7 Fantastic Food Experiences in Chicago

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Kate and Cailin

As soon as I decided to visit Chicago for a few days, I began planning meticulously. I started talking to everyone I knew who lived in Chicago or had visited there. I asked questions, took notes, even had a document in my Evernote compiling my information.

All this information…was about food.

I mean, yes, I wanted to do an architecture cruise and see Second City and have a meetup with my Chicago readers, but really, I came to Chicago for one primary reason — to eat!

Chicago is home to many unique food traditions, fantastic high-end restaurants, and its interesting ethnic mix means you’ve got great food from around the world. In short, there’s far more to Chicago’s food scene than deep dish pizza.

As a result, I ate quite well during my five days in the city and now consider Chicago one of my favorite food destinations in the United States. Here are seven of my favorite places to eat in the Windy City.

Chicago's Hour cocktail at Longman & Eagle

Upscale and Trendy Fare in Logan Square: Longman & Eagle

Longman & Eagle was recommended enthusiastically by a friend I made in Panajachel, Guatemala, and he swore up and down that their foie gras was one of the best things he’s ever eaten.

Longman & Eagle is an inn that doubles as a bar and restaurant. It oozes upscale hipster class, with a wide whiskey selection, craft cocktails, and a super-fancy menu.

I started off with one of their signature cocktails, the Chicago’s Hour: CH London Dry Gin, Jeppson’s Malort, Old Style, Grapefruit, Lemon. If you’re a gin drinker like me, go for it! Gin and lemon is one of my favorite combinations and they knocked it out of the park.

Beef Tartare at Longman and Eagle

Unfortunately, they were transitioning their menu and didn’t have the foie gras dish on the menu. But foie gras did accompany the beef tartare.

The full listed item: Beef Tartare, Foie Gras Torchon, Medjool Dates, Pluot, Mustard Greens, Buttered Challah, Truffle Gribiche. Very American in its complexity.

And delicious. I know raw meat isn’t everyone’s cup of tea, but when beef tartare is done well, it’s out of this world. There were so many levels of flavors in this dish!


Up next: Slagel Family Farms Bone Marrow, Bacon-Shallot Jam, Green Apple Kimchi, Pickled Garlic & Shallots, Parsley, Sourdough.

I love bone marrow — it’s a deep, rich kind of meat. I think this bone marrow had a LITTLE too much going on (one of the jams was not my jam, incidentally) but it was still glorious.

And to even things out, lest we eat nothing but meat, some salad!

Salad and Longman and Eagle

Not just a salad. Gem Lettuce Salad, Compressed Strawberries, Grilled Radicchio, Haricot Vert, Smoked Blue Cheese, Pistachios, Root Beer-Sherry Vinaigrette.

I still remember how pleasing the crunch of this salad was — I’ve never had such cold, firm, crispy lettuce in my life. And those compressed strawberries? Addicting.

Longman & Eagle was my favorite restaurant in Chicago, and if you’re looking for a special meal, this is my top recommendation. I am definitely returning on my next visit!

Beef Tartare, $18. Slagel Family Farms Bone Marrow, $15. Gem Lettuce Salad, $15. Chicago’s Hour cocktail, $10.

Duck Prosciutto Purple Pig

Cured Meats and Nose-to-Tail Eating: The Purple Pig

Longtime readers know I have a burning love for cured meats and nose-to-tail eating. As soon as I began researching, I stumbled across The Purple Pig, and it seemed like the perfect restaurant for me.

Cured meats. Small plates. Wine. Unusual pig parts. And purple is one of my favorite colors!

Crispy Pig's Ear Kale Purple Pig

Crispy pig’s ear on top of crispy kale with a fried egg on top. If ever there was a dish created for me, this would be it! I loved it. The pig’s ear was almost like fried clam strips, and the kale made me feel like I was being healthy. Ha.

Burratta with Artichokes Purple Pig

I also tried some whipped burratta with artichokes, and to be honest, while delicious, it was a bit of a letdown. Whipped burratta is like taking the finest steak and grinding it into hamburger. Burratta is meant to be sliced with a knife, oozing all over the place. Those artichokes were nice, though.

