We want to get blown away by the Windy City

Do we have any peeps from Chicago in the crowd? Are there lovers of deep dish pizza and hotdogs with pepperoncini in our midst? I hope so, because we need your help.

In November, Mike and I are heading to the Windy City for a whirlwind 4 day vacation as we celebrate our first anniversary as an Official and Legally Bound Married Couple. Before even looking at the attractions, my first thought was…where to eat? After only about 4 minutes’ exploration online, I am now saying…..where NOT to eat?

You guys, Chicago looks like a Foodie WONDERLAND. I am almost beside myself and I barely know where to start. Do we savor the creative molecular gastronomy at some of the world’s top restaurants or spend our scheckels at the elite Avenues at the Peninsula? Do we go to Joe’s Steak and Seafood for stone crab or Shaw’s Crab House for the oyster sampler? Is the “real” Chicago deep dish at Frankie’s on 5th, Uno‘s or Lou Manalti’s? Where IS the best place for steak, hot dogs and BBQ? Oh, the UNKNOWN!!

Right now, this is my work in progress:

This vague and amorphous hatchling of a plan is really all we have to go on right now, and so I appeal to you for help. If there is a must-try restaurant that we really need to visit, will you let us know? If there is a Mom and Pop hole-in-the-wall diner (which are always and without fail my favorite places to eat) can you recommend it? And for god’s sake, please help us sift through our options for the best Sunday brunch. Even if you happened to be in Chicago on an overnight business trip 3 years ago but you can’t help smiling at the memory of a tiny little pub with the best selection of microbrews….we would love to hear from you. Any and all advice (including the “stay away from XYZ..”) would be so very welcome and appreciated.

Look, I really need your help on this one, because if left to our own devices, Mike will choose to do nothing but sample Chicago’s hot dogs for 4 days straight as I tug his sleeve saying, “Oh, ignore the warning sign outside. That place looks like it has total potential! Let’s go see….”

  • Amy

    We loved the Gage – a great gastropub type place right across from the Chicago Art Institute. Fabulous local beers on tap, great food (and heavy on awesome cheese) and a lovely (though not overly intimidating) space.
    My husband and I looooved Topolobampo if its at all possible for you to get a reservation. Fronterra grill was also amazing, but my carnivorous husband stole half of my vegetarian tasting menu dishes at Topolobampo to my utter amazement. And if you can – sit at the bar in Fronterra and have some of their specialty margaritas – so amazing!

    • http://www.choosy-beggars.com Tina

      Amy, that’s awesome!! Thank you so much for the tips. I was torn between Fronterra and Topolobampo, but was leaning towards Fronterra for Saturday brunch. Now you make me rethink that. The Gage sounds charming and EXACTLY up our alley. Mind you, the mere mention of cheese and you must have known that I would be hooked 😉

      Thanks again for some great recommendations, they are very appreciated!

  • Erin

    Obviously everyone has their opinion about “the” deep dish pizza place. As a life-long Chicagoan my recommendation is and always will be Gino’s East pizza (preferably with the sausage patty, not crumbled). I generally consider deep dish pizza a must try Chicago food, but not essential to my daily life. But now that I have been on the East coast for 3 weeks I am craving it.

    As for the bar-none best hot dog and fries, if you are willing to venture a tiny bit into the suburbs you should definitely head to Gene and Jude’s in River Grove. It’s a tiny dive of place, three things on the menu (hot dogs, tamales, and fries) but it is so good. If you can, avoid it at the lunch rush, there will be a line, possibly out the door and down the block.

    Now I can’t wait to get home and have this food again!

  • http://everythingsun.blogspot.com Mike

    I live in the ‘burbs so I don’t know a lot of mom and pop type places in the city, but here are some of my favorites.

    I prefer Lou’s for pizza. I think it Is the best of the deep dish pizzas that I have had.

    I like Morton’s for steack, but they are elsewhere, so you may have been there before. Gibson’s is very good too.

    That’s all I have. Enjoy Chicago!

  • Beth

    I imagine you will visit the Sears Tower, however if you want the same view with cocktails and appetizers, try the Signature Lounge at the 96th floor in the John Hancock building. You can’t beat a night time visit. Avoid parking there, take the elevator to the top, and get out and have cocktails, appetizers and enjoy the nighttime view. We took my sister in law and we didn’t even go to the viewing floor and pay the $25 for the viewing tickets. Why bother, when you can see it all from the lounge. The prices for drinks are a little higher than normal, but not outrageous, two martinis would likely equal the viewing floor ticket. Even the ladies room had as great view! Also, Giordano’s by the Sears Tower has a great deep dish pizza.

