How to Spend Valentine's Day In Chicago

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I’ve called the Windy City home for almost five years now, which means Mon Cheri and I have had many a romantic adventure since moving here. While we are not actually big on Valentine’s Day, we love to have fun-filled dates that are perfectly applicable for this holiday. Whether you’re visiting Chicago this February 14 or you live here like us and are just looking for new ideas, below are some of my favorite spots and activities for a one of a kind, Chicago Valentine’s.

Play Tourist

If you’re planning a Chicago trip this February, you’re probably already doing this! But many of us who’ve lived here for years (or even their whole lives) seem to always forget the great attractions this city has to offer. While I typically stay away from Navy Pier, a turn on the Ferris Wheel is a great activity for the romantic couple looking for a view. There are also several romantic dinner cruises that depart from the Pier, so you can grab a bite to eat and see the city lights!

Get Cultured

Many a date night with Mon Cheri has been spent exploring the Field Museum or the Shedd Aquarium. Visiting your favorite Chicago Museum is a great way to share your time together this Valentine's Day. I personally recommend the Chicago Art Institute as a Valentine’s date spot, as they have exhibits to suit every taste.

Get Active

Museum date not really your speed? That’s okay because Chicago has so many great activities to try in the winter that make for a perfect Valentine’s Date. My personal favorite winter activity is Ice Skating. Both the Maggie Daley Park Skating Ribbon and the Millenium Park Rink offer free admission (you still have to pay for skate rental).

Grab a Romantic Bite To Eat

There are many great restaurants in the Chicago area, so narrowing down a list of ones romantic enough to suit Valentine's Day was tough! Some of my personal favorites for a great date night are

North Pond

An upscale restaurant with an amazing view of Lincoln Park makes for the perfect combo for Valentine’s Day.

Banderas

Located right on Michigan Ave, they have live jazz music every night and a great menu.

Volare

The perfect Italian menu in the heart of Streeterville. I love this restaurant not only for their great food, but also for their service. When my parents last visited, they went above and beyond to accommodate some dietary needs.

Munno

This restaurant is located right on the border of Uptown and Ravenswood, so I hesitated to include it just because it is a bit far out if you don’t live in the area. But their flatbread pizza is sooooo good I just had to throw them in.

Because February 14 is such a popular evening for dining out, I always recommend calling ahead for reservations no matter where you decide. Also, be sure to check their social and websites as many places offer a special menu for Valentines Day.

Treat your sweet tooth

Nothing is more romantic than sharing an indulgent dessert, and Chicago has no short supply of places to grab something sweet.

Firecakes Donuts

Artisan is an understatement when describing these donuts! Trust me, you’ll want to try them all.

Mindy’s Hot Chocolate

I don’t know whose idea it was to stick the most couple-friendly holiday in the middle of winter, but nothing will warm up your heart and body faster than the most decadent hot chocolate the city has to offer.

Molly’s Cupcakes

Cupcakes. Valentines Day. Nuff Said.

Spend the Night

Maybe you’ve traveled in from the suburbs and don’t want to worry about getting home after a romantic day in the city. Maybe you live in the city, but a messy apartment and some noisy roommates don’t sound like the ideal way to cap off your date night. Either way, these Chicago Hotels are some of my favorites for unwinding and relaxing with your sweetheart.

Hotel Lincoln

If you don’t want to stay in the downtown area, this is a great choice and a comfortable stay. Plus their rooftop bar offers drinks with a great view.

Waldorf Astoria

If you’re looking to spend some $ on this romantic holiday, then this luxury stay is a top choice!

Palmer House Hilton

This hotel is full of Chicago history and offers a beautiful spa with a variety of services if getting pampered together sounds like your idea of a romantic day.

Tip: Call ahead to inquire about Valentine’s packages. Many hotels offer champagne to your room and other special treats for a minimal cost.

I’m sure as time goes on, I’ll only have more to add to this list because we love a good date night! Let me know below your favorite Chicago spots for Valentine’s Day.