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First time in Chicago

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Hi there,
My boyfriend and I will be visiting chicago for the first time in there end of June. We're looking for some guidance in getting a great taste of the city including favorite pizza joints, hot dog place, looking for good polish food and anything else that stands out. Were in our late twenties and from the NYC metro area so are pretty adventurous eaters. We'd like at least one nice night to celebrate our anniversary. We're staying in heathen downtown area on south michigan ave .
Thanks in advance for your help!

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  1. If I had a first trip to spend in Chicago, here's what I would pick, starting with the most "must have" experience and working down from there:

    1. Alinea. Yes, it's expensive ($225+ per person plus beverages/alcohol and tax/tip), and it's dressy. It's also one of the best restaurants in the world and the food experience of a lifetime. (My recent dinner there was one of the two or three best in my entire life.) They sell advance tickets on their website and lately they're not too terribly hard to snag. Dinner only, closed Mondays/Tuesdays. www.alinearestaurant.com See below for more "special occasion" restaurants for your anniversary dinner.

    2. Deep-dish pizza, a Chicago specialty. Lou Malnati's, regarded by many as the best in town, has a location at 8th and State near South Michigan Avenue. You can phone ahead with your pizza order to avoid waiting 30-45 minutes while seated for your pizza to bake. www.loumalnatis.com

    3. Contemporary Mexican. This is something you don't get back home and isn't found many other places in the States, either. I'd start with Rick Bayless's Frontera Grill or Topolobampo. www.rickbayless.com/restaurants Another option is Mexique, in West Town. www.mexiquechicago.com

    4. Garrett's Popcorn. There are several locations in the Loop, or pick some up at O'Hare before your flight departure. Caramel popcorn (with or without cashews or pecans), cheese popcorn, or the "Chicago mix" of the two. www.garrettpopcorn.com

    5. Breakfast/brunch. Chicago has a huge selection of breakfast-focused restaurants. Bongo Room's location at Roosevelt (12th) and Wabash, near South Michigan Avenue, has creative pancakes (e.g. pretzel pancakes with white chocolate caramel sauce). www.thebongoroom.com Jam, near the Logan Square stop on the CTA Blue Line, has the creativity you'd find at the high-end temples of haute cuisine. www.jamrestaurant.com

    6. North Pond. This is a special place unique to Chicago. They have excellent contemporary American cuisine from James Beard Award winner Chef Bruce Sherman. What makes it unique is its exquisite setting in the middle of the park, facing its namesake pond, with the city skyline looming over the opposite shore. Also a good spot for Sunday brunch. www.northpondrestaurant.com

    7. The French Market, located just west of the Loop in one of the train stations, is worth a visit. It has several dozen food booths and these include some of the very best that Chicago has to offer. Highlights include the croissants, entremets, and French macaroons at Vanille Patisserie; the cheeses and sandwiches at Pastoral; Montreal smoked meat at Fumare; barbecue at Lillie's Q; and banh mi at Saigon Sisters. www.frenchmarketchicago.com

    8. Small plates. Some of our very best restaurants right now specialize in small plates of one sort or another, and are moderately priced. Sable specializes in contemporary American cuisine and craft cocktails; don't miss the sweet corn creme brulee. www.sablechicago.com GT Fish & Oyster specializes in seafood and craft cocktails. www.gtoyster.com Mercat a la Planxa has tapas and is on South Michigan Avenue. www.mercatchicago.com All of these accept reservations, for lunch or dinner. The Purple Pig has Mediterranean-ish cuisine, but does not accept reservations, and waits for a table are horrendous (120+ minutes at dinner well into the evening, not quite as bad at lunch); if you want to go without a long wait, go mid-afternoon or late at night. www.thepurplepigchicago.com

    Here are more recommendations for your anniversary dinner, in addition to the previously-mentioned Alinea. Along with Alinea, Grace is one of the very best restaurants in Chicago. Like Alinea, you're probably looking at spending $600-800 for two, including moderate alcohol and tax/tip. www.grace-restaurant.com But you don't have to spend this much for a special occasion type place. Everest is a short walk from South Michigan Avenue and has terrific contemporary French cuisine; expect to spend $250-400 there. www.everestrestaurant.com And even less, in the $175-250 range, are the previously-mentioned North Pond as well as Naha. www.naha-chicago.com Furthermore, North Pond and Everest are two of the most romantic restaurants in Chicago, North Pond for its setting in the park, and Everest for its view from the 40th floor of the Midwest Stock Exchange Building.

    1 Reply
    1. re: nsxtasy

      Wow! Thank you so much for such an informative and extensive list! I'm so excited to visit, and hadn't heard of the market yet. Thanks again :)

    2. Nsxtasy's list is excellent. Of course there are tons of other options but you can't go wrong with most of those. I would add:
      Hot dogs: Hot Doug's is the most famous, but I'm a fan of Frank 'n Dawgs on Clybourn.
      Also, it will be farmer's market season when you're here. Foodies should definitely check one or two out. I frequent Green City Market in Lincoln Park, but lots of people like the Logan Square one, too. It's on Sundays so you can combine it with brunch at Jam or Lula Cafe.

