greetings chicago forum!
i'm traveling to rockford for a conference next week and, as i've never been to chicago but always wanted to visit, tacked a few days onto the end of my trip to check out the city. i'll be arriving in town on a saturday night (two weeks from today) and staying through late afternoon that tuesday. as i'm in town for work, i'm traveling solo.
i'll be doing general touristy things during the day. i've been perusing these forums and doing other general research; i have a CityPASS so that may well fill my day time--along with the various tours i'm looking at (and places i want to eat!) but as a frequent solo traveler, i often struggle figuring out fun things to do in the evening. you know, after attractions close and tours end. this shouldn't be challenging in a major metro area, but for me it is, as i'm not a club-going type of person. i do not wear heels and i do not dance (unless i am outside and barefoot). i found what i thought was a great 'second city solo' article in the NYT from a few years ago, but apparently that reporter IS a club-going person. ha.
i much more jazz club. comedy club. even irish pub or sports bar. but it is often difficult to figure out where to go that being alone is not awkward. for example, i--like all other tourists--was considering a second city performance. i'm not sure if this would be awkward solo, however. i realize the seating is communal, which i don't mind (i am insanely outgoing). but i've been to things like that before where i was seated with not a couple of couples, but with one large group. THAT is awkward! (at a dinner theater event on a cruise ship, i was seated with a family of four--mom, dad, two small children, and me. i asked to be moved.)
so--what's a non-clubbing solo traveler to do in the evening in chicago? i'm staying downtown and will not have a car, but will be using public transport/taxis.
note: i'm arriving around 6pm on saturday night, meaning two of my nights that i have to fill are the most awkward nights--sunday and monday.
thank you in advance!