Many of The Purple Pig’s meats are cured in-house, so I sampled some duck prosciutto as well (pictured above the headline). Very, very good.

Also, the wine list here is outstanding. I couldn’t believe there was Croatian wine on the menu! Croatian wine is so rare to find it in US liquor stores, let alone restaurants! Of course, there was no way they had it by the glass, so I went with a Barbaresco from Piedmont.

The Purple Pig is in the Magnificent Mile area, so it’s very convenient if you’re hitting up Millennium Park or the Art Institute or doing an architecture cruise. Also, there are big communal tables in the bar area, which made me feel comfortable as a solo traveler.

Pig’s ear with crispy kale, pickled cherry peppers and fried egg, $9. Whipped burratta with artichokes, $9. Duck prosciutto, $10.

Charcuterie Publican

Super-Local Butchery: Publican Quality Meats

When talking to people about Chicago restaurants, Publican seemed to pop up in every conversation, yet nobody outright declared it his or her favorite.

Then I ended up at the small deli next door: Publican Quality Meats. Right away, I was impressed by the huge variety of local house-cured meats available for purchase, as well as lots of other homemade dishes.

Ribollita Publican

I was excited to see ribollita on the menu — it’s one of my favorite Tuscan dishes, a peasant soup made from stale bread and whatever leftover vegetables are available. Publican, of course, added meat. Rock on, butchers!

For my main dish, I decided to go with a charcuterie plate. Each day, there are five options from which to choose. I went for blood mortadella, an unusual kind of prosciutto (whose name I can’t recall, sadly), and headcheese. HEADCHEESE!

With bread, pickles, peppers, mustard, and a few other accoutrements, this made for an excellent lunch.

Ribollita, $4/7 for cup/bowl. Butcher’s cold charcuterie plate, two for $8, three for $13, five for $19.

Kimchi Pancake at Little Goat

Fancy Restaurant Meets Down-Home Diner: Little Goat Diner

The Girl and the Goat is one of Chicago’s most famous high-end restaurants, owned by Chef Stephanie Izard. But what about a more affordable restaurant? Enter the restaurant’s little sister, the Little Goat Diner!

I went for lunch but my eyes immediately went toward a breakfast specialty: Kimchee & Bacon & Eggs & Pancakes Asian Style Breakfast Tasty Thing. Easy decision!

It’s more of a pancake dish, very light, with layers of eggs and bacon in between the batter. The kimchee was not as plentiful as I would have liked (I am a kimchee fiend — you should have seen me in Korea!), but it was a fun and unusual dish, perfect for the atmosphere.

Smores Semifreddo

I rarely eat dessert or anything sweet, but I had to try one of the featured desserts — a s’mores semifreddo.

The dessert featured marshmallow ice cream, a homemade graham cracker-like cookie, marshmallow fluff charred by a blowtorch, and a chocolate sauce halfway between hot fudge and syrup.

I swore I would only have a few bites. For research purposes. Yeah, that flew out the window pretty quickly.

The Little Goat was a lot of fun and it’s a great place to get a high-end meal on a budget. And for solo travelers, the diner counter is perfect!

Kimchee & Bacon & Eggs & Pancakes Asian Style Breakfast Tasty Thing, $13. S’mores Semifreddo, $8.

Pizano's Pizza

Diving Into Chicago Pizza

There is so much to learn about Chicago pizza! After hearing rave reviews from my friends Cailin and Steph, I booked myself on the Original Chicago Pizza Tour. We visited four different pizzerias over the course of a few hours (Pizano’s, Flo & Santo’s, Pequod’s, and Piece, though the offerings change each day of the week).

I’m not going to lie — this was one tour where I felt a bit awkward to be a solo traveler. Perhaps because there was also a big family group and everyone else was paired up. I didn’t connect with anyone until fairly late in the tour.

(Side note: I was staying at my friend Wren’s apartment in Chicago, and she has a cat named Pizza and a pizza necklace. I was tempted to borrow her necklace for the tour — but yeah, showing up alone to a pizza tour while wearing a pizza necklace would have made things a million times more awkward! Where’s my champagne?)

