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Valentine’s Day: Chicago 2020 Events

When it comes to Valentine’s Day events, Chicago goes above and beyond the usual date night. Whether you’re single, attached, or have kids, you’ll find something worth the trip into The Windy City. Check out our favorite events to create your super-special Valentine’s Day: Chicago 2020 edition.

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!

Where: 233 S Wacker Dr. Chicago, IL 60606

When: Mon-Fri at 8:00 a.m.

Breakfast-on-the-Ledge Valentine's Day: Chicago 2020 Events

Chicago Odyssey Valentine’s Day Dinner Cruise

Take date night to the max for Valentine’s Day with a Chicago Odyssey cruise! The Chicago skyline is a perfect backdrop for this gourmet yacht cruise along Lake Michigan. You’ll enjoy the rooftop lounge, and then sit down to a 3-course dinner that’s prepared on board by top chefs using only fresh ingredients. Dinner is followed by coffee and tea, plus musical entertainment from the onboard DJ. For a midday date, check out the Odyssey Lakefront Valentine’s Brunch Cruise!

Where: Navy Pier, 600 E Grand Ave, Chicago, IL 60611

When: February 14, 15 & 16th at 7:00 p.m.

The Dinner Detective Murder Mystery Dinner Show

If you and your date are drama and/or mystery story fans, you should really check out the Dinner Detective. They put on live murder mystery shows all year, but this Valentine’s Day edition is perfect for a special date night. As you and your fellow audience members sit down to a 4-course plated dinner, you won’t know which audience members are actually actors. Anyone in the room can end up being part of the show, including you or your date!

Where: 165 E. Ontario St, Chicago, IL 60611

When: Friday, Feb 14, 2020, from 6 to 9:00 p.m.

The Universal Sole Valentine’s Trail Challenge

The Universal Sole running store offers a laid-back trail run for the whole family and all ability levels. As Chicago’s first running store to bring trail racing to the Chicago running community, they offer runs on some of the city’s most beautiful trails. Enjoy beautiful Schiller Woods in winter on the 4.2 mile trail run, and then refuel with Clif Bars, bananas, and apples at the finish. For your real post-race reward, stick around for Will’s Famous Chili and brews from Odell Brewing Craft Beer!

Where: 1341 West Fullerton Ave. STE 526, Chicago, IL 60614

When: Saturday, February 8, 2020 at 9:00 a.m.

Valentine’s Day Snow and Ice Dyeing at Lillstreet Arts Center

Learn how to use snow and ice as a unique dyeing technique. In this “Date Night” at Lillstreet Arts Center, You’ll experiment with abstract patterns and color combinations to create your own scarf and dish towel, but feel free to bring your own additional items made of cotton, rayon, or silk. This one-day cass is a perfect way to dive into arts and crafts with a friend or Valentine at one of Chicago’s oldest art co-ops!

Where: 4401 N. Ravenswood Ave, Chicago, IL 60640

When: Friday, February 14, 2020 from 6 to 9:00 p.m.

Explore More Chicago Special Events with Skydeck! 

Don’t hesitate to contact our team if you’d like to learn more about Valentine’s Day events in Chicago, or other exciting events throughout the year. We can answer any questions you might have about unique Chicago happenings and holiday celebrations. You can also take a look at the events happening at Willis Tower Skydeck!