  • Jthan

    Seconding the Gino’s deep dish sausage (patty style.) Be prepared to wait 45 minutes to an hour for one, but don’t eat appetizers while waiting. That pizza will FILL you UP! Also, bring a permanent marker or two with you, Gino’s encourages graffiti in certain areas of their buildings. You can goof off doing that and drinking beer while waiting for your delicious pizza.

  • Becca

    I don’t even like deep dish, as I am a heathen and will never be a true midwesterner (I am a 10-year transplant to Chicago). Some favorites:

    -Xoco (great tortas, right next door to Frontera)
    -Hot Doug’s (awesome if you like hot dogs and sausages)
    -Magnolia Cafe in Uptown (close to the Wilson red line; on Wilson near Magnolia) is fantastic for brunch – try the smoked trout hash!
    -The Publican – pork-heavy menu, fantastic beer list. It’s styled after a German beer hall. Get reservations.
    -Big Star is owned by the same folks who own The Publican, $3 tacos, cheap beer, and lots of whiskeys to try
    -I second the recommendation for The Gage, and will say that their corned beef hash is amazing.
    -Hopleaf in Andersonville (take the Clark bus to get there, or it’s a slightly longer walk from the Berwyn red line) has a Belgian-ish menu (mussels!) and an enormous beer list. Get there early or expect a wait. Or if you go late, you can catch the 11p (I think) showing of Too Much Light Makes the Baby Go Blind at the theater around the corner (Neo-Futurists; it’s 30 plays in 60 minutes and really fun.)
    -Webster’s Wine Bar is…a wine bar! With a tasty food menu, too
    -Bluebird is a more beer-y place owned by the folks who own Webster’s.

    I could go on, but these are the first things that jumped to mind! Have a great time – Chicago is an amazing city!

  • http://thespitefulchef.blogspot.com Kristie

    OMG. I am sooooo jealous. Chicago is not only my all-time favorite food destination, it’s also the home of my two favorite vacations ever. First, I don’t know what your ability is to save up between now and then for a crazy splurge, but Chicago is the home of Alinea, which has provided the two most educational, artistic, thought-provoking, and delicious meals I’ve ever had. It was like a four year college of awesome in one night. You’d have to get reservations ASAP, but it’s worth every penny. That said, it’s prohibitively expensive on any kind of reasonable budget (the times we went were before we had a kid, owned a home, etc).

    Topolobampo is fabulous, and I have a good friend who works there, so I could see if she could show you the kitchen or give you some kind of insider meal tip. Xoco and Frontera are both great, but aren’t in the same league as Topo. Do a tequila flight for me.

    Argo Tea is in Chicago, and is like a wet dream Starbucks of tea. Their bubble tea is both affordable, and the bubbles are made from nata de coco, so it’s a very different (and completely delicious) treat. I went there three times a day when I could. And the Carolina Honey Tea is good for what ails you, whatever that may be. I’m sick with jealousy.

    I can’t remember the name of the pizza place we loved, but it was near the corner of Halstadt and Armitage… it blew Lou Malnati’s out of the water.

    Hot Doug’s is a handmade sausage and hot dog place. Get there EARLY because lines develop quickly, and are LONG. Worth it though. Everything is handmade and fantastic, and they serve them with duck fat fries. Oh, and they only take cash–don’t forget! We forgot, and my brother had to run 5 miles to the nearest ATM (that he could find). Seriously, that meal still brings tears to my eyes. And it’s inexpensive and casual.

    There’s a “Greek quarter” of sorts with FABULOUS gyros and (inexplicably) delicious french fries.

    The aforementioned Xoco (which is right next to Topo) is a much less expensive takeout-style Mexican restaurant (also a Rick Bayless creation) and they have pibil sandwiches, which are made from the same recipe that won him Top Chef All-Star fame. Plus, they make in-house, hot churros. And a daily dessert that always blows my mind when he tweets it.

    Homaro Cantu has a restaurant there called ING, where they do tastings that experiment with those miracle berries (that turn sour things sweet). It looks pretty cool, even just for the flavor-changing cocktails. Like Willy Wonka shit.

    Seriously. My jealousy is forcing liquid weakness out of the corners of my eyes.

  • http://thespitefulchef.blogspot.com Kristie

    I just got so excited that I lost all track of what you had already written. Do Alinea if you can get a reservation. Moto is owned by Homaro, and the ING restaurant is much less expensive with the same playfulness as Moto has shown.

  • http://thespitefulchef.blogspot.com Kristie

    And the best brunch was at Toast.

  • Kelsey

    I lived in Chicago for three memorable years, and it’s one of my favorite places, both to live and to eat.

