Four of Chicago’s Most Romantic Valentine’s Day Spots

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With hundreds of intimate restaurants and bars, rooftop retreats, and stunning skyline views, Chicago is home to many of the most romantic settings in the country. Couples planning a limo ride and a night on the town for Valentine’s Day have plenty of options in the Windy City. Here are four of the city’s most romantic Valentine’s Day spots.

The Rooftop at Cindy’s

A two-person dinner table next to a large window

Perched atop the Chicago Athletic Association Hotel, Cindy’s is arguably the city’s best rooftop spot. Boasting gorgeous panoramic views of Lake Michigan, Millennium Park, and the Art Institute of Chicago, Cindy’s is a great place for couples to cozy up and enjoy the scenery. Their brunch, lunch, and dinner menus rotate seasonally, and Cindy’s also offers award-winning cocktails and a dynamic wine selection.


Goosefoot takes intimate dining to the next level. Seating only 24 guests at a time, this Michelin-approved restaurant in Lincoln Square serves a multi-course tasting menu blending traditional French techniques with modern culinary artistry. Goosefoot is BYOB, so couples should remember to pick up a nice bottle of wine before dining.

Chicago’s West Loop Neighborhood

The West Loop neighborhood used to be the city’s meatpacking district, but today it’s a mostly tourist-free destination for adventurous dining. Known as “Restaurant Row,” the West Loop area is home to many up-and-coming restaurants. Couples can spend the evening exploring the neighborhood’s eateries, patios, bars, and romantic street scenery.

Geja’s Cafe

Geja’s Cafe is perfect for couples searching for a classically romantic spot for Valentine’s Day. This Lincoln Park restaurant’s intimate, candlelit atmosphere is accented with the sounds of live Flamenco guitar music. Geja’s Cafe specializes in fondue, so arrive prepared for an intimate evening of decadent cheese and chocolate selections.

No romantic night out in Chicago is complete without luxurious limousine service. Echo Limousine offers several vehicle options for exploring the city, plus a variety of other car services, including corporate travel, prom transportation, and special event limo services. Call or text (773) 774-1074, or book online to reserve a limo for your next romantic evening in Chicago.

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