      11 Replies
      1. re: msmolly

        Your time is likely to be precious, and if Hot Doug's is on your list, you should get there before it opens so that you don't have to experience the legendary long line.

        1. re: BoneAppetite

          Thanks for the tips! I very well may go to both hot dog joints.

          1. re: Jsimao105

            Personally, I'm not a big fan of Hot Doug's. Not just because of the inconvenient location (which it is) or the ridiculously long lines (which they are - I waited 90 minutes), but because the hot dogs are nothing all that great, IMHO. And neither were the duck fat fries; I thought their regular fries were better, but neither were the best fries around. I'd rather go to Edzo's, any time - best burgers, best fries, and best shakes on the planet! www.edzos.com

            Even so, you can get hot dogs and burgers anywhere; they're hardly unique to Chicago, which is why I wouldn't choose either one on a first trip to Chicago. It's like going to a steakhouse on a first trip here. It's not that we don't have good steakhouses; we do. But so does every other big city in North America, so you'd be eating something you can easily get back home.

            1. re: nsxtasy

              No one should ever go to Hot Dougs for the hot dogs!

              It is a place to eat really interesting "encased meats" like "Juniper and Garlic Pork Sausage with Gin & Tonic Mustard and Smoked Gouda Cheese" or "Sweet Chinese Pork Sausage with Hoisin Mayonnaise and Asian Slaw à la Tracy."

              I agree that the location is out of the way, but if someone wants to get a feel for Chicago and its people, those lines engender some really great conversation.

              Edzo's does a good burger. But a burger not only ain't a hot dog, it ain't a Hot Doug's sausage.

              My preferred alternate would be Franks and Dawgs on Clybourn, which has only gotten better over the years.

              1. re: chicgail

                FWIW, I tried the other "exotic" sausages while I was at Hot Doug's. None of them impressed me much. I realize it has its fans, but I'm not one of them.

                As for a "feel for Chicago and its people", all the people around me while waiting in line at Hot Doug's were from outside the city. I can only conclude that it's a big hangout for tourists! :) You'll probably find a lot more locals at Franks 'n' Dawgs. Or at Portillo's, for that matter. Of course, unlike Hot Doug's, you won't be spending a couple hours in line at either place - which most of us would consider a good thing.

                OTOH, if you feel that you absolutely MUST go to Hot Doug's to see what all the hoopla is about, by all means go! Then you can decide for yourself whether or not it's worth the trouble.

                1. re: nsxtasy

                  Skip the Chicago dog at Hot Doug's, because the fun is the "entrée on a bun" route. By the way, foie gras is back.

            2. re: Jsimao105

              No one has answered your request for Polish recommendations. If you don't have a car, you can take the Blue Line train to Podhalanka. If you do have a car, Smak-Tak is in a class by itself.
              Also, I am a big fan of Hot Doug's. But Franks 'n' Dawgs is not a bad alternative if you don't want to wait in line.
              In terms of your nice night out, Acadia is convenient to your location. If you have the bucks, Grace would be even better.

              1. re: Polski

                >> Franks 'n' Dawgs is not a bad alternative if you don't want to wait in line.

                I agree. Also, its location is a lot more transportation-friendly.

                >> Acadia is convenient to your location.

                That depends on what you're comparing it to. More precisely, as confirmed by Google Maps, Acadia is one mile from the Hilton Chicago, which is where most folks who mention South Michigan Avenue are staying. You *could* walk it, but... that part of the South Loop is not a bad neighborhood, but I've found that it can be pretty deserted, with very little activity on the street in the evening. That stretch of South Wabash is slowly developing, but much of it is still undeveloped, such as the vacant lot next door to Acadia. And you should also be aware that Acadia has no exterior signage whatsoever; the only indication that there's a restaurant there is the small sign for the valet parking.

                By way of contrast, the places I mentioned as being near South Michigan - Lou Malnati's, Bongo Room, Mercat a la Planxa, and Everest - are all within a few blocks walk from the Hilton Chicago, through busy built-up areas. (Distances: .2 mile, .4 mile, <.1 mile, and .6 mile, respectively.)

                1. re: nsxtasy

                  Last time I ate at Everest I was physically threatened by a very aggressive panhandler on exiting the building, so I would advise a cab after dinner anywhere in the South Loop.

                  1. re: Polski

                    Wow, that's REALLY unusual. The Loop - and Everest is in the Loop, not the South Loop - is ordinarily quite safe, even in the evening. Of course, normal precautions are wise anywhere in Chicago, just like in any other big city.

                    1. re: Polski

                      I agree with Nsxtasy. My office is in the South Loop. It is not unusual for me to walk back to my car parked in the South Loop in the evening after a social event conducted further north (say in the Loop proper or north of the River). I have done so alone as late as 10 or 11 pm and I've never felt uncomfortable, even though I am a small woman.

                      I do typically walk along Michigan Ave as it gets a lot of foot traffic.