    Deep dish: I really love Giordanos, to the point where I had a pizza flown to me on dry ice for my 30th birthday. I would, however, recommend getting a plain cheese pie; other stuff is nice, but a Chicago deep dish pizza is a serious phenomenon and my sense is that you will not want anything to distract from the main event, which is undeniably cheese. In any case, they have beautiful buttery crust.

    Brunch: you must try Orange. It is crowded and busy on weekends, but their brunch is to die for. They have PANCAKE FLIGHTS! Like, several mini stacks of silver dollar pancakes, all with a slightly different flavor profile. I love them. http://www.orangerestaurantchicago.com/Main.html

    My favorite place in Chicago is Hopleaf (http://hopleaf.com/), a bar with literally hundreds amazing beers that also serves great food and bar snacks, and if you go there, I will second the recommendation for the Neo-Futurists; it’s hard to explain how awesome it is.

    If you like Korean, there’s a great restaurant in Andersonville called Jin Ju which is just delicious.

    And finally, don’t ignore the South Side; people avoid it because it is the ‘dangerous’ (annoying code for ‘less white’) part of the city but I used to live there and loved it. Amazing soul food all over the place and some funny little things you won’t get anywhere else–there used to be an Indian-soul food fusion buffet near my house that was unlike anything I’d ever seen. Fewer places have web presences, but seriously, just head to Hyde Park and start exploring. Also, if you like jazz, there is always great stuff happening at the Velvet Lounge (http://www.velvetlounge.net/)

  • Kelsey

    Oh! I forgot to add that you should absolutely get yourself to Pilsen for Mexican food (it’s the big historically Mexican/Latino neighborhood) and to Devon Street on the North Side for a huge selection of amazing Indian food, particularly North Indian (protip: the street is pronounced deh-VOHN, not like the first name)

  • E.

    Another vote for Lou Malnati’s, the Signature Lounge, Hot Doug’s and Topolobampo. If you want to try some stuffed pizza a little out of the way check out Pequod’s over by DePaul.

    Everyone I know who’s taken out a loan to eat at Alinea has gone on to describe the experience in orgiastic detail and said it’s totally worth it. I don’t know anyone who’s eaten at MOTO, though, so I can’t do much comparison.

    • Sarah

      I wholeheartedly second the Pequod’s recommendation. It is to die for.

  • flyingbird

    Go to a Garret’s for popcorn ( http://www.garrettpopcorn.com ). I still dream about the amazing cheese popcorn found in Chicago. Amazing flavor, grease staining the bag, fingers orange for days. The chicago mix is caramel corn and cheese…addictive. It’s a meal.

  • Laura K

    The best pizza. Not just in Chicago. In America.

    http://www.gq.com/food-travel/alan-richman/200905/pizza-american-pie-25-best

    Great Lake Pizza. Three pizzas on any given night with two or three options for each. It’s a few blocks from Hopleaf and the Neos (as Becca mentioned above).

    But first! Learn the rules. Follow the rules. The Yelp reviews have the details (including lots of hilarious whining from people who did not follow the rules or who don’t deserve tastebuds), but they boil down to this: get there 15-30 mins before it opens, and pick a pizza with or without the listed options (SLICED GARLIC YES; HERBS YES omg fresh thyme) but don’t bother asking for anything else. If you do get there late, you’re not getting a table, but you can place an order. Do so, go down to Hopleaf (or the below-mentioned In Fine Spirits) for the hour to hour and a half it will take, then come back and eat it on the sidewalk if you have to. Eat it hot. Then die because you are all done with food. (Mindy Segal ice cream was available when I was there; get it if you have room.)

    http://www.yelp.com/biz/great-lake-chicago

    Bonus suggestion: Pop into In Fine Spirits around the corner and down a few stores on Clark Street and pick up a bottle of wine or Metropolitan beer. It’s close enough that one of you can do this after you’ve secured your table if need be.

    I moved away a year and a half ago and still dream about it.

  • http://www.twitter.com/artychoke jen

    I emphatically second (or third or fourth) Frontera Grill, Xoco, and Hot Dougs. Food and service were amazing at Frontera and prices were very reasonable. There were no reservations so we arrived around 5 and waited in line for a short while and got a table. Xoco was great for breakfast and lunch sandwiches. Hot Dougs is out of the way but the hot dogs were really good. Not sure if it was worth a 40-minute line though.

    The Map Room is a great bar with an amazing beer selection. The only bad thing we ate on the whole trip was Pizzeria Uno deep dish pizza. It was bland, greasy mush. I’m sure Chicago has much better pizza.

    Make sure you go on a boat on the river!

