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Some of the best options in the city include the Dan Ryan Woods, Palmisano Park, and Caldwell Woods, while the burbs offer an array of hills like James Park in Evanston and Riverside’s Swan Pond.
The stylish, recently revamped Logan Theatre is always a solid date choice, but becomes even better in winter thanks to their “Jolly January” late-night movie series.
Chicago may not be known as a gambling mecca per se, but the city is surrounded by a variety of casinos that can make for a fun alternative to the standard dinner-and-a-movie routine.
Hit up suburban casinos like Rivers Casino, Harrah’s, and Grand Victoria, or ride the shuttle to places like Horseshoe Hammond and try to get lucky in more ways than one.
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.
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.
If your relationship can survive a clown class, it can survive anything. No matter where you are in the city, it’s guaranteed to be warmer in the Garfield Park Conservatory, which is brimming with lush plant life year-round.
After a winter of staring at gray skies and barren concrete, the vibrant greenery is a sight for sore eyes.
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).