State Street Bridge 060415.jpg

The City of Chicago is rife with things to do any day of the year, so you’re in a great spot for the feted February 14th! From horse-drawn carriage rides to shopping on the Magnificent Mile, to games on the Pier to helicopter tours, there is no shortage of inventive Chicago Valentines Day date ideas! Chicago offers plenty of opportunities to impress your significant other with a romantic Windy City getaway. And there’s no shame in taking a romantic romp for two at a luxury downtown Chicago hotel, or taking each other out to eat at one of many fine dining establishments in the area. You’re definitely in the right city for romance this Valentines Day in Chicago; here are a few ideas to make your Windy City Valentine’s Day a memorable one. Whatever you decide to do for Valentines this year, don’t forget the Chicago Valentines Day flowers! Whether it’s roses, daisies, tulips or orchids that tickle her fancy, you won’t come up short on the romance stick when you send Valentines flowers in Chicago!

1. Luxury Hotel Getaway for Two

As an A-list destination city, Chicago offers an abundance of romantic and luxurious hotels for an in-town getaway. Choose from one of the following and ask for the Romance Package, which varies at each but generally includes a dinner or breakfast, wine or champagne and cheese or strawberries, a romantic view and plush accommodations for two: The Drake, The Elysian, Four Seasons, Intercontinental or The Peninsula.

2. Dining a Deux

The Magnificent Mile and surrounding streets in particular hold a host of renowned and tasty restaurants that are perfect for an intimate dinner for two – or even for a double or group date of four or more. Call ahead for the specific restaurant’s special Valentines menu and drink specials. Try to get in at one of these entertaining, famous haunts: Signature Room at the 95th, RPM, The Marq, Naha, or Spiaggia.

3. The Jeweler’s Row

This historic jewelry mall features dealers from all over the world, who will surely have the right something shiny (and measured in carats) for your special someone. Take a stroll hand-in-hand and window shop the blazing baubles or actually partake in a sale for your swooning sweetie!

4. Horse-Drawn Carriage Ride

A horse-drawn carriage ride around the Magnificent Mile is about as romantic as they come. Make sure to bundle up and bring along a blanket to snuggle under with your Valentine. Grab a cup of steaming cocoa or tea as your ride is sure to be brisk in the Windy City’s winter night! Check out for details and pricing.

One Summer Night in the Windy City.jpg

5. Odyssey Dinner Cruise

With Lake Michigan being the foremost sight on this beautiful cruise with panoramic views of Chicago. Take your love on a mini cruise and see the Chicago skyline like never before. In addition, you’ll enjoy fine dining aboard this luxury yacht! What could be better than an elegant dinner, dancing, a yacht ride, expansive views and endless romance?

6. Navy Pier Walk (and Ride)

Walk, run, eat, shop, play… it’s all on the famous Navy Pier in the Windy City of Chicago, Illinois this Valentines Day. For loads of entertainment and endless fun, take a stroll up and down this world-famous attraction and experience it for yourselves! Sure it could be a little chilly, so bundle up! Get ready to play challenging yet fun carnival games with your partner, do some souvenir shopping, wine and dine and snack, and who knows what else! You’ll have a blast perusing the Pier.

7. Helicopter Tour of the City

Take a sky-high trip of the Windy City and see all the sights from miles above! You’ll never forget this one-of-a-kind romantic romp with your lover! Take in Lake Michigan, the Magnificent Mile, Navy Pier and the bright Chicago skyline hand-in-hand from the air! For prices and packages offered, check out