Here’s a particularly tricky aspect of being the “Chicago Travel Examiner” (a title that would totally hold water on LinkedIn and is not at all semi-arbitrary): if one leaves the city for an extended period of time, it is awfully difficult to keep a finger on the pulse of all things savvy and recommendable. Therefore, since this author is on tour for two months (and let it be noted that she is only being third-person pretentious because Examiner requests that we – I mean – she means – they – use only third-person to avoid sounding too blog-y).
Which is inconceivable, really.
So Chicago Travel is getting in on the latest trend: crowdsourcing. Kickstarters do it, contestants on Who Wants to Be a Millionaire do it – even Lay’s did it when they created those weird chicken and waffle-flavored chips (which proves crowd-sourcing doesn’t always work).
But not in this case. So here, decreed by legitimate Chicago residents, are suggestions for some of the best – or most definitive – offerings from the Windy City:
Chriskindlmarket: In most places, the Teutonic high holiday is Oktoberfest, but here, the Germans sufficiently recover from the beer hangover by late November in order to bring das magic of Christmas to life. Chriskindlmarket is an outdoor food and gift fair that Chicagoans officially use to herald the start of the holiday season. You can peruse handmade holiday decorations, nativities, toys, sweaters, candles and more from all over the world, all while drinking the market’s famous mulled wine. It’s pretty much like a globally representative version of the house from Miracle on 34th Street exploded and you get to explore while developing a nice little buzz. What more Christmas spirit can you ask for?
Improv Olympics: Everyone knows about Chicago’s Second City (you can get on the stand-up version of the indie bandwagon at Up Comedy Club), but they give just as good at arguably the second-most famous improv group in town, where four to ten shows are performed every single night. With cheap tickets, everything from long-form to musical improv, and themes ranging from “Improvised Star Trek” to “The Improvised Shakespeare Co.,” you can get your laughs with Kirk or the kings (although hopefully Shakespeare Co. stays away from the history plays - boresville). And if it’s called Improv Olympics, then the gold medal goes to TJ & Dave, who put on a one-act improvised play every Wednesday at the cabaret theater. News of their hilarity has traveled as far as New York, so while tickets are only $5, make sure to get them at least a week ahead.
Lake Shore Trail/Lake Michigan: Respect has already been paid in this column, but it came up twice in the poll and certainly deserves a repeat mention. It really is the best way to experience the spirit of the city without the distraction of rushing people – which sounds counter-intuitive, but hop on a bike or go for a stroll down the winding eighteen-mile path and it will all make sense. Instead of a panorama of buildings seen from across the harbor, the curve of the shore hugs the skyline in close – and nothing matches the imminence of those buildings paired with sparkling blue waves on a sunny day.
Museum of Science and Industry: Yes, you'll find it on the TravelZoo list, but this really is the sort of guidebook attraction that is worth a visit. Unlike most "interactive" museums, the interactive bits aren't just for children. It's like Disneyland for nerds, and endlessly fascinating. Go, and prepared to get giddy about science!
The Green Mill: Street cred just ain’t what it used to be. Nowadays, the brownie points towards your cool rating have to be gluten-free and made with organic, fair-trade chocolate. If this makes you want to drink (and you know it does), head to The Green Mill, arbiter of all that is old-school cool. Once a famous mobster hangout – if you get there early enough, maybe you can snag Al Capone’s booth – it now sets the bar for Chicago nightlife, with live jazz filling the lounge every night until at least four am. Kingston Mines is also worth checking out.
So whether you’re here for summer vacation or winter break, for a wild night or some ah, hard-core handicraft hunting, you can thank the locals for the inside scoop.
And that they haven't tried to feed you weird-flavored potato chips.
Special thanks to Caroline Baele, Rodman Bolek, Ashley Braxton, Stephanie Hansen, Nick Hogan, Kathryn Krause, Carmen Molina, Matthew Paul and Daniella Rukin for their contributions to this article!