Other than that, the tour was great. Our guide, Jonathan, was a curmudgeon and a half. The history and trivia was fascinating. The pizza was mostly awesome (except for Piece — turns out New Haven-style pizza is not my thing at all. How can you sleep at night without putting mozzarella on your pizza?!), and I was pleased to sample several kinds of Chicago pizza in a short period of time.

Cailin’s review and Steph’s review have a lot more details on the tour. GO HUNGRY, whatever you do!

Pequod's Pizza

Deep Dish in a Dive Bar: Pequod’s

I tried a few varieties of deep dish and my favorite overall was at Pequod’s, a tiny dive bar named after the ship in Moby Dick.

Deep dish is like a casserole — a very thick crust topped with lots of sauce, cheese, and toppings. Pepperoni is the most popular pizza topping in America, but sausage is the most popular topping in Chicago!

I think it was the sauce at Pequod’s that I loved — it had a wonderful, robust mix of spices, a big contrast to the lighter sauce on the deep dish at Pizano’s.

Pequod’s signature is layering mozzarella on the bottom of the crust, so it rises up and caramelizes (even burns) along the edges. Don’t complain that your pizza is burnt — this pizza is turnt!

Personal pan pizza, $7.45. Toppings are $0.50-1.20 extra.

Flo and Santo's Pizza

Polish-Italian Fusion Pizza: Flo & Santo’s

I’ve never been to an American city with a big Polish population before; the only time I’ve eaten in the very Polish Greenpoint neighborhood of Brooklyn, I had Thai food. (Wince.)

Between that and having never been to Poland (egregious travel oversight alert!), I’m not too familiar with Polish cuisine — but I really liked the fusion fare that I had here.

Flo & Santo’s brings together Chicago’s Polish and Italian dishes with a twist — putting them on Chicago South Side-style pizza! The Flo’s Polish pizza features kielbasa, sauerkraut, and applewood-smoked bacon. The Marco’s Italian Beef pizza is a take on the Chicago Italian beef sandwich and features shaved beef, giardiniera, caramelized onions, and fire-roasted tomatoes.

Both were fun takes on pizza, and I liked the Polish one best. Next time in Chicago I hope to sample the ravirogi, their ravioli-pierogi hybrid.

Flo’s Polish and Marco’s Italian Beef pizzas, $18/22/26 for medium/large/family. Ravirogi, $13.99.

Coalfire Pizza

My Favorite Chicago Pizza: Coalfire

Of course I try five different Chicago pizzerias and my favorite is the one run by two guys from Massachusetts! But in all seriousness, Coalfire has some of the best pizza I’ve had anywhere.

Coalfire is home to the only coal oven in Chicago and the pizzas cook super-fast!

Both Cailin and Steph declared Coalfire their favorite pizza in Chicago, and since Cailin was coming back to Chicago, we made a special trip.

We split a pepperoni and whipped ricotta pizza, and it was sensational. Amazing flavors. Super-thin crust. Neapolitan with an American twist. It’s definitely going on my list of favorite pizza places in the world.

If I lived in Chicago, I would eat here all the time!

Pepperoni and whipped ricotta pizza, $18.

The Wiener's Circle

Hot Dog with a Side of Trash Talk at The Wiener’s Circle

Ever since I first saw The Wiener’s Circle on Food Network, I’ve been dying to visit. It’s just a little hot dog stand that comes alive at night — the staff verbally abuse you as you order!


Cailin took a video of me placing my order and getting a side of sass.

And on the way out, the girl called me “Fake Nicole Ass Richie.” HA! (Cailin: “Oh! It’s because of your tan!”)

As for the food? Great hot dogs. Zero complaints.

Chicago Hot Dogs

The Chicago hot dog is very strict about its ingredients: mustard, relish, onions, tomato, a pickle, two sport peppers, and celery salt. Do not even think of skipping any of those ingredients — or worse, adding ketchup. Travesty!

Char dog, $3.20.

Kate and Cailin in Chicago

And If You’re Thirsty…

I didn’t spend much time exploring the bar scene in Chicago, but I did find two fabulous watering holes! (Didn’t get pics of either, but that’s a pic of the aftermath!)

It rained for most of my time in Chicago, but on the one sunny day, Cailin and I spent it the best way possible: drinking margaritas on the patio at Big Star in the very hipster Wicker Park! Margaritas, sunshine, chips and guacamole — that’s the recipe for a perfect afternoon.

