7 Date Ideas for Valentine’s Day in Chicago

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February 2, 2018

Valentine’s Day is just around the corner, and luckily, so is Chicago Trolley and Double Decker Co., ready to transport you to Chicago’s hottest tourist and shopping destinations. If you’re planning a romantic getaway to the Windy City this Valentine’s Day, we’ve taken the stress out of planning the perfect date and compiled a list of 7 stellar activities – some traditional and some off-the-beaten-path, to impress the one you love.  


An Evening at Navy Pier

[Image Credit: Navy Pier]

There’s no better place to spend Valentine’s Day than this world-class tourist destination in the heart of Chicago. Book a Hop On, Hop Off Tour with Chicago Trolley, and after enjoying an incredible day of sightseeing and shopping around town, end the night at Navy Pier.

There’s endless fun to be had along the Pier, from romantic, world-class dining at Riva Crab House, to seeing live music at the Aon Grand Ballroom or a show at Chicago Shakespeare Theater. And don’t forget a ride on Centennial Wheel—complete with heated cars—for a breathtaking view of the Chicago skyline. With this classic Valentine’s Day date, you can’t go wrong!


A Dinner Cruise Aboard the Odyssey

[Image Credit: Odyssey Cruises Chicago]

Roses are red, violets are blue, how ’bout a date on the water for two?  This Valentine’s Day take your love on a cruise aboard the Odyssey. You’ll not only experience ultimate luxury and unique views of Lake Michigan, you’ll also have a first-class dining experience and dance the night away to live music. Nothing says “romance” like a 3-course plated meal under the city lights. Trust us, this date will be hard to beat.


A Helicopter Tour of the City

Looking to take your relationship to new heights? We know just the thing! Experience a helicopter tour of Chicago with the Chicago Helicopter Experience Valentine’s Day special and see all of the city’s iconic sights from a birds-eye view. Get ready to look out over beautiful Lake Michigan, circle Willis Tower and John Hancock Center, soar above Millennium Park and more – all while indulging in gourmet chocolates and a champagne toast. These tours last roughly one hour and will be well worth your while.


Ice Skating

[Image Credit: City of Chicago]

Need a date idea as timeless as your love? Ice skating downtown is as classic as it gets. For a traditional ice rink opt for Millennium Park after dark, where you’ll find music, colorful lights and a breathtaking view of the Chicago skyline. If you’re looking to try something a little different go for the Skating Ribbon at Maggie Daley Park, with laps twice as long as traditional ice rinks. Oh, and don’t forget to grab some hot chocolate!

Tip: Millennium Park is a stop on our Hop On, Hop Off Tour!


Cupid’s Undie Run

[Image Credit: Cupid’s Undie Run]

If you’re in town the week before Valentine’s Day, you’re in for a treat. Take your love on a run they’ll never forget at Cupid’s Undie Run on February 10, 2018. Run a mile to raise funds for Neurofibromatosis research while competing for prizes like t-shirts and flasks. After the run, enjoy a party at John Barleycorn with drinks, food and music. This is the perfect date for couples who love to being active. 


A Spicy Dance Class

[Image Credit: Ballroom Dance Chicago]

You could always default to dinner and a movie this Valentine’s Day, but where’s the romance in that? Show your loved one how much you care with a night of dancing to make them swoon. Join Ballroom Dance Chicago for a spicy salsa dance class followed by a slowed-down, romantic rumba class. Expect sparkling wine, hors d’oeuvres and an evening to remember. 


Date Night at Ignite

[Image Credit: Ignite Glass Studios]

For the 6th year in a row Ignite Glass Studios will open its Hot Shop after-hours for a very special glass heart workshop for couples. You’ll have a chance to work alongside Ignite’s artists to collaborate in creating a beautiful and original glass heart of your own design. Couples are encouraged to come early or stay late to socialize and enjoy complimentary sparkling wine and chocolates to set a romantic mood for the evening.   


Whether you’re looking for a classic date night or feeling adventurous, there’s unforgettable options for every couple. And with our Hop On, Hop Off Tour, getting to many of these date night destinations is a breeze! Book your tour today, and experience the romance of Chicago in February the right way.