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Jun 2, 2013 06:45 PM

First time visitor to Chicago in search of 4 days of great eating.

I'm tagging along with my husband while he attends a conference in July.
I will have 4 full days (Wed-Sat) on my own to discover the splendor and food of Chicago!
We are staying at the Hyatt Regency O'Hare but I plan to do a lot of walking and using the L for transportation.
I would love to try out local favorites while wandering different neighborhoods. Anything along the Blue line between O'Hare and the Loop would be preferable but anywhere for a single woman, and within safe walking distance to any L stop would be great.
I will have the hubby with me during the evenings and neither one of us have been to Chicago before, so we would love to try things quintessential "Chicago". Deep Dish and Hot Dogs to be sure but would love to visit some local "dives" and neighborhood favorites too.
As far as $ goes I love "cheap eats" and great food trucks and for a sit down dinner I usually like to keep it around $20pp per meal for food. We aren't big drinkers so no need to worry about that expense. We will spend more if it is worth it and will be celebrating a birthday so recs across the board are very, very welcome.
I've started my research and will update with my ideas and findings but any help will be greatly appreciated!

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  1. So you're open to anywhere geographically, and you prefer inexpensive but you're willing to spend more if it's worth it. That certainly casts a wide net, LOL!

    Along the Blue Line, the best options include Jam for breakfast/brunch near the Logan Square station, Lula for farm-to-table cuisine near the same station, Piccolo Sogno for Italian near the Grand station (request the lovely outdoor patio if the weather's nice), Bongo Room's Wicker Park location for breakfast near the Damen station, and Smoque for barbecue near the Irving Park station.

    For options downtown and elsewhere, someone else posted that they will be in Chicago for 36 hours on a first visit to Chicago. Here's what I posted there ( ), with some edits added:

    First, just to get an overview of what Chicago has to offer, this discussion tells what foods and places are unique or specialties in Chicago, foods that Chicago is particularly good at:

    first time Chicago -

    If I had 36 hours 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 ($210+ 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. They sell advance tickets on their website and lately they're not too terribly hard to snag. Dinner only, closed Mondays/Tuesdays.

    2. Deep-dish pizza, a Chicago specialty. Lou Malnati's, regarded by many as the best in town, has a location at State and Rush near the north end of the Mag Mile and on Wells west of the south end of the Mag Mile. Pizano's has a location on State north of Chicago Ave. (EDIT: Pizano's also has a location in the Loop.) The original Uno and Due are near the south end of the Mag Mile. This works for lunch or dinner. At Malnati's and Pizano's, you can phone ahead with your pizza order to avoid waiting 30-45 minutes while seated for your pizza to bake.

    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, both a short walk from the Mag Mile. Since your visit is soon, it's probably too late to get a reservation at Frontera Grill or a dinner reservation at Topolobampo. That leaves the following options. You may still be able to get a lunch reservation at Topolobampo. If you arrive at Frontera Grill 15-20 minutes before they open the doors, you won't have to wait. You can otherwise wait 90+ minutes to be seated at Frontera Grill. Or you can go to one of our other contemporary Mexican options: Mexique, in West Town (take #66 CTA bus two miles west on Chicago Ave); Salpicon, in Old Town (walkable from the north end of the Mag Mile); Mundial Cocina Mestiza (EDIT - they are closed); or Mixteco Grill (near the Montrose station on the CTA Brown Line). All of these are open for lunch or dinner.

    4. Garrett's Popcorn. This is a snack you can fit into your schedule; there's a location on the Mag Mile, or pick some up at O'Hare before your flight departure. (Currently open in Terminals 1 and 3, but their store in Terminal 5, the international terminal, won't be open till later this year.) (EDIT: There are also several locations in the Loop.) Caramel popcorn (with or without cashews or pecans), cheese popcorn, or the "Chicago mix" of the two.

    5. Breakfast/brunch. Chicago has a huge selection of breakfast-focused restaurants. 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. M. Henrietta, at the Granville station on the CTA Red Line, has lots of great stuff. Bongo Room, at the 12th/Roosevelt/Wabash station on the CTA Red, Orange, and Green Lines has creative pancakes (e.g. pretzel pancakes with white chocolate caramel sauce). (EDIT: Their Wicker Park location is near the Damen station on the Blue Line.) Southport Grocery, near the Southport station on the CTA Brown Line, has bread pudding pancakes and adult pop-tarts.