The second was Hopleaf in Andersonville, where I had my meetup with my readers. It’s pretty far north but well worth the trip, thanks to a huge selection of Belgian beers and a warm atmosphere. If you’re into beer, this is a must-visit bar.

The Takeaway

I think my five days in Chicago was the best stretch of eating I’ve ever had in my life! (Believe me, I made up for it by going on a diet of salads and green juices for the next week.) Even if you’re a picky eater or not that into food, Chicago might make a foodie of you yet!


7 Kickass Places to Eat in Chicago

Essential Info: Prices are listed with the dishes above.

The Original Chicago Pizza Tour costs $60. It’s not a walking tour; you’re transported by bus. I paid for the tour myself.

I stayed with friends in Chicago but you can find hotels here.

Special thanks to my friend Wren for letting me crash at her gorgeous apartment during my time in Chicago. I’m totally moving in with you and Pizza, by the way. Is that cool with you? 😉

Have you been to Chicago? Where is your favorite place to eat?

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50 thoughts on “7 Fantastic Food Experiences in Chicago”

  1. Great list! Way to make me miss Chicago and make me really hungry in one go. Happy to see you tried Publican Quality Meats! Big Star and Hopleaf are two of my favorites as well, for drinks and food. I really miss the huge variety of amazing food in Chicago now that I live in France. Lyon is world-famous for its food, but I’d rather eat in Chicago any day. Thanks for sharing a slice of one of my favorite cities!

      1. Haha, well I certainly can’t knock the food or the culinary history in Lyon, but living here all the time does make me miss the international variety I was spoiled with in Chicago!

  2. You went to a pizza place ran by people from Massachusetts that serves flat crust pizza – THAT’S NOT CHICAGO STYLE PIZZA. I totally respect that some people don’t like deep dish and some people really like thin crust but seriously???????

    You got traditionally east coast-style pizza made by native east coast residents while you were in Chicago. And that’s fine, but DON’T call it Chicago Pizza. This is like ordering General Tso’s chicken from a Chinese place in Italy and calling it your favorite Italian restaurant. OMFG.

    1. I also have to say as a native Chicagoan that none of these restaurants represent Chicago-style fare. I’m glad you had a good time, but these are just overpriced hipster restaurants that are really anti-Chicago. Chicago has a culture of being an affordable city with a rich culture.

      You could have gone to Valois http://www.yelp.com/biz/valois-chicago where Obama frequents.

      Or the famous Chicago Diner http://www.veggiediner.com/ where you can get the best vegan/vegetarian food I’ve ever had.

      You could’ve tried Chicago style Italian beef. And for pizza places, you should’ve gone to Lou Malnati’s or Giordano’s.

      So many places that are Real Chicago Establishments. I’m so disappointed in this post. There’s nothing Chicago about any of this. Maybe you were trying to bring some new restaurants to the forefront or not talk about restaurants that have been talked about in other blogs, but these are just rich hipster restaurants in the gentrified parts of Chicago, and to me, that’s not what Chicago is about.

      1. Hi, Dana. Thanks for sharing. But do you really think that Pequod’s and The Wiener’s Circle are rich hipster restaurants? Quite the opposite, I found!

        Italian beef was a priority, but I just didn’t have the time by the end. I did try it in pizza form, though!

        As for pizza, not touching that one. 🙂 Every Chicagoan has very strong preferences! I think visiting five pizza places on a five-day trip was a good effort.

        1. As a Chicagoan, I think you went to a lot of VERY Chicago places. Just b/c Logan Square is hispter-eating central, for example, it’s still very indicative of the food scene that’s happening here now. And just b/c you went to some more mid-market or even upscale food places, that doesn’t make them any less authentic than Al’s Italian Beef (which I personally loathe–to each her own).

          Coalfire, for example is a great small place serving up really good pizza. And I couldn’t care less is the owners are originally from the East Coast or California–it’s simply good pie that’s being made on Grand Ave in the West Loop. Similarly, Pequod’s is, to my mind, a much more truly “Chicago” hole-in-the-wall place than Malnati’s (which is a suburban import for those wanting to get really picky) or Giordano’s. Not to be an anti-chain snob (but I am) but that’s like saying you can’t get an authentic American hamburger unless you go to McDonald’s.

