Valentine’s Day in Chicago

Valentine’s Day in Chicago

Love is in the air in Chi-Town, tourists and residents alike warmly welcomed into the cities chilly February cityscape during its most romantic day, Valentine’s Day!

Chicago is the perfect travel hotspot to cozy up with the one you love (or someone you just met) and keep warm as you explore a cultural mecca full of dazzling city lights, romantic culinary delights, and enough fun to last more than a couple nights.

Since this is considered an ‘off-season’ for travel in Chicago (low temperatures), this is also the perfect time to snag great deals on airfare and lodging, not to mention dinner and entertainment in the city. Any deal is a great deal in our book, and Chicago during Valentine’s Day is a really, really great deal!

November-March
Biting winds and freezing temperatures (daytime highs rest in the low 30s to high 40s, but wind chills can cause temperatures to drop into the negatives) deter faint-hearted tourists, leaving hotels and flights with plenty of vacancies. If you can stand the wintry weather, you'll find some of the lowest rates during this time. You can seek refuge from the cold in the city's museums, but if you're hoping to visit Millennium Park or shop along The Magnificent Mile, wear your warmest layers. - Source US News Travel. Read More
  • Average February 14th Temperature: 30 (F)
  • Average Flight Cost to Chicago in February: Average, though Hotel costs are quite below average.
  • Average Crowd Level in Chicago in February: Low

Okay, so it’s a great deal, it’s cold, and it’s romantic, but what can you actually do in Chicago on Valentine’s Day? Here are our top 10 choices for excellent Valentine’s Day dates in the Windy City!


  • Navy Pier - From excellent onsite eateries perfect for a rom
    Navy Pier Ferris Wheel Under Construction 2016 GT Staff

    Navy Pier Ferris Wheel Under Construction 2016 GT Staff

    antic dinner to an IMAX entertainment center for a show, Chicago's Navy Pier is a seriously underrated place to spend Valentine's Day. Once you are here you won't have to pay for parking anymore throughout the day or worry about public transportation, you can just spend the entire day exploring all that Navy Pier has to offer.The Crystal Gardens are excellent to sit and people watch, the shops are amazingly fun, and the Centennial Ferris Wheel outside provides one of the best, and most romantic, nighttime views in all of Chicago.

  • Signature Lounge - This is one of those things you'll regret if you don't do while visiting Chicago on Valentine's Day, the Signature Lounge providing you with one of the most romantic views in the entire city. Okay, yeah, I know we just said that about the Ferris Wheel, but you'll soon learn that Chicago is full of truly unbeatable views, so it's really hard to choose where the best, most romantic view is.

    Signature Lounge will give you and your partner one of the best meals you've ever had, a handcrafted Valentine's Dinner Date Menu already prepared, and excellent service. The only things you'll need to bring are your snazzy clothes, your date, and maybe your camera!

    Signature Lounge Flickr Group Tours

    Signature Lounge Flickr Group Tours

  • Millennium Park - This is the spot to go for a romantic hand in hand stroll, lovely city skyline views from the ground, and maybe even a little ice skating! Millennium Park is a 24-acre urban park area that holds permanent and temporary art, the outdoor Jay Pritzker Pavilion, and even the all too famous Cloud Gate sculpture (the Bean).Find the perfect spot to grab an iconic couples photo here in the park. Smooching by the Bean seems to be quite popular on Valentine's Day!
    The Bean 2016 Group Tours Staff

    The Bean 2016 Group Tours Staff

  • Art Institute Date - Simple and straightforward, the Art Institute Chicago is one of the absolute finest ar
    Art Institute Chicago Group Tours

    Art Institute Chicago Group Tours

    t museums in all of North America. This being said, of course it is a great date opportunity for those interested in a bit more culture and artistic appreciation. There's nothing quite like roaming the halls of this iconic art museum hand in hand with your other half!

  • Horse-Drawn Carriage - Chicago Carriage provides our favorite choice for true Valentine's Day fun, an authentic Horse-Drawn Carriage ride through the Magnificent Mile! This is just about as romantic as you can get, especially if the scenery and city backdrop are blanketed in snow. Be sure to bundle up and grab a blanket or some cocoa to stay warm during the chilly ride, or maybe just forget we said that and use it as an excuse to snuggle closer to the one you love! 

Check out our great Valentine's Day in Hawaii Blog too!

xoxoGroupTours