There are approximately a million great food options in Chicago (so I am 100% sure I am missing many great ones), but I still thought I would share our favorites.
I like to stick to the delicious, unfussy classics to get to know a city, so I've divided my picks into the following iconic Chicago categories for your checklist:
+ Deep dish pizza
+ Chicago style hot dogs
+ Old school Italian
+ Nostalgic big city deli
+ Hearty midwest breakfast
DEEP DISH PIZZA
Everyone you ask has an opinion on the best slice, but mine is that Gino's East serves a great classic Chicago deep dish pizza with excellent ambience! We got this recommendation from quite a few friends and it didn't disappoint. The crust is something out of this world. I am not even sure I can describe it. Thick, but pillowy soft? Delicious, is what it is. It was hard to eat more than one slice though; this is a hearty stick-to-your ribs meal, particularly if you load it with meat like my husband and dad did. Kit and I stuck to the good stuff- cheese, cheese, and more cheese!
I also enjoyed the colorful location (writing everywhere- walls, booths, counters!) and since the pizza takes about 45 minutes to cook, there is plenty of time for appetizers and drinks. They also have reallyyyy great cookies if you save room.
CHICAGO STYLE HOT DOGS & OLD SCHOOL ITALIAN
Portillos is now a chain across the midwest, but for good reason. My aunt served us their Italian beef and got us hooked. Their eat-in downtown Chicago location was brimming with different food options, including classic Italian and Chicago style hot dogs. It was busy, casual, and kitschy. A little chaotic, but great food and something for everyone.
NOSTALGIC BIG CITY DELI
Eleven City Diner was one of my favorite Chicago finds. Retro soda fountain, candy shop, and delicious eatery. The decor inside was impeccable and it honestly did transport me back in time a bit. I got a vanilla coke (mixed like the old days) and classic soup and grilled cheese.
This is another eatery that is sure to please a group, as there were a plethora of food options. I had to get a sundae to end the meal, because how can you not somewhere like this?
HEARTY MIDWEST BREAKFAST
Wildberry Cafe is SERIOUSLY the best breakfast place in Chicago, and might (dare I say?) have the best pancakes I've ever had.
If you're craving pancakes, skillets, or a classic breakfast plate, this is where to go. The signature 'berry bliss' pancake (pictured above) is my top pick. If you're in Chicago for longer than just a weekend, I recommend saving this location for a weekday breakfast so it isn't quite as crowded.
And there you have it, a few classic restaurants to get your trip planning started. Chicago is a vibrant (and delicious) place to visit so I am sure you will love it.
And if you already do LOVE Chicago, I would like to hear your favorite eats for future visits, so comment away!