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Chicago - Suggestions Needed

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    Chicago - Suggestions Needed

    So I'm heading to Chicago for a small holiday and am looking for suggestions. I'm looking for jazz/blues bars, good burger joints, places to see, and of course #menswear places to go.

    Thanks.

    #2
    http://butcherandtheburger.com/

    Architectural boat tour (if the weather is decent)
    Chicago Athletic Association (and Cindy's, their rooftop bar), https://www.chicagoathletichotel.com/

    http://greenmilljazz.com/

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      #3
      If you are downtown for the Architectural boat tour (highly recommended) and the CAA on Michigan Ave, you can hit the Jazz Showcase (806 S. Plymouth Ct.) or Buddy Guy's Legends blues club (700 S Wabash Ave) for music rather than head back up north to the Green Mill.

      For burgers I happen to like Good Eats, also downtown (22 S. Wabash) or head to the West Loop for the super popular burger from Au Cheval (800 W Randolph St). For outstanding Korean fried chicken, go to Crisp on the north side (2940 N. Broadway), then walk south to the nationally-ranked Molly's Cupcakes (2536 north clark street).

      Now I'm hungry. Chicago may get a lot of stuff wrong, but they absolutely do food and music right.

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        #4
        Thanks! And yes, I've heard the architectural boat is great. I'm planning on signing up for it.

        The tips on the bucher and the burger, and the jazz bar are good too. I've been looking online for jazz bars, but all of the recommendations are for the same bars. I fear they will be overly touristy and expensive. The more authentic the bar and jazz, the better.

        I've been hearing good things about Chicago and am definitely looking forward to the trip.

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          #5
          I'll second the architectural tour on the river. It's such a perfect way to see the city.

          Andy's Jazz Club on Hubbard can be good, depending on who's playing. It's a pretty traditional format - tiny tables, 2 different bands plays 2 sets starting every 2 hours. Andy's has food but I can't vouch for it; it's right next door to Shaw's Crab House (great traditional seafood joint). Shaw's also has jazz in their oyster bar / lounge sometimes if you just want a little taste.

          Also live music downstairs at Pops for Champagne is usually good, and the people watching in the main bar can be epic. No cover charge Sunday - Tuesday. http://popsforchampagne.com

          I'm local and I live downtown, so feel free to PM me with last-minute questions.

          For menswear, you should definitely take a quick trip to Optimo hats. Even if you aren't in the market, just take a look around. They used to be on the South Side and now have a downtown showroom at Jackson and Dearborn. https://optimo.com/contact-downtown

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            #6
            The obligatory suggestion for burgers is Au Cheval. In my opinion it lives up to the hype. The wait can be very long, but there are several bars nearby where you can get a drink during your wait. Kuma's and Lockdown both have good 'gourmet' style burgers. I'd also suggest getting an Italian Sub from J.P. Graziano's.

            I second the architectural boat tour if the weather is nice, you'll get views of the city you wont see anywhere else and they are actually informative. I also second the Green Mill. It's been open for 110+ years and has Prohibition era mod connections.

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              #7
              [MENTION=2576]Furious Styles[/MENTION] reminds me - If you really like jazz, it doesn't get more authentic than jazz showcase. It's all about the music there. Of course, it would depend on who's playing and your taste but Joe Segal has kept that place going through I don't know how many locations. When they were at the Blackstone Hotel, I saw Buddy Rich and Louis Bellson there. Last show I saw was David Sanchez.

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                #8
                On menswear you have to visit one of the Paul Stuart stores. Its above the dappered price range, but definitely worthwhile visiting to browse.

                I went to Marchesa without knowing much about it after landing late and really enjoyed it.

                And, its expensive, and you may not be able to get a reservation, but the Aviary cocktail bar is worth it I think - others may disagree. It is certainly an experience.

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                  #9
                  You guys are making me want to visit Chicago. Is there any particular time of year that stands out as the best time to visit? I know the winters can be brutal.

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                    #10
                    I'd say summer or fall. The winters are indeed brutally cold, but they don't generally get a ton of snow. Spring that far north is always a crap shoot - could still be cold in late April or even May, with the trees still bare. Because of the long cold winters summer features constant neighborhood block parties, street festivals, etc. - basically they make the most of it because it's finally nice outside. Fall is also nice but likely to be over about a month earlier than, say, the latitude of the Mason Dixon line. I don't really mind Chicago winters but then I grew up in Michigan.
                    “Clothes make the man. Naked people have little or no influence on society.” – Mark Twain

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                      #11
                      Chicago is best in early summer or early fall. Avoid peak heat, but still nice/sunny, but also avoid the windy/bitter winter. Bonus points if you can make Wrigley for a game and hang out in Wrigleyville a bit before/after (if baseball / drinking are to your liking).

                      I don't have any specific reco's as it's been a rather long time since I lived there for 6 months, but it's a pretty fun city.

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                        #12
                        These are all fantastic suggestions. Thank you!!

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                          #13
                          The best time to visit Chicago is between June and October (I live in the City).
                          Best pizza? Pequods on Clybourn
                          DMK burger is amazing (owned by the Morton's)
                          Blues/Jazz bars are few and far in between anymore.
                          People love the architectural tour (I've never been on it)
                          Menswear? There is a SuitSupply and Bonobos at 900 North Michigan...lots of high end clothiers on Oak Street.
                          Night out? STK or Gibson's Italia

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                            #14
                            Love all these suggestions, and props to [MENTION=18448]SteelerBill[/MENTION] for mentioning Pequods.

                            We should all go bumrush the Bonobos and Allen Edmonds stores one day.

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                              #15
                              I would also hit London House rooftop....amazing place.

                              https://www.youtube.com/watch?v=yEm7pYumQnA

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