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But is there anything more romantic than the 100-year-old theaters in the Loop Theater District, like the CIBC for you high-roller 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.
Be sure to hit up Montrose Beach on the North Side, South Shore Beach on the South Side or any of the other fantastic beach spots Chicago has to offer.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).Fortunately, comedy shows tend to be pretty cheap dates.There’s nothing more fun than Chicago in the late spring and summer -- especially when you get to share it with your main squeeze (or your side piece -- we’re not here to judge).The city offers everything from romantic walks along the beach to fancy indoor fun, like a performance in the Theatre District (hurray, air conditioning! No matter how you prefer to impress the guy or gal in your life, this list is chock-full of creative ideas for a date in Chi-Town.