  • Mimi

    I cannot recommend Big Star enough! On my last trip to Chicago, I loved it so much that I went there twice for their fish tacos and pork belly tacos. Guac is also a must.

    Seems like Chicago is currently in love with nose-to-tail gastropubs. We tried Girl and the Goat, which was good but not executed perfectly. Our waiter at Girl and the Goat actually highly recommend Publican…

  • Laura K

    Oh! My mom’s favorite, and a totally regional thing that doesn’t get much attention: Italian beef sandwiches. Thin sliced beef, pepperoncinis, cheap Italian bread rolls dipped in … beef juice? I don’t know what that is. I’m a vegetarian so don’t register many details about it (if I can help it) but it’s definitely traditional and popular. Luke’s on Jackson is always busy at lunch with Loop workers.

    Oh oh! And Russian Tea Time is hilarious. Fantastic black current tea, dark brown bread, and infused vodkas. The food is okay, but I’ve only had their cold borscht (good!) and pierogies (perfectly adequate).

    Oh oh oh! Actual fancy place recommendation! Spiaggia (or Cafe Spiaggia, its sibling) is heavenly Italian. President Obama and the missus went back to Chicago for their first anniversary after the move to DC, and this is where they ate. Presidentially good.

  • Erin

    Oh, Italian beef sandwiches. I am craving one and they just don’t exist outside of the Chicagoland area. Thin sliced beef, giardinara, juicy, slightly spicy. Just awesome. I would recommend Al’s Beef. There are a few locations, but the original location is on Taylor Street. Depending on how much of a mess you want to make you can get it dipped or not. They also have good hot dogs and sausage. If you can’t choose, you can do what my dad does and order a combo, Italian beef and sausage.

  • Tia

    Lou’s for pizza

    Hot Doug’s for the ULTIMATE Chicago hot dog. It’s cash only, but on Saturdays, there are duck fat fries, and the experience of waiting in line.

    Get some Italian Ice on taylor st. Nom.

    You can get a super fab brunch at Lula’s Cafe, and omigah amazing dinner at Home Bistro.

    I feel that I don’t need to go to bat for these places, because if you hit up the yelp pages, you will see. <3

  • http://www.choosy-beggars.com Tina

    OH MY GOD. You guys, you have totally blown me away here. I cannot tell you how much I appreciate all the absolutely wonderful recommendations, except to say….THANK YOU, THANK YOU, THANK YOU. From pizza to Italian Beef, dogs to pugs and everything in between, this trip is going to be epic.

    We really appreciate the time you took to comment, and can’t wait to try and suss out your suggestions!! Thank you again 🙂
    Tina & Mike

  • http://thespitefulchef.blogspot.com Kristie

    Chris will be writing a thank you letter to you soon, since his wife was so jealous that she ended up purchasing tickets for a long weekend in Chicago, without 100% consulting him… And I’m eating nothing but freezer food for a month so we can do Alinea. Maybe we’ll see you there 😉 In a not-stalker way.

  • Lisa

    There was just a place on Food Network that makes meatloaf cupcakes with mashed potato frosting. Haven’t been there, though.

    Places I’ve been:

    I know you guys love meat, but The Chicago Diner is awesome. I’m an omnivore, but the food was really good.

  • BBridget

    Rose Angelis is my favorite restaurant of all time. It’s Italian but oh so much more. Just check out their menu- I have dreams about the duck tortellini and it is very reasonable. They don’t take reservations but they will call the bar across the street (Maeve) and let them know when your drink is ready. BBQ Smoque is incredible, cheap, and a recent Food Network favorite for a good reason. I agree the Gage is a must but Carnivale is terrible. Also, the best brunch in Chicago is at the Bongo Room in Wicker Park! I could do this for hours but I’ll give you just one more- Twin Anchor Steam was Frank Sinatra’s favorite restaurant in Chicago, they have great ribs and an awesome divebar feel. Have a Gumballhead Beer while you are there from 3 Floyds, you won’t forget it!

  • mirinblue

    Giordanos for pizza
    Alinea-you just HAVE to
    Purple Pig-get the stuffed olives
    The Girl and the Goat
    Topolabampo

  • Julie

    Grant Achatz’ next restaurant, Next. This season is CHILDHOOD. Tickets are sold out but if you connect with them on FB you will be notified of same night tables being released (I recommend subscribing to receive mobile phone notifications because you have to be FAST with your email response to snatch up a table). Much less expensive than Alinea, same creative genius, and possible to experience during your trip. If you haven’t been following the Next concept, it can be pretty daunting to figure out, email me and I’ll be happy to provide a tutorial. Also, great burgers at DMK, up near Wrigley Field.