10 Things You Must Eat in Chicago

Oct 24, 2012 by

Okay, so Chicago is a food town.  Big time.  You can get a fantastic version of pretty much any kind of food on the planet somewhere in this city, if you know where to look or whom to ask.  I’d venture to say that, on the whole, the food here is more consistently amazing than anywhere else I’ve been in the USA, even NYC or especially LA.  What I mean by that is, if you walk in a restaurant in Chicago that you know nothing about, you are still fairly likely to end up eating a delicious meal; it’s hard to get a dud.  That is not the case in other big cities, but here, culinary mediocrity does not last long.  We’ll put up with sub-par transportation systems and politicians for decades, but “meh” food is not an option.

So, in a gustatory landscape so vast and varied, how is a person to ferret out the best, the most transcendent of the dishes on offer?

See below.

These are the things I ate with extreme frequency during the years I lived in Chicago, and what I make it my business to consume when I’m back to visit (like this week).  You cannot go wrong with any of these restaurants, so even if the dish listed below doesn’t wholly appeal to you, I can say with all confidence that something on the menu will catch your eye.  You can trust that these restaurants are among the finest in this fine city, and all have my utmost recommendation.  These are the places I’d take you to eat if you were with me, and what I’d recommend you order.

A few caveats about the list:

  • There are no desserts on this list — that will be its own list, for another time.  I am serious about desserts.
  • I am not going to tell you about Hot Doug’s or Kuma’s Corner.  There are reasons for this.  First, if you know anyone in Chicago, they probably already told you to eat there.  Second, I don’t eat meat in restaurants unless I know where it came from, so these were never two of my favorite places, being as they are both meat palaces.  I will offer this in the way of suggestion: if you want a fantastic Chicago-style veggie dog, head to Revolution Brewpub.  If you want some amazing veggie burger goodness, order the veggie mini burgers with chile-cumin dressing at Morseland.  Also, I’m sure someone already told you about Garrett Popcorn.  I won’t insult your intelligence.
  • There is a price cap on this list.  Chicago is home to some of the most fabulous fine-dining establishments in the country and some of the world’s most rockstar chefs, and everything you’ll eat at Tru, or The Girl and the Goat, or The Publican will be a flavor sensation to last a lifetime.  But those places aren’t usually on my list of destinations when I’m visiting for a short time on a limited budget.  Check them out if you want some fancy, spectacular eating.  But the dishes and restos on this here list are more moderately priced, and you won’t need a reservation to eat them.
  • Finally, Chicago is home of perfectly prepared ethnic food from all over the world, usually created by people who were born and raised in those countries.  But for the purposes of this list, I have tried to include dishes that are unique to Chicago, dishes I haven’t seen on the menu in other places, that I can’t get anywhere else.  For example, many places here make great pad thai, but you can generally find pad thai anywhere, so that wouldn’t make this particular list.  Quickly, if you want ethnic recommendations, mine are: sushi at Wakamono, Indian/Nepalese at Cumin or Essence of India, Greek at The Greek Islands, Cuban at 90 Miles Cuban Cafe, and mouth-watering Ethiopian at Demera.

So, with no more ado…

(in no particular order)

Duck Fat Fries from The Bristol

Duck fat fries at The Bristol

The dish: Be honest – does that name not make you want to stop whatever you’re doing right now and make your way to Bucktown?  Miles and I used to live around the corner from The Bristol, and we took any occasion we could to “wind up” there for everything from a few drinks and appetizers to a full-on birthday dinner with 20 friends.  But always, always, we indulged in the perfectly crispy, impeccably seasoned with herbs and sprinkled with cheese, “served with house ketchup and garlic ailoi” duck fat fries.  These are the stuff that dreams are made of.

The price: $7.  Note: This is probably the “fanciest” restaurant on the list, but it’s by no means hoity-toity.  You can make a reservation, and I’d recommend it on the weekend, but it’s not imperative and can be done the day of if you like.  Also, dinner here doesn’t have to break the bank.

