Where to Eat in Chicago: Iconic Eats & Must-Try Restaurants in the Windy City

This post may contain affiliate links wherein I earn a small commission if you purchase or subscribe to a product from one of my links (at no extra cost to you!). Read my full Privacy Policy here.

---

Chicago is a city with a food scene that is not for the faint of heart. When I planned our first trip to Chicago, the first thing I thought about was all the delicious food we were about to eat. The second thing was that I’d probably need to pack a large bottle of Tums.

Have no fear – just plan to do a lot of walking in the city to burn off all those calories!

Chicago’s Must-Try Foods

Chicago’s food landscape is filled with hearty dishes steeped in decades (and some times over a century’s worth) of history.

Whenever I visit a destination, I’m on the hunt to try the best foods it’s famous for. In the case of Chicago, there are so many dishes and food items with origins in the city! I’m talking massive deep dish pizzas and hearty Italian beef sandwiches. There’s also the signature Chicago dog and even more specialties like Garrett Popcorn and The Original Rainbow Cone.

And we can’t forget about Chicago’s favorite condiment, giardiniera – a spicy pickled assortment of peppers and veggies that’s worth putting on pizza, Italian beef sandwiches, and even the occasional Chicago dog.

All I can say is pack your stretchy pants.

Not sure where to start? Take a food tour!

Chicago Deep Dish Pizza

Deep dish pizza is often one of the top foods that comes to mind when thinking about what to eat in Chicago. I know it was for me!

This style of pizza is essentially a giant stuffed pie cooked in a deep, round pan. The crust is thick to hold up to all the cheese and toppings, with sauce going on top instead of directly onto the crust. It’s indulgent but each bite is worth the calories.

It’s widely accepted that Chicago-style deep dish pizza originated at Pizzeria Uno, with workers from said spot eventually moving on to other famous restaurants like Lou Malanti’s and Gino’s East. Regardless of where you have it (even though I have some favorites), it’s definitely a must-try dish when visiting Chicago.

Also Read: Best Deep Dish Pizza in Chicago: The Ultimate Deep Dish Showdown

The ambiance here is also very inviting – it feels like a true pizza place! This buzzing restaurant is complete with red checkered table cloths and booths covered in signatures and notes from patrons over the years.

In addition to a delicious pizza, we also experienced really great service here too, which elevated our visit.

Our pizza order: Gino’s Supreme with sausage plus giardiniera

Gino’s also has some really good side dishes, like their antipasti salad and artichoke dip. Because deep dish pizzas do take a while to cook (around 45 minutes), keep yourselves from getting hangry with a few apps.

We visited the Prudential Plaza/Millennium Park location and thought the restaurant had a great atmosphere. They also walk around and take “professional” photos that you can spend way too much on as souvenirs in a Giordano’s paper frame (but hey, memories right?).

Giordano’s might be famous for their cheese-stuffed pizzas, but their side dishes are even better!

I recommend starting with some appetizers while you wait for your pie to cook. A favorite: a heaping portion of calamari – nice and crispy with bits of lemon and peppers sprinkled in with the fried calamari.

We also really loved their Italian beef arancini, putting a twist on this Italian appetizer with a nod to a Chicago classic (Italian beef). Pro tip: skip the marinara dipping sauce for these in favor of the aus jus!

We visited the South Loop cafe location and while I can say it wasn’t my favorite spot for ambiance, their pizza is still a banger. They have a unique and special buttery crust and their pizzas are packed with toppings!

Our pizza order: The Malnati Chicago Classic – add mushrooms, green peppers & giardiniera

For starters here, I recommend the Malnati salad that has little crispy bits of fried salami and a sweeter dressing that will help balance out savory apps or a pizza. We also had the ravioli crisps, though I’d say those were just average.

Be sure to read through my Chicago Deep Dish Pizza Showdown to see how I ranked and rated these three pizza joints.

Italian Beef Sandwiches

Another Chicago favorite made TV famous by The Bear is the Italian beef sandwich. It may not be as well known as deep dish and Chicago dogs, but it deserves a place on your Chicago itinerary (and in your stomachs).

Thinly sliced roast beef is simmered in a sauce with seasonings and then served on a roll topped with your choice of hot or sweet peppers (or both, which I personally recommend). You can get it dry (boring), with a scoop of “gravy” or aus jus (better), or dipped (best!) – sometimes double dipped if you live on the edge.

It’s a messy sandwich but pure salty and savory heaven.

We’ve eaten at five different spots for Italian beef in Chicago so far, but I’m listing my top three here. If you want to read about all the others, check out my post ranking them against each other!

Also Read: Hot, Sweet & Dipped: Ranking the Best Italian Beef Sandwiches in Chicago

As with all of our Italian beefs we tried in the city, we ordered ours at Portillo’s with hot (giardiniera) & sweet peppers. Both types provide a balance of flavors in addition to different textures. Their giardiniera was nice and spicy too – an unexpected kick in the best way.

