Where should we eat in Chicago?

My friend Ginger and I are headed to Chicagoย soon for a fun weekend trip filled with sightseeing, shopping, and adventures. Neither of us have ever been to the city, so we’re super excited. We’re especially looking forward to discovering some new and delicious Chicago restaurants…but when I started to think specifics, I quickly got overwhelmed!

So, I figured I would ask the experts: what spots do you recommend?

We’ve got reservations at Girl and the Goatย (eek! should we try the goat empanadas?), and I’ve been eying the Publican…but I’d love some advice from those of you “in the know.” Where should we go? And what should we order once we get there? We’re adventurous eaters, and we love great cocktails as well. We’re willing to go out of our way for a great meal.

And speaking of finding great meals, have you checked out the Boarding Area blog Fly and Dine lately? Jason is an amazing resource (in fact, I’m hoping he has some Chicago restaurant tips for me)! His blog is a blend of the innovative (in-flight cocktail hacks, for example), and the practical (the LAX In N’ Out Burger trick),ย with a sprinkle of celebrity dish (pun intended) on the side.

Psst: today is an especially good day to check out Fly and Dine, because he’s running a $50 giveaway to The Counter…and he’s featuring an interview of me. ๐Ÿ˜‰

Here’s a photo of some Counter choices…and now I’m hungry. Thanks, Jason!

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  1. The publican is OK. It’s not worth the trek to west town. Their food can get a little too heavy and overseasoned for my taste. Go to Purple Pig instead.I’d try to get tickets to NEXT or Elizabeth. I like NAHA too. Go to Xoco for snacks (churro + caldo). If you don’t mind chains, Roka Akor serves good robata-grilled food. Avoid ramen in chitown.

  2. Even though it is traditional you can’t go to Chicago without trying Gibson’s Steakhouse. Also, nice little gem is Le Colonnial. Enjoy!

  3. Hi, Kendra,

    I enjoy your blog. As a former Chicago resident, I highly recommend Blackbird in the west loop (Avec next door is pretty good, too). If you want to try a Chicago sytle hot dog, go to Hot Doug’s (and don’t forget the duck fat fries) or Portillo’s (good fries, too). Have fun!


    • Hot Doug’s is great! But I don’t see a difference between the regular and the duck fat fries ๐Ÿ™ it’s only on Fridays by the way. If you like tacos Big Star is my favorite (cash only though ๐Ÿ™ no points!!!)

  4. Dinotto for Italian (on North Ave) and if the weather is nice sit on their outdoor patio.
    Portillos for fast food and a famous Italian Beef (Clark and Ontario)
    Maude’s for great French food (across the street from Girl and the Goat on Randolph Street).
    Japonais for sushi or just cocktails on their terrace (600 W. Chicago)
    The Godfrey Hotel: just opened and their rooftop terrace (for drinks, though just on the 4th floor is amazing, it is indoor/outdoor with a retractable roof-corner of Huron and LaSalle).
    Cafe BaBaReeba for tapas (Halsted Street)
    Gibsons, Lux Bar or Tavern on Rush (intersection of Rush/Bellvue). Great for steaks, salads, drinks. Great people watching area and next to some great shopping.
    Big Star for tacos and beers (cash only, Damen Ave). Located in another great little neighborhood.
    Hope this helps. Look up Time Out Chicago or the Eater website for further research. Have fun, this is an amazing city.

  5. Purple Pig and Naha are two of my favorites!

  6. Chicago Cut Steakhouse on the river is in my opinion the best steak in Chicago. Their outdoor patio is great too if the weather cooperates. I also agree NEXT is good if you can get tickets. I would also head to the Trump Tower’s outdoor patio. On a warm day it’s a great spot to take in the view and have a drink.

  7. I like Gilt Bar, on W. Kinzie. Great food, awesome drinks, nice atmosphere. Walking distance from most of the hotels. Mercat a la Planxa, on S. Michigan, is fantastic. Try the tasting menu with the sangria sampler. So yummy! And for breakfast, you have to go to Wildberry Pancakes, on E. Randolph. Super yum.

  8. BIG STAR!

  9. Purple Pig is great…I second that for sure. Hot Doug is great, but you will likely wait in line for an hour and its not around anything else…so probably not a good use of time. Portillo’s is fun and good for a quick meal! Of course you need to try Lou Malnatis or Giordanos (you can all fight over which is better) for deep dish…

  10. ptahcha says

    What’s your budget? Here are some:

    +1 for Blackbird and Purple Pig
    Moto (A good alternative to Alinea)
    Tru (budget buster)
    Squeeze in a deep dish pizza
    Try Rick Bayless’s place in ORD, or any of his restaurants
    Have a drink at the Trump Hotel
    Bin 36 has a fantastic by-the-glass wine list and small bites and it’s affordable

  11. The Aviary has some truly exceptional cocktails.

    If you can manage a reservation, Alinea or Next

  12. Jennie McCahey says

    Sable at the Kimpton Paloma on N. State is good. Small plates to share. Bacon Jam with melted brie and baguette is yummy and Dark Chocolate Souffle Cake peanut butter sauce, salted caramel ice cream (need I say more?). Bar had great cocktails.


  13. Kendra! I’ve got you covered! It depends a lot on what exactly you’re looking for and your location makes it harder to get to the cool, new spots (you’re in the middle of Touristville, USA, but there are still plenty of great options and even more if you’re willing to take a cab:

    1. Pizza. You’re closer to Giordano’s, but my favorite Chicago-style pizza (deep dish, not stuffed — that’s a whole other discussion, though) is Lou Malnati’s. Several locations. Go. Get the butter crust on whatever you order.