          I also like your list b/c it’s always interesting to see one’s own city thru the eyes of someone else. It helps homers like us rediscover great things about our hometowns or remind us what to avoid the next time friends/relatives visit.

          Glad you had fun here.


          (PS-next time, you might want to put Spacca Napoli in Ravenswood on your list of places to try…)

      2. I seriously disagree. Pequod’s predates the hipster culture by a generation – I went there when I was a hip kid – 25 years ago. Purple Pig? The Banos clan has a great history in Chicago restauranting (sorry for the poor coinage…). Little Goat and Publican? Sure, they’re new and trendy…they’re also EFFING AWESOME, and in fact I steer people away from Girl and the Goat, telling them they’ll have a much more satisfying experience across the street. And DON’T get me started about Longman and Eagle…ANY establishment that has a full page of painlessly-priced “whiskies for drinking” is PERFECT in my book, hipster ‘hood be damned.

        I mean, come on…Adventurous Kate would have to move here and write a book rivaling War & Peace to do the Chi food scene justice….cut them some slack, Jack.

        1. Right, and Pizano’s started in the Malnati family so I don’t know why Dana would say she should go to Lou Malnati’s….I actually like Pizano’s better, though they are very similar!

    2. Hi, Dana — I went to Coalfire because two of my friends ADORED it and I wanted to try it for myself. And I never said it was Chicago-style pizza! Far from it. By the headline “Chicago pizza,” I meant pizza within the city limits of Chicago.

      I’m sorry this post made you so upset! Wow.

  3. I wish I saw this before I went to Chicago, because my butt would have DEFINITELY been on that pizza tour. When I went, my friends wanted plain deep dish pizza and I actually wasn’t as much of a fan as I thought I’d be. I guess I’m just a gal that likes some toppings in there. And also, I LOVE how much you love meat. You’ve got excellent taste.

  4. I LOVE FOOD POSTS!!!!!!!!!!!!!!!!!!!
    Ok, so “Very American in its complexity” is such a true descriptive! I find that this is one of the things I miss a lot about living in NYC – truly interesting, inventive ingredient and flavor combinations! Thankfully Moscow eateries are starting to get in on that game as well. And pizza with ricotta – yummmm. I had that on my first night in Bologna and it was spectacular. Why doesnt ALL pizza come with ricotta?

    1. It was actually an American friend who also once lived in Europe and has a European husband who told me that American food is so complex. I had never thought about it like that before!

      1. You know, I think it’s a recent phenomenon too. Like, of the last decade and a half or so? When every small town finally had a sushi spot, and then gastropubs started exploding, and then food trucks, and the way to carve out marketshare was to do fusion, or deconstruction, or molecular stuff, or just fun, new combos.

        Moscow is actually struggling with quality ‘ethnic’ food but young chefs are more confortable with reinvention and improvisations.

  5. woah!! Kate! This is delicious! Never been to Chicago, but hope on day I will.. I heard it is similar to NY..

    Unfortunately I am no longer able to eat like I used to and a lot of those wonderful things are off the menu for me.. pcos will do that for you.. At the moment I’m trying to stick to paleo-like diet..

  6. I loved the food in Chicago too although I couldn’t afford to do any fine dining while I was there. Loved the hotdogs at the weiners circle and pie at Hoosier Mama but my favourite meal was deep dish at Pizzeria Uno, open since the 1950s

  7. I love going to Chicago just to eat! Adam and I are from Milwaukee and would go to Chicago 3-4x a year, but we have been on the road full time since 2012…missing the food scene! You made me hungry=sucessful post

  8. Hi Kate,

    Awesome post – but you’ve now made me super hungry! I went to Chicago for the first and only time about 8 years ago now, so don’t have any recommendations on food places. I’d love to return (particularly in summer), It was Christmas and freezing cold when I went.

    It is such a cool city though and all these photos of food make me want to come back!