Portillo’s slow roasts their beef for four hours and the meat drippings are turned into a delicious gravy. We got our sandwich dipped (as we did at every spot) because I wanted to taste the full effect of that gravy!

I think that a having a slightly soggy sandwich is just a part of the whole experience – I highly recommend it. Just know that you’re going to use a lot of napkins.

This is an all around solid Italian beef choice in Chicago!

What makes Johnnie’s the best are the flavors of the meat and gravy. After consuming five Italian beefs prior to this one, I knew immediately when I bit into it that it was “the one.” This sandwich is loaded with beef and tons of sweet peppers and giardiniera!

A word of warning though: Johnnie’s is also the messiest (meaning if you get your sando dipped, expect it to start falling apart about halfway through). Again, I think that’s all part of the experience but you may want to pack some wet naps for this one.

The beef is also sliced more thickly and the sweet peppers are larger too. Ciccio’s sandwiches also come with side of roasted potatoes, which are phenomenal. I could eat a whole tin of just their potatoes!

And let me tell you about the aus jus – dark, rich, and with some of the best flavors out of all of the Italian beef gravies we’ve had thus far. I wish we had gotten a larger sandwich because it was just so enjoyable.

Chef Ciccio also makes a mean meatball sub (as the name of their spot suggests – beef AND balls). Meatball subs are one of my favorite sandwiches. I love the tangy tomato sauce and melted cheese smothering a tasty meatball.

Chef Ciccio is located at Navy Pier which can be buzzing with people at times, but I feel like this one is definitely “underrated” in terms of best Italian beefs in Chicago. Get it.

Chicago Dogs

If deep dish pizza and Italian beef don’t scream Chicago enough for you, enter the Chicago dog – the city’s famous, affordable handheld meal with a unique array of toppings.

Identified by its “drag-it-through-the-garden style,” Chicago dogs are my favorite way to eat a hot dog!

Firstly, mustard is the star here – ketchup is not allowed. Then, pickle spears, fresh sliced tomatoes, diced white onions, unnaturally-colored green dill relish, and pickled sport peppers (my personal favorite component) are stuffed into a poppyseed bun with the dog and topped with a dash of celery salt. It’s colorful and refreshing!

Most places in Chicago will use the Vienna Beef brand of hot dogs, but there are a few who don’t (that might be sacrilege to native Chicagoans). Look for the signature yellow, blue & red “V” logo to be sure!

Here are some of my recommended spots for a good dog.

I highly recommend grabbing a cider or a beer and a Chicago dog and just people watch and/or watch all the boats float by on the river while being under the lights of the city skyscrapers themselves. It’s a vibe.

In terms of their Chicago dog, I can tell you it’s definitely the prettiest dog we’ve eaten in Chicago! Our bun was a little dry though, which is why it wasn’t my top favorite. However, it’s still a solid choice if you’re craving one of the Windy City’s finest meals.

Of course, you’ve gotta get a Chicago dog when you’re at Wrigley! I had to DIY our dog – you purchase a box with a plain hot dog and head over to the toppings bar to add as much or little of everything as you like. At first, I was against this but in the end, I liked having the control over how much I could fit into my bun.

Clearly (from the below) I like extra mustard (and using lots of napkins) and the best part was I could put as many sport peppers as I could humanly fit into my bun. I actually think the perfect amount of sport peppers is six – three on each side of the dog.

The bun here was probably the most moist of all the Chicago dog buns we had and of course, they use a flavorful Vienna Beef dog.

I would say the atmosphere may have contributed to my enjoyment of this Chicago dog as well, but overall I rank it at a 9/10 – even considering the fact I had to make it myself.

Portillo’s has such a cool vibe when you walk in, decorated to seem like you are perusing an outdoor neighborhood in the era of 1930s Prohibition. It’s such a fun and bustling spot to enjoy some Chicago classics!

There are many locations of Portillo’s in the greater Chicago area, but two in the more immediate downtown area. We visited Portillo’s & Barnelli’s on Ontario which is more convenient for those staying in the Northern areas of the city, with Canal & Taylor closer to the South Loop.

Best Donuts in Chicago

Chicagoland must also equal Donutland because there are a ton of donut shops in town! Naturally, I want to visit them all to see who really has the best donuts in Chicago. Here are the spots I’ve been to so far and what I’d recommend at each.

Their raspberry-filled croissant donut is easily my favorite donut out of all the donuts we’ve tried in Chicago! Covered in sugar and stuffed with raspberry filling, sinking my teeth through the layers of croissant dough was just pure heaven.

Another popular donut here is the Biscoff Pocket, which you obviously have to try if you are a Biscoff cookie fan! The creamy cookie butter in the middle will definitely satisfy that cookie craving. Warning – it is very sweet, so I do recommend sharing this one.

The old fashioned donuts were both a little on the dry side for my liking but the ugly duckling of them all – the cherry fritter, was the best in flavor! I’d definitely go back for more of the fritters, which they also make an apple variety of as well.

