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Apr 22, 2013 03:46 AM

Dive bars, holes in the wall, quirky places full of character in Chicago

Hi all,

Before I start, I need to put this thread into context. I am an Irish guy living in London and have just returned from a trip to the South (Tennessee, Georgia and South Carolina) where I ate at some great restaurants and sampled some really cool dive bars with tons of local flavour. However, the last leg of my trip was in Buckhead and it was a big let down. Just not the type of places you will find anything that doesn't have generic food, be it high end or low end - and the bars didn't have any character either.

So later this year I will be in Chicago for 8 nights. I want to stay in a neighbourhood where I don't have to grab my vehicle from a multi story carpark every time I want a meal. I want to either be able to walk everywhere or at least have a reasonable trip on public transport. i will be happy to get a taxi or make a special effort to go to a place that is highly recommended though - no doubt about it. Just don't want to have to do that every single night.

What I am looking for is:

What is Chicago famous for? Hot dogs and deep dish pizza? I love both - especially hot dogs - I also like steakhouses but then I should be able to find info on those fairly easily. Throw me some recommendations! Anything else / be it cuisine type or establishment type unique to Chicago or particularly well done in Chicago? Where are the "institutions"? I am not afraid to go high end but there must be a reason to do so. I live in London and I can get the best Michelin star dining in the world here - Michelin star places are the same the world over. But that is not to say I don't look for quality - at whatever price point it is at. I'm also not really looking for "modern interpretations of".

Also: what about either dive bars or other characterful bars where you can sit down and have a good chat with the bartender and other patrons. I tend to like hipster joints as usually they are welcoming for the out of town traveller - but I do like to get some banter from some grizzled locals - "been here all my life" types. Does that make sense?

So I am also asking for recommendations for where to stay to have access to some of the best of the above types of food. Places that will be buzzing at night and not just with tourists who have been out all day doing loads of shopping - I'm not all that interested in shopping to be honest. A final point is I am single and 33 - so having the potential to meet up with women would be good - if not necessarily the driving factor behind my decision to stay in any one area or frequent any one establishment.

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    1. >> What is Chicago famous for? Hot dogs and deep dish pizza? I love both - especially hot dogs - I also like steakhouses but then I should be able to find info on those fairly easily. Throw me some recommendations! Anything else / be it cuisine type or establishment type unique to Chicago or particularly well done in Chicago?

      Deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches, and creative contemporary Mexican cuisine are all standouts that Chicago is famous for and/or are relatively unique to Chicago. Lou Malnati's is a great place for deep-dish, and has locations all over the city and suburbs. There are hot dog and Italian beef places all over the city so it depends on which neighborhood you wind up in. You can get a feel for Chicago neighborhoods for food in the discussion at See below for contemporary Mexican recommendations.

      There are also ethnic neighborhoods where you can experience food from specific nationalities. These include Indian/Pakistani food on Devon between Sacramento and Western; Vietnamese food along Argyle near Broadway; Greek food along Halsted west of the Loop; and Chinese food in Chinatown around Wentworth and Cermak (22nd St).

      For bars, including dive bars, you might want to check out the discussion at I'm sure others will have more comments; danimalarkey is our resident expert on the subject.

      Someone else recently posted that they will be in Chicago for 36 hours on a first visit to Chicago. Here's what I posted there ( ) and maybe it will give you more ideas (it was asked by someone staying near the Mag Mile, so directions are given from there):

      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. 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 - 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.) 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. Henry, 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). 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.

      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. I would suggest basing yourself at a bed-and-breakfast in Wicker Park, since you find hipster joints friendly to out of towers, which I think you will find to be true here as well. I sent friends to House of Two Urns last year and they enjoyed it.
        Random suggestions based on your post:

        Hot Doug's at about 2 p.m.; a local institution for upscale hot dogs (avoid during lunch rush; also, closes at 4 p.m.)

        Spend a day at the Art Institute and have lunch at Terzo Piano in the contemporary wing. Walk through Millennium Park afterwards.

        Toon's for conversation with locals; have chicken wings and whatever is on the specials board

        Delicious cocktails at The Violet Hour and/or Scofflaw's; not divey but highly enjoyable

        Chinatown Square Mall in Chinatown

        Argyle Street for Vietnamese

        Wicker Park/Bucktown and nearby:
        The Bristol
        Owen & Engine
        Whistler (bar)
        Bang Bang Pie Shop

        Also consider spending a day at the Museum Campus, where there is a natural history museum, an aquarium, and a planetarium. Hike back to Michigan Avenue for decent Irish fare at The Gage, or hit Heaven on Seven for Cajun

        North Michigan Avenue is the tourist mecca and can turn into a Buckhead redux if you don't choose wisely. But there are several good places around there that should pop up in some of the threads already mentioned.

        5 Replies
        1. re: camusman

          >> Hot Doug's at about 2 p.m.; a local institution for upscale hot dogs (avoid during lunch rush; also, closes at 4 p.m.)

          Beware, the lines at Hot Doug's - typically 90 minutes or longer - are not just during the "lunch rush". I've seen them even longer when I've left after 2 pm than when I've arrived at noon.