  9. One of the best lists I’ve read. I’ve lived in Chicago since 1958, so I know Chicago food. Except for The Weiner’s Circle (which I’ll give ya, cuz it’s a fun touristy thing to do…but there are 5 dozen better hot dog joints in the city…), you’re batting 1.000!!!

    Come back and try a couple of other delicacies:
    -Italian Beef (Mr. Beef on Orleans, Johnnies in Elmwood Park, Chickies are just a few)
    -Italian subs (Bari Market on West Grand)
    -Fried chicken with a frozen Negroni at Parson’s (or try Roost for our take on Nashville hot)
    -Spacca Napoli for a classic Neapolitan style pie
    -Mexican, Mexican, MEXICAN at any of the millions of cheap and great taquerias in town
    -Rib tips and links at Honey 1 BBQ on the South Side
    -great vegetarian fare at Green Zebra
    -and many, many more!

    1. YES!!! I totally agree with you (and while I’ve only be here 20 years I think collectively we can approve this list with some authority)!

      Spacca is dangerously located within walking distance of both my house+office so it’s a place we always recommend (and are very often found eating ourselves).

  10. The next time you visit Chicago you MUST try some of the little ethnic neighborhoods! Argyle Street has amazing pho and other Vietnamese food. Devon Avenue is like Little India, but also Pakistani, and there’s even a Georgian bakery! They told me it’s the only one in North America, and it’s awesome. The amazing food is what I miss most about living in Chicago – it’s just the best. However, my overall health has definitely improved by not living there!

    1. Next time, check out Chicago thin crust. There’s lots of hand thrown (the aforementioned Coalfire) and Neapolitan-style places, but to get the authentic experience, find a great thin crust place that cuts it into squares…Vito an Nicks at 84th and Pulaski is the standard-bearer, but there’s dozens of places in city and suburbs that do it this way. Awesome…and the stuff I grew up on (I never had a deep dish slice until I went away to the University of IL at Urbana!)

  11. Yuuuummmm. I love food posts like this because it makes me feel a lot better about how so many of my trips to different places are just about food. It’s one of the huge reasons why I travel and probably makes up half of my travel budget!

    The pizza looks delicious although I agree not putting mozzarella on your pizza is a travesty!

    I think I’d be too scared to visit the Weiner Circle. I love how you gave it back to them. I think I’d just be too nervous and just squeak ‘ok’. I wonder if anyone just rocks up there late at night without knowing what its about and gets the biggest shock?

  12. Everything looks seriously amazing. Chicago is my favorite city to eat in but I am a little biased because I’m from there. Living in Southern California now but missing all the good eat you can only get in the city.

  13. Pequod’s is one of my FAVORITE pizza places in Chicago. As is Piece. Each time my family visits from out of town, we go. Another classic favorite for Chicagoans is Portillo’s although they just sold the company for over a billion dollars ):

  14. That video is hilarious! I don’t think I’d have had the balls to go order a hot dog so go you woo!

    Chicago is my absolute all time favourite US city and you’ve definitely nailed down some of the best eateries. By the time I’d left Chicago I had eaten so much pizza that I’d basically turned in to a delicious deep dish.

    I recently posted my own guide to the windy city and this is bringing back all the memories. YUM!

  15. We recently went to Chicago also and loved it, but it certainly looks like you had the opportunity to try tons more food than we did! (although, I suppose that could be because we only had the chance to spend 48 hours there.) SO JEALOUS … Everything you tried looked so yummy! Loved the video of you at The Wiener’s Circle and you definitely gave us a new spot to visit next time we’re in the Windy City 🙂

  16. I’m heading to Chicago in September to start an internship, so I was excited to see this post! I can’t believe there’s a Pizza Tour. When I read that, I thought, “SHUT THE FRONT DOOR. I am so going!” Thanks for all of the recommendations!

  17. Bummer you only hit up the touristy/trendy spots and missed out on all of the great ethnic food Chicago has to offer. Ex: tamales in Pilsen!

  18. Ok, at the beginning of the post I saw THIN CRUST PIZZA and I thought you got mixed up! Then, as a middle-aged male, I must admit some of the dishes you showed I would never try. But then! You got to the glorious Chicago-Style Pizza! Nothing Better!!!
    Neat information! Thanks for sharing…Chicago is a neat place.

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