My Best Friend’s Wedding (1997)
Treat yourself with a stay at the Drake Hotel, the iconic hotel featured in the classic rom-com “My Best Friend’s Wedding.” The ever-so-posh Drake Hotel, located along the Magnificent Mile, is where the movie’s main character Julianne (Julia Roberts) stayed while plotting to ruin her BFF’s wedding. While there is still no smoking allowed on non-smoking floors (true rom-com enthusiasts will get the reference), the Drake offers incredible views of Lake Michigan from their luxurious suites and an unbeatable tea room experience at the Palm Court - perfect for celebrating Valentine's (or Galentine’s) Day!
The Break-Up (2006)
Start off with a meet-cute like Gary (Vince Vaughn) and Brooke (Jennifer Aniston) in the popular flick “The Break Up.” Take a stroll alongside the famed Wrigley Field. Then, tour the city on a double decker bus: While there might not be enough time in one weekend to take Chicago by air, land and sea, a double decker bus tour is a fun and convenient way to learn the history of the city. Plus, the tour guides are always entertaining, just like Gary. Tours operate as “hop on hop off” — perfect for exploring the city at your own pace. Tours arrive every 30-45 minutes and tickets are less than $45 per adult and less than $30 for kids.
Drinking Buddies (2013)
Sip on your new favorite beer on a tour of Revolution Brewing: In the indie romantic comedy “Drinking Buddies,” the movie’s main characters, Kate and Luke (Olivia Wilde and Jake Johnson), work at Revolution Brewing located in the Logan Square neighborhood. Revolution Brewing is now the largest independent craft brewery in Illinois. Beer devotees come from all corners of the globe to experience their brewpub and taproom, where they produce dozens of beer styles to quench every conceivable thirst—IPAs, porters, pilsners, Belgian-style, pale ales and barrel-aged beers. Now part of the Illinois Made program, Revolution Brewing offers tours of their 90,000-square-foot eco-friendly space, powered by over 200 solar panels that save over 50 tons of greenhouse gases annually. It’s the perfect Valentine’s Day experience for the beer-lover in your life.
High Fidelity (2000)
Experience the city’s most iconic entertainment venues Music Box Theater & Green Mill Cocktail Lounge: Esquire once referred to “High Fidelity” as the “truest Chicago movie ever,” and with filming locations like Music Box Theater and Green Mill Cocktail Lounge and set in the hip Wicker Park neighborhood, it’s easy to see why. Spend a fun-filled Valentine’s weekend catching a film at Music Box Theater—a historic single-screen movie theater in Chicago’s Southport Corridor area known for showing cult classics, foreign and independent films. Following the flick, stop by one of the city’s most famous jazz clubs, Green Mill Cocktail Lounge. This Prohibition-era club in the Uptown neighborhood has a storied-speakeasy past where you can take in some of the best jazz the city has to offer - just like John Cusack in the movie.
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