Where to Go for Valentine’s Day in Chicago, 2024?

Valentine's Day

There are thousands of perfect Valentine’s Day restaurants in Chicago and hundreds of Valentine’s Day Events in Chicago. While you may find yourself lucky to live in a city with so many options, that blessing can also be a curse, as it’s easy to get overwhelmed by all of your choices. At Skydeck Chicago, we’ve put together a slim selection of classic ways to celebrate Valentine’s Day in Chicago to help you narrow your options to a few great ideas sure to make your night one for the books. 

Valentine’s Day Events in Chicago 

From the best Valentine’s Day restaurants to the best Valentine’s Day in Chicago activities, check our top four picks below to start brainstorming about the biggest date night of the year: 

Breakfast in the Sky at Skydeck Chicago

Breakfast or pie at the top of the Willis Tower makes for a special date any time of year, but we think a Valentine’s Day date might be best of all! If you can’t get away for the evening, how about a romantic breakfast together? You’ll enjoy the quiet of the 103rd floor before The Ledge opens to the public and a catered menu by The Metropolitan Club. Book your table early for Valentine’s Day morning!

Khmai Cambodian Fine Dining 

One of two Cambodian restaurants in the city, Khmai offers a unique twist on Cambodian cuisine. This reservation-only, fine-dining restaurant pairs authentic Cambodian cuisine with truly a top-rated, fine-dining ethos. In essence, enjoy Cambodian food as prepared by an auteur chef. And after your meal, head over to Ward Eight on Howard St. for some of the best cocktails in town. 

Ice Skating Downtown

There are two exceptional places downtown where you and your date can ice skate in the glow of the skyline. The Millennium Park Rink is right below the bean, inexpensive, and just down the street from dozens of restaurants and bars. The skating ribbon at Maggie Daley Park is also an exceptional choice, as it features a quarter-mile-long trail that can only be traversed by ice skate. The path winds through all kinds of features of the park and is just below a dense thicket of several of the tallest buildings in the city.

Chicago Botanic Garden Orchid Show 

Yes, the Chicago Botanic Garden is technically located in Glencoe, a suburb about 10 or so miles north of the City. That said, all the suburbs on the North Shore are gorgeous, and the Chicago Botanic Garden is the pinnacle of all the beauty offered in this neck of the woods. Right around Valentine’s Day, the Chicago Botanic Garden features an exhibition with 10,000 orchids in full bloom. It’s certain to be a romantic night, and there’s no shortage of fine dining opportunities and cocktail lounges on the North Shore. 

Plan a Visit to Skydeck Chicago! 

What could be more romantic than looking out at the entirety of Chicago, four states, and all of southern Lake Michigan with your significant other? Plan a visit to Skydeck Chicago for a magical Valentine’s Day in Chicago, but first, learn more about the Skydeck Chicago experience