A Rom-Com Getaway in Chicago

Spend your Valentine’s weekend recreating your favorite romantic comedies that were filmed in Chicago.

My Best Friend’s Wedding (1997)

Treat yourself with a stay at the Drake Hotel: For an unforgettable weekend getaway, stay at 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-comenthusiasts will get the reference), the Drake Hotel 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)

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 Chicago. Plus the tour guides are always entertaining just like Gary (Vince Vaughn) in the popular flick, “The Break Up.” 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.

Related Reads:

Chicago’s Best Bars for Whiskey Lovers

Chicago’s Best Bars for Whiskey Lovers
in Arts & CultureEat & DrinkChicago

No matter if you prefer your bourbon neat, on the rocks or in the form of a clas...

Secret Service

Secret Service
in Eat & DrinkChicago

The covert legacy of Chicago’s Prohibition-Era speakeasies carries on in night s...

A Whirlwind Weekend in the Windy City

A Whirlwind Weekend in the Windy City
in ChicagoActivitiesArts & CultureFood & Beverages

Mix and match a stop from each category to create your own must-do lineup. The b...

Enjoy Illinois Magazine

Enjoy Illinois Magazine

Find unexpected ways to enjoy Illinois in this biannual magazine that explores every corner of the state. Each issue offers a mix of travel stories, stunning photography and timely trip ideas that make the most of each season.

Order a Copy

Order a copy of Enjoy Illinois and also receive the Illinois State Park Guide and an Official Highway Map.

Order Print Version
Grab a Digital Copy

Read Enjoy Illinois magazine online or download the PDF and start exploring trip ideas around Illinois.

View it Online Download PDF

Send me Enjoy Illinois Magazine

Get inspired by top travel stories, and discover even more reasons to #EnjoyIllinois.

Order a Copy!