          You can get Chicago-style hot dogs all over town, so there's no need to endure the long lines at Hot Doug's just for those. If you want more unusual sausages (encased meats), consider Franks 'n' Dawgs in Lincoln Park, where you won't have to endure long waits.

          1. re: nsxtasy

            I am a Doug's loyalist FYI. The line can be managed if you time your visit to about 11:30am. or 3.

            You might also consider staying at Longman and Eagle.

            Close to the blue line that could get you to a few places to hit up.


            1. re: BSpar

              Yes, Briansy, Hot Doug's is worth the effort. You asked about Chicago "institutions." This is definitely one of them.

              1. re: BSpar

                I just want to echo BSpar's suggestion for Longman & Eagle for a place to stay. Rooms are very comfortable and stylish and well-located, in terms of dining/drinking/public transportation. Not to mention the fact that Longman & Eagle is precisely the kind of bar where you can talk to bartenders and regulars while enjoying one of the best bar programs in the city (and the food is pretty good, too).

                If you're in town for so long, I'd consider splitting your stay between L&E and the other hotel you've found. You'll get a vastly different experience staying in Logan Square (the neighborhood where you can find L&E) compared to downtown. Longman puts you within spitting distance of a host of great options:
                Lula (restaurant)
                Scofflaw (more bar than restaurant but the food is still great)
                Yusho (restaurant with a small bar area)
                Fat Rice (restaurant)
                Helen's Two Way (dive bar)
                Whirlaway (dive bar)
                The Owl (dive-ish bar)
                Cole's (dive-ish bar)
                Revolution (brewpub with great food)
                Billy Sunday (cocktail bar)

                And then you're just a short L ride to Wicker Park/Bucktown which is another great neighborhood, as well.

                1. re: danimalarkey

                  Also in Logan Square is Jam, one of Chicago's very best breakfast/brunch-focused restaurants.

          2. Guys: I think I've found the area I am looking for - within 3 miles of "Hotel Sax", I have 89 dive bars - granted only about 10 of them look like really cool places - many of them are restaurants with a licence etc- but this looks like a great part of the City t hang out and meet people am I right??


            Combine some of these with Hot Doug's, Frank'n'Dawg, Deep Dish pizza, La Frontera, a Steakhouse (maybe Gibson's?) and a couple of fine dining restaurants like Sable and I am in great shape I think.

            6 Replies
            1. re: briansy

              I happen to like the lodge, richards, and really enjoy Rossis. But they are DIVE bars.

              1. re: BSpar

                Did I not ask for dive?!! There appear in these 89 to be proper dive and a bit more sanatised dive but still with character - I'm guessing this hotel is in a great spot for both bars and restaurants?

                1. re: briansy

                  Indeed, as nsxtasy says, Hotel Sax is near tourism central on N. Michigan. As an example of the type of neighborhood this is, Donald Trump's Tower is two blocks away.

                  But that does mean you are in a great location for restaurants. Two that are very close to the Sax that you can add to your list are Naha and Sunda.

                  1. re: briansy

                    Chiming in from the female and hipster bar lover perspective: you're not going to find much of the latter near Hotel Sax, but you'll find a decent amount of the former.

                    I'd second a handful of the above bar suggestions as good places to meet people or at least be entertained by them: Cole's, Scofflaw, the Whistler. Hop on the blue line, get off at California/Logan Square, or jump in a cab and head to West Town. Depending on your interests, you might like Empty Bottle or the California Clipper.

                    1. re: allieha

                      Allie - very useful - do you have an email address I can contact you on - I want to pick your brain on something! Alternatively, you can get hold of me on

                2. re: briansy

                  Just FYI, Hotel Sax is in an area called River North, just north of the Loop (Chicago's historical and commercial downtown), and a short walk from the "Magnificent Mile". This is Chicago's premier district for hotels, restaurants, and shopping. Many of the restaurants and bars are pricy; many others are not. And yes, there are many, many such places in a compact area, within walking distance. Since this is where many hotels are, this is also the area with the highest concentration of visitors from out of town, although there are also plenty of nearby residential high-rises where locals live.

                  For great steaks, I would recommend either David Burke's Primehouse or Chicago Cut Steakhouse. Both are within a few blocks of Hotel Sax.

                  Also, I love Sable, but I would not refer to it as "fine dining"; it's a casual chef-driven restaurant with terrific, moderately-priced food in a small plates format, and great craft cocktails from some of the best bartenders in the city.

                3. I live in River North, really like a great meal, but also really enjoy dive bars or at least neighborhood "joint". Places that I frequent in order of closest to Hotel Sax.
                  - The Boss Bar - Clark and Hubbard
                  - Shamrock Club - Kinzie between Wells and Franklin
                  - Green Door - Orleans and Huron
                  - Club Lago - Orleans and Superior - Italian food too
                  - Richards Bar - EITHER W Grand OR N Milwaukee

                  Something you will find in Chicago that is rare elsewhere is the plethora of neighborhood bars. Everywhere you go throughout the city there will be bars on the corner and you'll be comfortable just walking in.