Firecakes is a small donut shop (at least for the River North location) with no seating, so it’s essentially a take-out only spot. Grab some donuts here on a walk after visiting Portillo’s!

My personal favorite, however, is Raspberry Bullseye (which I think might be seasonal and only available at certain locations). If you like jelly donuts like myself, their tangy raspberry filling is delish and the crumb-style donut was light and airy.

We visited the Wrigleyville location before a Cubs game to have our breakfast of champs but there are multiple locations all throughout the city.

Other Iconic Chicago Eats

There really is such a long list of things to eat when visiting Chicago! Aside from all the food-coma inducing dishes I’ve already mentioned, here are some other must-try foodie spots when in the city.

My recommendation: go for the The OG, served with five signature flavors (in slices, no less) of chocolate, strawberry, Palmer house, pistachio almond, and orange sherbet. This may sound like a weird combination of ice cream flavors to have all at once, but I was shocked at how well they all ate together.

There are dozens of locations in the Greater Chicago area, but the main spots to visit in the city are at Navy Pier (where we went – only open seasonally), Magnificent Mile (right next door to Gino’s East), and one of their newest locations near Millennium Park right next door to another Chicago institution, Garrett Popcorn.

My favorites: the Midwest Fried Chicken, fish and chips (that beat Bobby Flay), and a special uovo raviolo they had at the time we visited.

Also, don’t skip the Parker House Rolls! They are so soft and fluffy served with a light and salty whipped butter.

The menu at The Dearborn does change seasonally but you can expect some favorites to remain consistent (like the fish and chips, rolls, and Midwest Fried Chicken). On my list of things to try here next time: the Burger Wellington and one of their tavern-style pizzas.

The biggest fan favorite at Garrett is The Mix – a mix between their CaramelCrisp and CheeseCorn for those who like to enjoy flavors of savory and sweet together. We of course tried this for research purposes, but I personally preferred them on their own (with the CaramelCrisp being my favorite).

Pro tip: if you don’t plan on eating your popcorn same day, you’ll definitely want to get it in a sealed container and/or pack a Ziploc bag because the popcorn will go stale (as popcorn does) if left to the elements.

Grab a bag of this city’s famous popcorn at the Michigan Ave location and take it to go while you wander around Millenium Park.

Wish List Chicago Eats

There are so many more iconic Chicago foods I need to try on our next trip! These are some other Chicago-famous eats that I’m itching to try soon:

• Palmer House Brownie: The brownie was created right here in Chicago at the Palmer House Hotel in the late 1800s! Visit The Lockwood restaurant at the hotel to try this famous dessert, or the Lockwood Express for a grab n’ go brownie.
• Maxwell Street Polish: Another Windy City famous dog – this is a hearty polish dog served with grilled onions, mustard, and sport peppers. Get this at Jim’s Original (the OG spot), Portillo’s or other hot dog spots in the city like Devil Dawg’s or Chicago’s Dog House.
• Jibarito: Drawing from the city’s Puerto Rican community, this unique sandwich is made with flattened, fried plantains instead of bread and filled with protein, cheese, lettuce, tomato, and mayo or aioli. Some popular spots to try this are Papa’s Cache Sabroso, Jibaritos y Mas or The Jibarito Stop if staying downtown.
• Chicken Vesuvio: Another Italian-American creation born in Chicago, this one-pan dish generally consists of bone-in chicken and potato wedges roasted with garlic, white wine, and herbs, finished with peas and lemon juice. Where I’ll be trying this: Harry Caray’s Italian Steakhouse.
• Tavern-style pizza: A thin crust pizza cut in squares. My love Gino’s East serves tavern-style pizza – I’d personally start there if in downtown, but there are a ton of other spots in the city serving this type of pizza.

Wish List Restaurants

As with all of my food guides, I typically include a list of restaurants I’d love to eat at in the future – and let me tell you, the list for Chicago is about a mile long. Here are some of my tops:

• Girl & the Goat: Top Chef Stephanie Izzard’s spot in the West Loop featuring an inventive menu.
• Monteverde: Another Top Chef highlight in the West Loop, Sarah Grueneberg’s Italian rooted menu looks amazing.
• The Duck Inn: For a Chicago dog made with beef and duck fat and their take on an Italian beef with shaved prime rib.
• Pequod’s: As one of the most highly-recommended deep dish spots in the city, it has eluded me. I think their pizza is more of a thick pan-style pizza though. Nonetheless, its on my bucket list.
• Billy Goat Tavern: I’ll follow in the steps of Anthony Bourdain, and duck under the streets of Chicago one of these days for a greasy double “cheezborger.”

---

What are you adding to your Chicago list of must-eats? Is there anything you think I should try that I missed here?

Read Next:

• Best Deep Dish Pizza in Chicago: The Ultimate Deep Dish Showdown
• Hot, Sweet & Dipped: Ranking the Best Italian Beef Sandwiches in Chicago
• Searching for the Best Chicago Dog in Chicago: A 5-Dog Taste Test