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First Trip to Chicago-Can't Wait, Looking for Recommendations of Not to Miss

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I will be traveling to Chicago at the end of this week for a conference and extending our stay to visit with family. We'll be in the Windy City for a week and a half. Staying at the Westin on Michigan Ave. Here's my question, what places would you recommend for a food and culture lover? We won't have a car, but love taking public transportation and taking the L is on our list. (or whatever you call Chicago's subway). We'll be taking in a play, go to listen to some music and check out some of the city's wonderful architecture.
We want a mix of moderate to moderately expensive ($40-$60) per person including a bottle of wine to share to down right cheap dives ($20 or less). What are the absoluely not to miss places? We'll be keeping touristy spots to a bare minimum, although food tourism is another thing all together. Know about Gino's pizza, Hot Doug's. What about Moto's? And should we really spend all that money to eat at Charlie Trotter's? Looking forward to your recommendations. Thanks for your help!

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Hot Doug's
3324 N California Ave, Chicago, IL 60618

Charlie Trotter's
816 W. Armitage Ave., Chicago, IL 60614

Moto Restaurant
945 W Fulton, Chicago, IL 60607

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  1. Charlie Trotter's is roughly 3-4x per person what you have listed, more depending on your wine choices.

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    Charlie Trotter's
    816 W. Armitage Ave., Chicago, IL 60614

    1. Are you going to be here for 10 days of fun or 10 days of conference/fun? Because if you are going to be here for a whole 10 days of fun, man.. you are one lucky duck! You could spend 2-3 days exploring the downtown area and eating in the not to be missed various tourist areas (the only super touristy area with horrendous food options is Navy Pier. Go for the view). You can spend days in the neighborhoods and get a real true glimpse of Chicago. Let us now if you want advice on neighborhood restaurant tours. I know I'd would love to steer someone off the regular requested restauants on here - IF you are have the time to really explore. Also, I'd love to give advice on where to eat in the downtown area too. Any foods you can't get where you live?

      1. I'd try the Billy Goat. The burgers are OK but the ambience is what it's all about.

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        Billy Goat Tavern
        430 N Michigan Ave Lowr 1, Chicago, IL 60611

        1. You cannot afford Moto or Trotter's on your budget - not even close - even without wine.

          "Moderately expensive" in Chicago with a bottle of wine is probably closer to $100 a persion if "expensive" consists of Everest, Alinea, Trotters, Tru, L2o, and the like which will cost you closer to $200 a person with wine.

          You'd do well to look at some menus now and see what appeals to you. If you're really committed to ~50 a person with wine I'd suggest Cafe Spiaggia, Blackbird or Topolobampo at lunch, David Burke's Prime House, and The Gage.

          http://uhockey.blogspot.com

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          Alinea
          1723 N Halsted St, Chicago, IL 60614

          Moto Restaurant
          945 W Fulton, Chicago, IL 60607

          Cafe Spiaggia
          980 North Michigan Ave, Chicago, IL 60611

          Topolobampo
          445 N Clark St., Chicago, IL 60610

          Prime House Restaurant
          1401 Algonquin Rd, Rolling Meadows, IL 60008

          1 Reply
          1. re: uhockey

            David Burke's is only for lunch if you want to keep to your budget. Some of the other top tier places are easily more than $200/person, but you don't have to worry. Lots of good places in lower price categories.

            Personally, I don;t care for Gino's pizza, but you'll find opinions all over the place. I would steer you to Uno's, Due's, Lou Malnoti's or Pizanno's.

            But there are some really good options to consider that you can do for $40-60/person: Browntrout, Perennial, Le Sardine, Cafe des Architects (not the top of my list, but has a very good value in it's Chef's dinners), Sweets and Savories and more. You don't say where you'll be staying, but these are all accessible by public trans.

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            Browntrout
            4111 N Lincoln Ave, Chicago, IL 60618

          2. As a food lover, you should definitely take a Chicago Food Planet tour.

            http://www.chicagofoodplanet.com/

            They have 3 different tours: Near North (the original), Bucktown/Wicker Park, and a new Chinatown tour. I took the Bucktown/Wicker Park tour two weeks ago and loved it. I would have taken another if I had time. It's a great way to try places off the beaten path, learn about culture/history/architecture as you walk around, try food from 6-7 different places, and get restaurant recommendations for the neighborhood you're in. It's enough food to replace lunch. At the first stop, we had an entire Chicago-style hot dog, and by the 3rd stop, I was already full, so this definitely counts as lunch + a walking tour. Two stand-out places from the tour I took:

            Hot Chocolate - This is a restaurant with great food, but they specialize in dessert and hot chocolate (and homemade marshmallows). Get the medium hot chocolate (you get a cup of it on the tour)...it's like a melted bar of chocolate. I still daydream about it. And I've never had a marshmallow so soft and fresh.

            iCream - This place uses liquid nitrogen to make your ice cream on the spot. You choose what kind of milk, sweetener, flavors, and mixings, and they make it right there for you. I would go every day if I could.

            As for pizza...The Near North tour stops at a deep dish place and everyone gets a slice. The guide told me that Gino's was more for tourists nowadays, but I ignored him and went anyway. Honestly, it was just okay. Good, worth going I guess, but something tells me there are other places in Chicago w/ better deep dish. I felt the same way about Unos.

            Anyway, if you want to learn about food & culture, one of these food tours is worth your time. You get both, and you'll also probably find some spots you want to return to on your stay. Have fun!

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            Hot Chocolate
            1747 N Damen Ave, Chicago, IL 60647