Creative dating idea
So bundle up and get cozy with these can’t-miss winter date ideas.Second City is, of course, the granddaddy of comedy-themed date nights, but good times can also be had for fewer dollars (and fewer people from Iowa) at indie comedy venues like the Cornservatory or regular stand-up nights like Timothy O’Toole’s “Comedians You Should Know” (see full list here).
A bookstore may not sound like the most exciting date in the world, but places like Lincoln Park’s Kibbitznest are tailor-made for winter.
Hubbard Inn offers two fireplace lounges on two floors, while Moody’s Pub is a romantic medieval castle-like favorite. Show off how cool you are with your in-depth knowledge of Chicago’s secret bars.
Since knowing that the mural on Damen in Wicker Park opens up to Violet Hour is no longer considered insider information, Booze Box is a sexy bet, The Office is uber-swank, and East Room is not technically secret but does lack proper signage.
You can also shoot bows and arrows in Humboldt Park at Archery Bow Range Chicago or chuck axes at the wall at joints like Bad Axe (both are /hour for walk-ins, with cheaper rates for groups and other options too).
There is perhaps no easier winter date than at one of Chicago's fine tiki bars: immediately fun, warm, and cozy, the only way you can screw this up is to start talking politics.This may be a pricier option, but the real question is: Can you really handle 10 hours in the car together?