous sandwiches towards the back. Go for a meatball or veggie sub, and grab yourself a jar of giardiniera to eat as a side with every meal you have for the rest of the week. Then, pop over to D’Amato’s to grab one of the best cannoli’s in the city. 

club lucky in chicago

A few blocks east on grand is another sit-down that is reminiscent of an Italian grandmother’s kitchen: La Scarola. This place embodies comfort, from friendly staff to full-bodied portions with minimal wait-time. Once again, the eggplant parmesan steals the show, though the broccoli and goat cheese pasta with gnocchi or rigatoni is a close runner-up for the pick of the house specialties. 

Last, but certainly not least, let’s talk about pies — pizza pies. There are of course two major chains offering deep-dish pizza in Chicago, and the debate rages on about which is better. Just like you’re either a Cubs or a White Sox fan, it’s contentious and important whether you reach for a slice of Giordano’s or Lou Malnati’s. Fortunately, both have locations all over the city, so you can easily decide for yourself during your visit. There are several other notable pizza establishments though, with just as much history and deliciousness baked in to their pies. On the north side, there’s Pequod’s, a pub-style dive that garnered a cult following for doing their deep dish in a cast-iron skillet. On the near south-side in Bridgeport, Ricobene’s and Phil’s Pizza have attained local legend status. The former is the neighborhood go-to for deep dish, while Phil’s square-cut, thin crust pie is the perfect comfort food, served up no-frills at a counter-serve, cash-only location. 

giordano's pizza in chicago

A “Famous” Landmark and Korean BBQ

One Italianate oddity worth mentioning in the Chicago area is the leaning tower of Niles, which, as it sounds, is a replica of its namesake in Pisa — located in the northwestern suburb of Niles. If you’re in the mood for this oddball detour, the good news is you’ll be rewarded with some awesome Korean food. That’s because Niles is home to Chicago’s “new Koreatown,” after the original Koreatown gentrified and many Korean immigrants had to move this way. Should you decide to make the trip, here’s a handy guide to 38 of the best spots for Korean cuisine in Niles’s New Koreatown, according to WBEZ and the Chicago Tribune. Bon appetit.  

The Art Institute of Chicago

It’s been all about food to this point, so here’s an activity that will get you walking around and digesting all that deliciousness. With a gargantuan repertoire of art and artefacts from around the world, the Art Institute is one of the world’s leading museums. Just to give you a sense of the masterpieces on display, they possess works by Matisse, Monet, Picasso, O’Keefe, Dali, Van Gogh, Hockney, Hopper… The list goes on. This may be an American museum, but the story that its collections tell is one of a vast, international creative tradition to which we all belong. You can truly spend an entire day here, browsing the halls of Asian, African, and Native American art before making your way to the impressionists and modernists. I had a chance to visit during this crazy time, and take in their Monet and Chicago exhibit. You can read all about my experience and what it’s like to visit a world-class museum during a pandemic on our blog

art institution of chicago itinerary


Adjacent to the Sox’s home neighborhood of Bridgeport, Chicago’s Chinatown mostly runs along a pleasant stretch of S Wentworth avenue where it meets S Archer, and is loved for its culinary offerings and  great selection of parks. Some of the best views of the Chicago skyline can be found in Ping Tom Park and Henry C. Palmisano Nature Park. The former has kayak rentals for touring the Chicago canal, a beautiful pagoda, and lovely murals depicting scenes of Chinese heritage and life. The latter has a quaint fishing pond, awesome trails, and an expansive hill with city views perfect for a picnic–all a source of peace and quiet in the urban madness. 

blue bike next to yellow oriental mural
chicago skyline with canal

The Wentworth stretch of Chinatown is bustling and photogenic, with a traditional gateway and architecture inspired by Chinese imperial style. Pick up some dim sum, noodles, Szechuan, or Korean food and sit at the intersection of Wentworth and Cermak, where a wide sidewalk gives way to an outdoor-mall perfect for people-watching or taking in the unique views. 

Pubs of the UK and Ireland 

Having lived in the UK for significant portions of my life, a proper pub experience is something I always seek out when I move to a new city. On my very first visit to Chicago, I found a new home for Guinness-drinking and soccer-watching when I stumbled upon the Ambassador in Greektown, owned by Irish folks and full of flat screen TVs perfect for making new friends and enjoying a Bears game. The manager even changed a TV to the Tennessee Titans game at my request, so I could watch my hometown team. I couldn’t recommend this place more, and I’m so glad they survived this year’s recession. 

England, Wales, and Scotland are home to any number of high-brow pubs these days, where the pints are coupled with cuisine of great renown — it’s not unusual for chefs and pub dishes to attract international awards and attention. In a similar vein, Chicago’s Pleasant House Pub serves up authentic savory pies that have earned the establishment a listing in the Michelin Guide, an entry that lauds everything from their fresh regional greens to their mac and cheese. But for all their achievements, Pleasant House keeps pub culture alive and well by curating a mouthwatering list of beer and wine that includes growler fills and multipacks available to-go. Fantastic regional breweries like Three Floyds feature, while they bring in Robinson’s and Wells and Youngs offerings from England. 

The World Tour Encore

Obviously, Chicago is huge, and its immigrant and international stories go well beyond the scope of this article! You can grab Polish pierogi in Belmont, gyros in Greektown, and korma in Little India along Devon Avenue. There’s also some amazing Puerto Rican brunch to be had at Nellie’s in Humboldt Park, a neighborhood where you can find Peruvian and Dominican grub, too. Should you get the chance to see Chicago soon, I hope this itinerary provides you with the resources to get in touch with the tune of our city, which wouldn’t be what it is without the flavors and feelings of the world. Enjoy! 

Did we miss one of your favorite worldly experiences in our Chicago, Illinois travel guide? Let us know on Twitter