If you’re the kind of visitor — or local — who loves to experience a city’s iconic, regional dishes, Chicago is one of the best places to be in the country. This is a place with several inventions to call its own — it even has two competing city pizza
styles (though residents know thattavern-style reigns supreme).
I gave myself a mission on a recent Saturday to experience at least five of these dishes in one day, and I managed to pull it off — with a few welcome bonus stops. Here’s what I did; follow along if you’re interested in embarking on your very own iconic dishes crawl in Chicago over less than a 24-hour period. Bring a friend if you can — you’ll have an easier time conquering all of these dishes if you split them with someone.
Breakfast: Longganisa Breakfast Sandwich at Kasama — 9:30 a.m.
1001 N Winchester Avenue, Chicago
Ok, if we’re being honest here, I kicked off my iconic dish crawl with Stop 2, so I had the opportunity to sleep in a little bit on vacation. But if you want to make the most of your day, here’s a way to squeeze in another dish earlier in the morning; do what I did for my a.m. meal the day before: Order the hyped longganisa breakfast sandwich at James Beard- and Eater Award-winning Filipino heavyweight Kasama (featured in The Bear, among other accolades) to-go. Most of the dishes featured on this crawl have clear roots in Chicago, while this dish is more about the restaurant’s iconic nature. And the demand is clear: Kasama is known for drawing hours-long lines down the street for its offerings.
Do your best to avoid the line situation by ordering pickup exactly at 8:45 a.m. when it becomes available. The TikTok crowd is onto this “hack,” so you’ll still likely have a delay of some sort (my pickup time was approximately 9:30 a.m.), but you won’t have to spend it standing around. The breakfast sandwich is a must, but if you’re not worried about leaving room for the rest of the day’s eating, you can’t go wrong adding an ube latte or one of the fantastic pastries to the mix. Also that mushroom lumpia… forget it! Gotta focus on the crawl ahead. If you’re looking for somewhere to down your sandwiches, there’s a playground with picnic tables called Commercial Club Park just a few blocks away from the restaurant.
Lunch: Italian Beef at Johnnie’s — 11 a.m.
7500 W North Avenue, Elmwood Park
A roughly 25-minute Uber ride from Kasama is Johnnie’s; aim to get to the restaurant around opening, because we’ve got another line-generating restaurant on our hands. I arrived closer to 11:30 a.m. on a weekend and only had to wait a few minutes. Your focus here is on the Italian beef sandwich, a Chicago giant; gravy on the side gilds the lily, but isn’t wholly necessary. The restaurant is cash-only, so come prepared, and the only seating is picnic tables surrounding the stand, which you should take advantage of: This sandwich can get messy. Note that if you need a restroom, you won’t find it at Johnnie’s, but there’s a higher-end grocery store directly across the street.
Lunch Chaser: Peanut Butter Egg Roll at New Star — 11:30 a.m.
7444 W North Avenue, Elmwood Park
You have the opportunity to check another dish off your list while barely leaving the parking lot. New Star isn’t necessarily the most famous location for the peanut butter egg rolls that Chicago calls its own (Orange Garden seems to have the most cred in this department), but it’s been a neighborhood fixture since 1954, and it’s basically next door to Johnnie’s. The front desk didn’t bat an eye when I wandered in and ordered a single egg roll for carryout. The peanut-y sauce calls to mind Thai food more than it does a PB&J: I didn’t notice a dramatic difference from the typical Chinese American egg roll you’re likely to encounter, but I’m still glad I got the chance to try one.
Big Little Treat: Rainbow Cone at Rainbow Cone — Noon
7025 W North Avenue, Oak Park
I noticed too late — when we were already in our Uber — that we had been just over a 10-minute walk from another Chicago great: a location of the Original Rainbow Cone (which my husband and I had previously encountered at our visit to the Shedd Aquarium two days before), which opens at noon. This ice cream purveyor is more than a century old, and the brainchild behind an epic Chicago-based dessert creation that combines five different ice cream flavors sliced (not scooped, they’ll tell you), on top of a single cone: chocolate, strawberry, Palmer House (vanilla with walnuts and Maraschino cherries), pistachio, and orange sherbet. If you’d rather pace yourself than already be sampling dessert by noon, there are other locations scattered throughout the city and suburbs, including many of Chicago’s most touristy neighborhoods.
Second Lunch: Carne Asada Jibarito at Jibaritos y Mas —12:45 p.m.
3400 W Fullerton Avenue, Chicago
You’ve got another 20-ish minute cab ride ahead of you, but I promise that it’s mostly walking from here on. It’s time to head to Humboldt Park, the heart of the city’s Puerto Rican community, to sample a dish known as the jibarito: a sandwich served between two fried and flattened green plantains rather than bread. Steak is the most well-known filling, and what I went for, but here you can find everything from ham and cheese to octopus and shrimp (not to mention blood sausage and even a vegetarian option). Jibaritos y Mas has both a sit-down restaurant and a carryout location next to each other, depending on your preference. If you opt for the former, it may be hard to resist the temptation to order an appetizer-sized portion of the lechon to start (approximately half a pound); I’ll be honest that it nearly upstaged the sandwich for me.