The place:  The Bristol just might be my favorite restaurant in Chicago; it was actually hard to pick which mouth-watering treat to include on this list.  Since all of the ingredients are local and organic, including the meat, this is one of the few restaurants in Chicago where the entire menu is open to me (and the menu is also constantly, seasonally changing).  Also, the drinks here are among the best I have had anywhere, in my entire life.  Someday I’ll do a list of the best Chicago places to get crafted cocktails, but for right now, let’s just say The Bristol’s Dark and Stormy will be at the top of it.

What else is on the menu: There’s not a bad option here, and the menu and specials change so much that you will probably find something amazing to eat that I don’t even know about.  For sure-fire starters, order the savory monkey bread with dill butter and sea salt, or the apple salad with manchego cheese and roasted hazelnuts (which I have been known to order as an entrée, myself).


Pequod’s Pineapple Deep-Dish Pizza

Deep Dish at Pequod’s Pizza

The dish:  It’s Chicago pizza — you know what it is.  Or, you think you do.  A pie-shaped casserole of cheese, sauce, and fillings.  Touristy at worst and common at best, you might erroneously believe you’ve done Chicago pizza and you can skip this item.  But until you’ve eaten at Pequod’s, you don’t know jack.  Every person in Chicago has a favorite pizza place they’ll defend as vigilantly as their religion or baseball team, and Pequod’s is mine.  I had a different opinion before I started dating Miles, but after he took me to Pequod’s twice, I had to concede and shift my allegiance.  The sauce is an exact balance of sweet and spicy, the cheese is pitch-perfect and not overbearing, and the crust is what really makes the whole thing zing.  Pequod’s bakes their pizzas in the same pans they’ve been slowly seasoning for something like 30 years, and the crust actually bubbles up and over the lip of the thing and caramelizes.  You read that right — caramelized pizza dough.  It’s better than you can imagine.

The price: Varies (see menu here)

The place:  Pequod’s feels like a clean dive bar.  I mean, that’s essentially what it is.  The place is pretty big, but it still fills up almost every night, and the deep-dish pizzas take 45 minutes to cook.  Luckily, if you go with a plan in mind, you can actually put in your order while you’re waiting for a table, or even call ahead and pre-order so the pizza’s ready when you arrive.  I like that about the place.  Pro tip: Pequod’s is much, much less crowded at lunch, and they feature a truly spectacular lunch special of a personal-sized pizza (which is still twice as much as I can eat) and a beer or drink for something like $5.

What else is on the menu:  My favorite pizza topping is pineapple, which makes most people almost offended when they hear it.  Any topping you choose will result in the perfect Chicago-style pizza, so never fear.  There’s a whole bar-food-type appetizer menu, but I’d save your appetite for the main event.


Seitan Vegetarian Gyros

Veggie Gyros at Chicago Diner

The dish:  This is listed as the “fan favorite” on the menu, and I have to believe I had something to do with that.  I have eaten so, so many of these, due in part to the fact that I used to live across the street from the Diner, but also because they are just so amazingly, semi-inexplicably delicious in every way.  “Pita bread with sliced seitan, chopped onions, tomatoes & lettuce, with vegan tzatziki sauce,” might not sound like a miracle, but a dish that has all of the flavor of this Greek favorite with none of the discomfort or meat sweats is highly to be praised.  I still, simply, can’t get enough.

The price: $9.50

The place: “Meat free since ’83” is the slogan of the best veggie-centric eating establishment in Chicago.  This is the place where vegetarians can congregate to eat meatless versions of anything they might miss from their carnivore days — a Reuben sandwich, say, or Chicken Parmesan.  The vibe is achingly hip, in a fantastic way, and you can get so comfortable here, eating great food and chatting with friends, that entire afternoons slip away in the blink of an eye.  In the summer, I really recommend sitting in the patio garden out back.  The music is always spot-on and I have fallen in love with every member of the waitstaff separately and completely.

What else is on the menu:  Any kind of vegetarian fare you can imagine, nearly all of which can be made vegan.  The eggplant parmesan is great, as are the appetizer “wingz” (made buffalo or BBQ).  Occasionally, there one of the specials will be fried ravioli with dipping sauce, and these are always worth ordering.  Also, the milkshakes are expensive, but positively transcendental.


