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Three Dots and a Dash and Lost Lake are among the most famous in the city, but alarmingly fun times can also be had outside city limits at popular suburban hangs like Hala Kahiki and Chef Shangri-La.
A bookstore may not sound like the most exciting date in the world, but places like Lincoln Park’s Kibbitznest are tailor-made for summer.
The Globe Pub is the granddaddy on the scene, Reggie’s is a great Monday night spot for sports and music trivia, and Simone’s is a standout choice for Q&A trivia Tuesday nights.
The stylish Logan Theatre or Music Box Theatre is always a solid date choice, but becomes even better in spring or summer when you can enjoy an ice-cold pre- or post-movie cocktail at the bar inside..
The lake isn’t the only waterfront in Chicago, though.
If you’re in the Loop anyway, pick a spot along the quickly-developing Chicago Riverwalk to grab a drink and a bite with your date.
Luckily, Chicago is brimming with lively bowling options like Diversey River Bowl and Southport Lanes.
The obvious (and gorgeous) choice would be to ride along the Chicago Lakefront Trail, but the 606 is a better choice if you want to stop for food and drinks along the way. ) Chicagoans are lucky to live in a two-team baseball town, and everyone ought to take advantage.
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.
The lake is kind of an obvious date spot, whether you’re a Chicago native or tourist on Tinder, but that doesn’t make it any less fun.
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.