Take a walk
I highly recommend walking the 30 minutes or so between Jibaritos y Mas and Redhot Ranch, even if you make a stop along the way; it’ll give you the chance to digest a little, and give you more of a sense of both the Humboldt Park neighborhood and nearby Logan Square (which also has plenty of cute shops to duck into if you’d like a longer break).
Coffee Break: Caribella — 1:30 p.m.
3311 W Fullerton Avenue, Chicago
I caffeinated with a cameo at Caribella, which is famed for its coquito latte; it’s definitely dessert-sweet, but you probably wouldn’t expect otherwise from a drink flavored with the same accents as the traditional Puerto Rican holiday liquor. After about 15 minutes of walking, we decided to take a more extended break…
Cocktail Break: Daisies — 2 p.m.
2375 N Milwaukee Avenue, Chicago
…and grab a cocktail at Daisies, a beloved Logan Square restaurant known for its pastas, cocktails, formidable happy hour, and sunny vibes. The bar here doesn’t officially open until three, but you can order a drink off the brunch menu: both options available when I was there were garden-y spins on classic drinks, including an earthy beet Manhattan and a kombucha-reminiscent cocktail with carrot in it; the latter offered a bit of a digestif effect that was welcome given all of the eating so far.
Afternoon Snack: Depression Dog at Redhot Ranch — 3 p.m
2449 W Armitage Avenue, Chicago
You can’t go to Chicago without having a hot dog, and there are a lot of restaurants jostling for iconic status in this department. Among them is Redhot Ranch, famous for its Depression Dogs. These feature some of the ingredients of the traditional Chicago-style dog (for example, sport peppers), but Redhot does its own thing by dumping a heap of french fries onto everything. Despite my ties to Pittsburgh, home of fry-topped sandwiches and salads, I didn’t find that I needed this particular accent to my hot dog. Next crawl, I might opt for a visit to nearby JR’s Red Hots instead and order one “dragged through the garden” there for contrast.
Pizza Treat: Tavern-Style pizza at Pizza Matta — 4 p.m.
3211 W Armitage Avenue, Chicago
So I technically had a bit of tavern-style pizza on my Saturday crawl. I’d visited the current hot table Pizz’amici the night before, a place where you can get exceptional tavern-style pies alongside pepperoni Negronis and soaringly high focaccia, and my breakfast earlier this morning had basically been a square of leftover cold pie from that excellent dinner. I’d recommend this restaurant in a heartbeat, but it’s tricky to get into; my reservation for the night before had been at 9 p.m., and its tiny location is not particularly conducive to walk-ins. If you don’t have another opportunity to try tavern-style pizza and want to squeeze it in during this crawl, it’s worth noting that Pizza Matta, a fixture of our tavern-style pizza map, is on the same street as Redhot Ranch, about another 20-minute walk west (which might be welcome exercise given all of the eating).
Nap O’Clock — 5 p.m.
Regardless of whether you’ve snuck in a pizza stop or not, it’s probably time for a break — nap, read a book, do something other than eating for a couple of hours. You need to rest up for your final stops.
Dinner: Shrimp De Jonghe and Vesuvio Potatoes at Gene & Georgetti — 8:30 p.m.
500 N Franklin Street, Chicago
In the heart of Chicago’s River North neighborhood is the classic steakhouse and Italian restaurant Gene & Georgetti, which has been serving up Manhattans, meats, and meatballs since 1941. It’s also a place where you can find not one, but two iconic Chicago dishes, including one featured in Eater’s new cookbook, Eaterland: Restaurants and Stories from Across the United States. The two dishes are shrimp de jonghe, a garlic shrimp dish accented with bread crumbs that can be ordered here as an appetizer, and chicken Vesuvio, a hearty braised chicken dish with lemon and potatoes. If you aren’t feeling poultry entrees, note that you can order a side of the Vesuvio-style potatoes that are prepared in the same manner as the chicken dish, and go well with other options on the menu like steak or branzino. Either way, make sure that shrimp is in your calculation, as well as a cold martini.
Chicago Handshake: Anywhere you fancy — 10:30 p.m.
You can’t leave Chicago without experiencing the Chicago handshake: the pairing of Old Style beer with the city’s divisive liquor, Malört. This combination isn’t difficult to find in the city. We closed out the night by ordering it at our hotel bar, since we had “welcome drink” tokens to use up. If you want more direction, it’s worth noting that a couple of fixtures from Eater’s beloved dive bar map aren’t far from Gene & Georgetti; consider Rossi’s Liquors or the Original Billy Goat Tavern.
Did you know? Eater has an app for iOS where you can find all of Chicago’s great local maps, handy lists like this food crawl, and even make your own maps to share with friends. Check it out, leave notes on your favorite restaurants, and make a reservation for your next great meal all in one place.