Plantain Mole Enchiladas from El Nuevo

Plantain Mole Enchiladas at El Nuevo Mexicano

The dish: I don’t have a very refined palate for Mexican food – to me it’s either good or it’s not, and I can’t begin to tell you why a dish succeeds or fails.  So you’ll just have to trust my un-nuanced pronouncement that these enchiladas are plain heavenly.  An unfailingly perfect combination of sweet, spicy, and smoky flavors, I have searched in vain for any enchiladas anywhere else as delightful as these “three soft corn tortillas filled with fried plantain bananas and simmered in homemade poblano mole,” served with Spanish rice, refried beans, and a small salad.  It’s extremely hard to find the perfect mole sauce, and El Nuevo is the standard by which I measure all others.  You’ll just have to try this dish for yourself to understand.

The price: $12

The place:  El Nuevo may be my best-kept secret on the list; when I was reviewing this blog project with Chicago friends, none of them had ever heard of the place.  I probably wouldn’t know about it either, except that I used to date a guy who lived about a block away, and we started many evenings here and ended them at the bar a few doors down.  The ambiance is definitely way more upscale than a taqueria, but it’s not stuffy.  Great for a date, clean and intimate and easy to get to, with friendly staff and a well-stocked bar.  Pro tip: this isn’t a very touristy or businessy area of Chicago, so if you pop in for lunch on a weekday, you’ll have the place virtually to yourself, and the waitstaff will give you their undivided, doting attention.

What else is on the menu:  The side of cinnamon yams is great, as is the ceviche.  You can order chicken dishes made with free-range, hormone-free birds.  There are plenty of vegetarian options.  There is also a respectable selection of tequilas and margaritas, and in colder months, you must indulge in a cup of the rich, spicy Mexican hot chocolate (if you don’t see it on the menu, just ask for it).


Phuket Noodles with Tofu

Phuket Noodles at Joy’s Noodles & Rice

The dish:  I have eaten a lot of noodles in a lot of places, but I have only seen Phuket Noodles at Joy’s: “Stir-fried spinach noodles with curry, napa cabbage, onion, carrot, bean sprout and egg.”  Curried and intensely flavorful, they pair perfectly with all of the meat options proffered: I enjoy the tofu or shrimp, but Ashley swears by the beef.  Phuket noodles are not very spicy, unless you request extra heat.  Pro tip: these noodles are even better cold!

The price: $9

The place:  Joy’s Noodles is an open, bustling, cheery BYOB Thai joint in Lakeview, with a seemingly inexhaustible staff.  In warmer months, there is outside seating both in front and in back.  I used to live mere blocks away, and on cold winter weekends, my roommates Jane and Ashley and I would order obscene quantities of food from Joy’s, have it delivered, and proceed to sit around eating noodles, dissecting our lives and feelings, and watching crap TV for a full 48 hours.  It was an almost holy winter ritual, one that saved our sanity more than a few times.  There are plenty of Thai places in Chicago, there are probably hundreds, but there is only one Joy’s.

What else is on the menu:  All your Thai faves are rendered deliciously at Joy’s.  I wholly love the steamed shumai (dumplings) appetizer, and I also think the thai iced coffee is perfection in a glass.


Chilaquiles at Kitsch’n

The dish:  One of the very first things I ate in Chicago (thanks to my good friend Heather), and still one of my favorite breakfasts on the planet.  Other places in the city have this dish on their brunch menu, but nowhere else even comes close.  “A spicy mix of eggs, fried tortillas, smoky chipotle salsa and pepperjack cheese; served with applewood smoked bacon and Texas toast.”  I always add avocado and get the bacon on the side to give to someone else at the table.  So good, I once ate this every Saturday morning for six weeks in a row.

The price:  $8.99 (+$1.50 for avocado)

The place:  Kitsch’n is one of the coolest spots in Chicago, and at prime brunch time there is usually a line to go with that reputation.  Regardless, it’s so much fun, so laid-back and cool and the waitstaff and food are so amazing, that I have brought nearly every person who ever visited me in Chicago to eat here.  You won’t regret it.