    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. During the week, open only for dinner. (EDIT: Also open for Sunday brunch.)

    7. Small plates. Some of our very best restaurants right now specialize in small plates of one sort or another, and are moderately priced. Several are a short walk from the Mag Mile. Sable specializes in contemporary American cuisine and craft cocktails; don't miss the sweet corn creme brulee. GT Fish & Oyster specializes in seafood and craft cocktails. Mercat a la Planxa has tapas. All three 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. After all, with only 36 hours here, you really don't want to spend a lot of time waiting for a table (avoid Avec too for that reason).

    1. Hot Doug's is probably the most famous hog dog place in Chicago and has the corresponding longest lines. There's a whole thread here though on the best dogs in Chicago.

      As for other cheap eats: I think Xoco would be a good representation of the Rick Bayless influence on the city and Mexican cuisine in America. Also, Au Cheval for the signature hamburger and a taste of Brendan Sodikoff's cocktail mini-empire. Harold's fried chicken shacks (dozen of locations in less visited parts of the city) has an emotional connection for any good resident of the South Side.

      3 Replies
      1. re: W42

        Hot Doug's isn't a hot dog place at all. It's a place that specializes in encased meats - sausages, etc.

        And if you want a good representation of the Rick Bayless influence, you would be better off trying one of his two restaurants featuring creative contemporary Mexican cuisine - Frontera Grill or Topolobampo - rather than XOCO, which features conventional Mexican "street foods" similar to what you can find in any city in the country.

        1. re: nsxtasy

          Just to clear: it's true that Hot Doug's has a lot of other options on the menu (that's where the higher profit margins are). But a lot of us on that other thread agreed that they do one of the best renditions of the "quintessential" Chicago style hot dog. Since that's what kiki2U said they wanted, I'm not sure what the point you're trying to make is. Locals may feel the need to correct visitors on what a "chicago style hot dog" is or what defines a "hot dog place," but the out-of-town friends I've sent to Hot Doug's weren't uptight about purity tests since they heard the dogs were pretty authentic.

          Also, I agree that Frontera Grill and Topolobampo are more special and better ways to experience Rick Bayless's influence. But I don't see how either are really the best options when the OP "loves cheap eats," food trucks, and under $20/person for dinner. For that matter, kiki2U should know that a lot of the places listed on your cut/pasted advice are above that price range and should be saved for the birthday dinner.

          1. re: W42

            >> I'm not sure what the point you're trying to make is.

            The point is, Hot Doug's involves a lot of inconvenience - a long trip from most parts of the city, plus a long wait on line. If you're doing it because you want a classic Chicago-style hot dog, you can get that from lots of closer places (like Portillo's) without all the hassle. (And if you want encased meats, Franks 'n Dawgs has a nice selection in a more convenient location without the long waits.)

            >> I agree that Frontera Grill and Topolobampo are more special and better ways to experience Rick Bayless's influence. But I don't see how either are really the best options when the OP "loves cheap eats," food trucks, and under $20/person for dinner.

            Most dinner entrees at Frontera Grill are $23.50 or less, which meets the stated criterion, "around $20pp per meal for food". Furthermore, one can experience both Frontera Grill and Topolobampo for under $20/person for lunch. Lunch is often a way to meet a restrictive budget, as long as the lunch offerings offer the same level of creativity as at dinner, and that description applies to Frontera Grill and Topolobampo.

            Another way to experience Rick Bayless's influence is to try contemporary Mexican cuisine from other chefs, at places such as those I mentioned above. For example, you can find entrees for $20 or less at Mixteco Grill and Salpicon. You can get an idea of Bayless's influence on others by reading testimonials such as the one by Raul Arreola, the founding chef at Mixteco Grill, at

            >> For that matter, kiki2U should know that a lot of the places listed on your cut/pasted advice are above that price range and should be saved for the birthday dinner.

            I did indeed copy the advice from a previous post because so much of it applies to kiki2U's query. While two of the seven suggestions I made - Alinea and North Pond - are above the stated price target (and might be suitable for the birthday dinner), the other five fit into his/her stated $20 price target.