    2. Italian Beef. If you’ve never had an Italian beef sandwich, you’re in for a treat. Kind of like a French Dip, but with hot peppers (we call it giardiniera in Chicago) and a much better roll. My favorite is at Portillo’s (the only chain Chicagoans can get behind) but you’re fine at Mr. Beef on Orleans, too. Read about it here: http://www.foodrepublic.com/2011/11/29/portillos-combo-sandwich

    3. Cajun. In Chicago? I know. It’s weird, but Heaven on Seven (from Jimmy Banos — same guy behind Purple Pig) is truly delicious. It’s been there forever and it’s close to your hotel. Angry Chicken? Yes. Yes. Yes.

    4. Italian subs. This one is a car ride away. At Grand and May, there’s a little Italian grocery store called Bari Foods. Go to the back and order the best Italian sub of your life. They make their own giardiniera in-house. Also, stop next door at D’Amato’s bakery for amazing foccacia and cannoli afterwards.

    5. Steak. It’s not a Chicago classic like Gibson’s, but I’m partial to the new Mastro’s. I also love Lawry’s for prime rib.

    6. High-end cuisine. Sepia. Andrew Zimmerman is doing wonderful things here. In the same category at Blackbird and Avec.

    I second the Xoco nomination (NOMination), but you can get a similar sandwich when you’re flying through O’Hare. Just stop at Tortas Frontera, also from Rick Bayless. They have a few locations inside ORD and the tortas aren’t quite as good as Xoco, but they’re close and a lot of the menu items are similar/identical. Check it out: http://flyanddine.boardingarea.com/airport-chow-ritual-tortas-frontera-in-ohares-terminal-3/

    Have fun! Email me if you need any other recs at FlyandDine at gmail dot com.

  14. Brian M says

    Topolobampo/ Frontera Grill – great food, great tequila.

  15. Donna C says

    think neighborhoods when you think Chicago, so be sure to get out of the loop and try some very local fare. Ethnic food of every kind is available, including my personal favorite, Turkish! Hot Doug’s is awesome and Anthony Bourdain named it one of the 13 places you have to eat before you die!

  16. Alexis L says

    There are so many to choose from! Some of my current favorites: The Bristol, Vera, Naha, Macku, Takashi, Avec, Taxim, Embeya and Nightwood. Out of those, The Bristol, Avec and Nightwood do a great brunch.

  17. Get out of downtown at least once. Some of the best food in Chicago is away from the tourist center.

    Spend a night in Wicker Park. Eat at Mott St. Walk up Violet Hour or the Revel Room for great cocktails. Stop in to Big Star for a late night taco. There are loads of galleries, boutiques, etc to check out pre-dinner as well.

    Another favorite is Urban Belly. I have to disagree on the commenter’s opinion on ramen in Chitown. Bill Kim’s versions at Urban Belly are far from authentic – in a good way – and are really unique. The Asian Egg Noodle is my favorite, but you really can’t go wrong.

    Do you like beer? Map Room or Small Bar are great beer bars. Or check out DryHop or Revolution for excellent brew pubs.

    Perhaps my favorite restaurant in the city right now is Fat Rice in Logan Square. Their dim sum brunch is so delicious and creative, but get there about 10 minutes before they open to get a table!

    There’s obviously a lot more the city offers, but since I’m a WP resident, gotta put the ‘hood first!

  18. Other than the many good mentions above:
    Grace–Curtis Duffy’s cooking is fabulous
    Yusho–more casual, but Merges is excellent
    Schwa–you do run the risk that they decide to close if you can manage to get through and get a table

  19. smitty06 says

    Girl and the Goat and the Publican are the 2 places I bring people to the most when they are visiting. The Publican has an extensive beer menu, not so much for cocktails. For cocktails, I would recommend the Aviary, then walk down a few storefronts to ING to eat. If you dont want to go to 2 places, then head to MOTO for molecular gastronomy at its best. A splurge meal would be Alinea. It is my favorite restaurant in the world and its in my city! Lots of good places to get a steak. My favorite happens to be blackbird which is not a steak restaurant at all. Hot Dougs is awesome. Go early or late to avoid the lines. You may have to go on the weekend if you want the duck fat fries. I agree with the above poster that Le Colonial is very good but not trendy now. Also, Arun’s is amazing upscale Thai food. Its a tasting menu, but they let you request old favorites if you have been there before. I would skip Japonais. I think it is okay, but not special enough to choose it over something else. I guess by now you know there are too many places to try in Chicago. Best to plan a few more trips back.

  20. Points Pixie says

    Everyone – Wow!! Thanks for the array of suggestions. Clearly we are going to be eating our way through the city…and I agree with smitty06 that we will have to plan a few more trips back.

    Keep the suggestions coming if you’ve got any to add!

    Thanks so much. Can’t wait to try some of these. ๐Ÿ™‚

  21. Don’t waste your money at Girl and the Goat. Yeah, reservations are hard to come by there. Sometimes, it takes two months before you have a spot there seven’o clock on the weekend. But Food there is not good. The average at the most. Don’t give in to the celebrity effect. I have been there twice, both times food is average. I like Paris Club but all the aforementioned places are better than Girl and the Goat.

  22. Longman and Eagle, and the Sable kitchen & bar were two of my favs. Girl and the Goat (which you have reservations for!) and the Aviary were on my list ๐Ÿ™‚
    Enjoy Chicago!


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