What else is on the menu:  The coffee and brunch drinks are excellent here, as are the Coconut-Crusted French Toast and the curly fries.  If you really like Twinkies and you have someone to share with, try the Twinkie Tiramisu for dessert.


Mozzarella Thicks at Leona’s

The dish:  You can find any number of variations on the traditional “cheese stick” everywhere from the frozen foods section of your grocery store, to the diviest dive bar.  I have always enjoyed them, but never really thought of them as really a “dish,” much less the kind of dish that could ever be elevated to an art form.  But lo, when I moved to Chicago some years ago, one of the first boys I dated told me that the mozzarella thicks at Leona’s would change my life, and so they did.  He lied about pretty much everything he ever said to me, but for this one bit of delicious truth I will always be thankful.  Hot and cheesy, as expected, these gigantic pieces of “mozzarella cut thick from the brick and fried” are slightly sweet, bigger than life, and absolutely transcendental.  They are sold individually due to their size, and they’ll absolutely ruin your dinner, so proceed with caution.

The price: $1.50 each

The place:  Leona’s is a Chicagoland institution.  The menu is encyclopedic, and the food is reliably great.  The first Leona’s was founded over 60 years ago, and it’s still a (sprawling) family business — there are drawings and bios of key family members and other employees inside the very long menu.  Leona’s is open late and it delivers.  There is truly something here for everyone.

What else is on the menu:  As I said, Leona’s has something for everyone.  Their pizzas and pastas are filling and flavorful, the menu includes a veritable buffet of lasagna options, and their vegetarian burger is among the biggest, best, and most customizable in the city.


A Wreck Sandwich from Potbelly Sandwich Works

A Sandwich at Potbelly Sandwich Shop.

The dish:  A sandwich, really, Chelsea?  And from a chain, no less?  You know what — yes.  I have eaten A LOT of Potbelly sandwiches in my time, and they are consistently delicious.  I have also spent a lot of time singing the praises of these sandwiches and mentally slapping sandwiches from other chains out of the hands of less-enlightened eaters, so yes.  This is something you must eat in Chicago.  The bread is perfectly toasty and crusty without being too hard and crunchy, the cheese is exactingly melted, the topping options are fresh and varied, and the real kicker is the special no-extra-charge hot peppers that top it off.  My favorite is the Mushroom Melt with extra toppings, but there are plenty to choose from and all are great.  Pro Tip: for a minimal up-charge, you can add any salad topping to a sandwich, like cucumbers, artichoke hearts, or blue cheese.  Just ask.

The price: Varies (see menu here)

The place:  Potbelly now has locations across the US, but it was started in Chicago (as an antique shop!) and Chicago is still the city with the most ubiquitous Potbelly presence.  The vibe is relaxed and comfy, not sterile and hurried, even though it is a chain.  At peak times, there is live music (usually one guy with an acoustic guitar) which actually adds to the chill atmosphere, and can make a nice change from your hectic workday if you’re popping in for a lunch fix.  If you are grabbing lunch somewhere really busy, like downtown, you can actually call in your order ahead of time and pick it up at the cash register.

What else is on the menu:  Potbelly’s cookies are delicious, and the milkshakes (served with a tiny cookie on the straw) are legendary for good reason.  I have heard the salads are yummy, but cannot personally confirm this.


Quesadilla at Lula Café

Mushroom, Ricotta, and Caramelized Squash Quesadilla at Lula Café

The dish:  The portion size is exactly right for lunch, sharing, or leaving room to taste some other foods on offer.  These quesadillas are exceptionally crafted in every way. “Hen of the woods mushrooms, ricotta, and caramelized chayote squash” on two perfectly-cooked tortillas.  This dish was recently re-imagined to include the squash, and I do miss the smoky red chili sauce that used to accompany it.  But, I have to admit that the bright green sauce that it’s served with now is also a pitch-perfect compliment.

