It’s easy to fall into a comfortable routine while dating in Chicago: Cozy up at a romantic restaurant, grab drinks at your local dive, maybe go to a movie if you’re feeling super wild. And while Chicago dives do have a certain romance to them, routine is boring, and god forbid you come off as boring. We’ve collected some easy, low-key dates that are far more likely to spark romance than just drinking the awkwardness away does. Plus, if you’re going to date your way through Chicago, you may as well get to know the city while you’re getting to know your future beau.
Romantic date ideas in Chicago
The Second City's sketch revues are consistently hilarious, so there's no surprise this comedy institution is a point of pride in Chicago. This is a total bullseye date—the performers have the ocassional off-night, but in all likelihood you'll laugh, have some drinks, feel pushed a little bit out of your comfort zone, then laugh some more. Even if you know nothing about improv, this is a great date spot for any stage of a relationship.
The Music Box won't be screening the latest Hollywood blockbusters, but that's not a bad thing. This theater offers a constant stream of indies, documentaries and old classics that qualify as one of the most diverse selection of films in Chicago. You and your date won't have to be film nerds to find something new to like that will set you apart at your next cocktail party. Swing by the Music Box's lounge for a drink afterwards so you won't have so say goodnight so fast.
Walk through a tiny slice of tropical paradise among towering palms, colorful flowers and gorgeous ferns with that special someone. The conservatory is one of the finest and largest of its kind, not only in America, but the entire world. This system of greenhouses is home to more than 600 species of plants and nearly 120,000 specimens in total. The sheer variety of plants makes this a great opportunity to knock out a little window shopping before heading to the plant store while enjoying beautiful surroundings you quite literally can find nowhere else.
The Civic Opera House isn't exactly a looker on the outside, but the interior is positively dazzling. The stage is home to one of the country's most respected opera companies, the Lyric Opera, and also plays host to the occasional concert, with names such as David Byrne, Andrew Bird and Wilco having performed in the past. We wouldn't suggest this one as a first date, but if you're looking to spark up your relationship, a night at the opera never hurts.
Okay, so this one is technically just going to a bar and drinking, but there's definitely a romantic appeal to bars with fireplaces. And thanks to our 11-month long winters, Chicago has enough bars with fireplaces to go around. Nestle in with your date, a cocktail and a blazing fire, and we guarantee you won't want to leave anytime soon.
Warning: You might view the Chicago skyline from this highly underestimated southern beach and not want to leave. Perfect for sunbathing in the summer, picnics in the fall and icy sojourns in the winter, it's also accessible from the Lakefront Trail, making it great for couples who like to stay active and exercise outdoors all seasons.
Head down to Jackson Park and you'll forget you're even in Chicago. A site of the World's Columbian Exposition of 1893, Jackson Park is also home to the Osaka Garden, one of the most picture-perfect spots for taking a stroll in all of th ecity. The park was designed by one of the landscape architects who designed New York's Central Park and looks like it's straight out of a Japanese woodblock print. Why go to a museum when you can go inside a piece of art?
Andersonville is one of Chicago's most charming neighborhoods, with tons of shopping (and exceptional vintage shops), low-key bars and some of the best Chicago restaurants. Clark Street is made to be wandered up and down—it's perfect for window-shopping, stopping in somewhere for a snack or a drink and doing more window-shopping. Just try not to draw the obvious parallels between wandering aimlessly down the street and the current state of your love life.
The Riverwalk is still a pretty new commodity, so there's a good chance your date hasn't spent time down there yet. The huge strides Chicago has made along its backwards flowing river have created a date spot that doesn't fail to disappoint, with more and more great spots to stop for a glass of wine or bite to eat along the way. Venture down there on a Saturday or Sunday afternoon and you'll remember that the Loop is actually pretty gorgeous.
Explore the whole neighborhood while you're at it, but this vast green space on the West Side is one of the dreamiest spots in the city. Designed by William Le Baron Jenney in the mid-1800s and enhanced several years later by Jens Jensen, Humboldt Park was once the nation’s greatest public park, boasting acres of Prairie-style gardens, grazing animals and a meandering river scene. Though the animals are long gone, the park still offers extensive rose beds as well as tennis courts, baseball fields and bike paths. Plus, there's an inland beach, so bring your swimsuits!