The price: $8

The place:  Lula Café is one of my most beloved Chicago dining spots, and I am not alone in this.  Again, it’s one of the first places I ever ate in the Great White City (again, thanks to Heather), and I continue to be infatuated with it, even after they’ve expanded it and it no longer feels like my cramped, cozy secret.  Lula is a superior, bright brunch/lunch establishment by day that transforms magically into a twinkly, romantic dinner location by night.  Everything is fresh, local, seasonal, and exquisitely prepared.  You absolutely cannot go wrong with Lula.

What else is on the menu:  Any of their French Toast variations will blow your mind, as will the chilled peanut satay noodles, and the tineka spiced peanut butter sandwich is like nothing you’ve ever had.  Plenty of options for meat eaters, too.


Blueberry and Pumpkin with Cinnamon Glaze Muffins from Lovely

Muffins from Lovely: A Bake Shop

The dish:  It’s not  just a muffin, it’s a perfect muffin.  Exactly halfway between dry and greasy, exactly halfway between stale and spongy, exactly halfway between bread and cake.  It’s also the perfect size, and comes in a variety of ever-changing scrumptious flavors.  Served with the Intelligentsia coffee that Lovely does so well, these make the perfect light breakfast or mid-afternoon snack.  A dish doesn’t have to be complex to be a must-have.  Lovely: A Bake Shop takes the humble muffin and elevates it to the sublime.

The price: $1.45 each

The place:  Lovely is a thoroughly cute (borderline precocious really) airy retro-chic coffee shop and bakery.  They do make a few “meal-type” items every day, but really, it’s all about the baked goods here.  It’s a great place to work or read, though it can get crowded and loud on the weekend.  There is a lovely courtyard for outdoor seating in the less inclement months of the Chicago year.

What else is on the menu:  All the bakery items are delish, but I really recommend the cupcakes for their perfect size and price in addition to taste.  $1.75 for a cupcake that is, size-wise, like what you’d make at home, as opposed to $6 for a half-cake you’ll make yourself sick on.  The coffee drinks are also superb.

There you have it. Bon appetite!

My suggestion is to start with this list, compiled by me, a professional fan of food AND lists, and make your way from there.   All of these dining establishments are reasonably priced, have a great ambiance, and employ friendly, efficient servers.

What did I forget?  Leave your forgotten faves in the comments, Chicago!


  1. Danielle

    I can confirm Potbelly salads are delicious.
    Also, I wake up at night craving the Village Vegetarian sandwich from Costello’s, cinnamon rolls from Ann Sather (just the ones that are absolutely fresh out of the oven), and Ebelskivers (tiny pancakes stuffed with peanut butter, jelly, or chocolate) from the Latitude brunch bar. I also once ate an entire pound of Costello’s pasta salad as a hangover cure (it worked swimmingly.)
    Ugh, I miss Joy’s too. Also – and I say this with extreme guilt – Al’s Beef does these amazing Buffalo Bleu fries to go (love ’em) . . .

  2. Meaghan

    I know these type of lists are supposed to be provocative and stimulate discussion, but Potbelly!? You would have someone visit Chicago and eat a slightly better version of a Subway sandwich? No. Go see Mike at Piatto Pronto. http://www.piattoprontodeli.com/

    Chilaquiles at Kitsch’n is spot on though.

    • Ken

      I so agree. What the hell on the Potbelly! I mean I like it but really?

  3. Jean

    Love the blog! You are so right about great food in Chicago! Remember when we trekked all over Chicago to eat eight different ethinc meals in ten days! And, yes, they were all delicious!

  4. Jason

    I agree with everything except Potbelly. Really?

  5. Alex

    I’m sorry, but…Potbelly? I don’t care if it was started in Chicago. I can (and do) eat Potbelly subs regularly up and down the east coast when I need a quick and cheap lunch. If I’m visiting a city with some unique food cultures, or restaurant dishes, that I can’t find elsewhere then why would I chose to get a sub from a national fast food chain, even if it is a very good fast food sub?

Leave a Reply

Your email address will not be published. Required fields are marked *