Best Valentine’s Date Night Ideas in Chicago

If you’re looking for fun and interesting Valentine’s Day ideas in Chicago, you’ve come to the right place. This bustling city has something for everyone, and on Valentine’s Day, the options for fun and romantic dates are seemingly endless. You can go for a more traditional fancy Valentine’s dinner out and a theater or orchestra event, or go for a more casual and quirky date night with ice skating and pizza.

For any of these options, and everything in between, you’ll find great options in Chicago. Whether you live in the Windy City or are planning a weekend getaway here, Valentine’s Day in Chicago can be loads of fun and will provide excitement for all. Check out all of these top ideas to get your planning started.

Dining Experiences

No Valentine’s date would be complete without dinner. There are so many date night restaurants in Chicago to try, no matter what type of cuisine you’re craving. And whether you want to dine out or carry out your food and eat at home, you’ll find plenty of great places here:

  • Geja’s Cafe: Fondue is a Valentine’s Day classic, and at Geja’s Cafe, you can find this and more, all in a romantic atmosphere. Come here to share a pot of warm fondue and a bottle of wine with your sweetheart by the outdoor fireplace.
  • Virtue: This cozy Hyde Park spot features Southern American cooking and a special Valentine’s Day menu that includes champagne. Dine in at Virtue or choose between carry out or delivery options. Special vegetarian menu options are also available.
  • Le Sud: For French and Mediterranean fare, try Le Sud. The food is amazing and you can enjoy the four-season patio in a heated glamping-like dome.
  • The Bristol: At The Bristol, you and your love can dine on upscale American cuisine from inside their new “snowglobes,” or climate-controlled private tents, for romantic outdoor dining in comfort.
  • Giordano’s: Go all out with a famous Chicago classic at Giordano’s. Consistently landing on the best pizza lists in Chicago, this is the place to go for deep-dish pizza and other Italian classics. Dine in or pick up your pizza to go!

Sight Seeing and Touristy Ideas

Sight Seeing and Touristy Ideas

Chicago has no shortage of touristy things to see, whether you’re new to the area or are a Chicago native, these spots make for some of the best things to do in Chicago for Valentine’s Day:

  • Millennium Park: Full of iconic Chicago sites like Cloud Gate, Crown Fountain, the Pritzker Pavilion, Lurie Garden and more, a walk through Millennium Park is a great way to spend your Valentine’s Day while seeing the sights.
  • Art Institute of Chicago: If you and your sweetheart appreciate fine art, the Art Institute of Chicago is the place to be. This world-class art museum boasts a collection that spans thousands of years and a wide variety of media. Wander the exhibit halls and take in all of the famous artwork here.
  • Willis Tower Skydeck: Formerly known as the Sears Tower, the Willis Tower offers some of the best views of the city. Take a ride up to the top floor where the Skydeck allows for a glimpse of four states and all of the impressive architecture of Chicago, as well as other fun experiences to explore.
  • Navy Pier: Another icon of Chicago sightseeing is Navy Pier. There’s something for everyone here, with more than 50 acres of both indoor and outdoor attractions, restaurants, shops, parks, concert venues and more. If the weather is nice, try the ferris wheel or carousel outside in the park, or head indoors when it’s cold to the botanical gardens and shops.

Outdoor Ideas

On Valentine’s Day, Chicago can be quite chilly, but there are still plenty of ways to have fun outdoors. Get some fresh air and enjoy these fun outdoor Chicago date night ideas:

  • Ice skating at Maggie Daley Park: At Maggie Daley Park, you and your date can skate around the ice ribbon while enjoying the city skyline views. Skate rentals are available, and reservations are required.
  • Walk the Lakefront Trail: The wind can be very cold coming off of the lake in winter, but that doesn’t stop Chicagoans from running, walking, and biking this beautiful trail. Bundle up and enjoy the wide expanse of lake on one side, and the city architecture and sparkling lights on the other.
  • Cross-country skiing at Morton Arboretum: Just outside of the city, the Morton Arboretum spans more than 1,700 acres of woodland and green spaces, with much to explore. Bring your own equipment, or rent skis or snowshoes and explore the miles of trails here. It’s a beautiful way to get some exercise together and have fun outdoors.

Entertainment Ideas

Chicago is full of fun and interesting entertainment ideas too. Pair one of these great outings with a dinner out and you’ve got a romantic Valentine’s night out on the town:

  • Concerts: Check the calendars for available performances on Valentine’s night around town. Try the famous House of Blues for a variety of shows in a classic venue. And whether you like symphony orchestra or hard rock, with so many other venues to choose from, you’re bound to find something to fit your musical tastes.
  • Comedy shows: If comedy is more your speed, there are plenty of options for you too. Try the Laugh Factory or Second City — where many Saturday Night Live alums got their start — or any one of the many other comedy venues in the city.
  • Theater: A night at the theater is one of the best things to do as a couple in Chicago. From ballet and opera to Shakespeare and Broadway, you’ll find all this and more in Chicago, with many gorgeous theaters and a vibrant cultural scene.

Choose Giordano's For Your Next Date Night In Chicago

Choose Giordano’s for Your Next Date Night in Chicago

If your idea of romantic things to do on Valentine’s Day includes sharing a deep-dish Chicago-style pizza with your sweetheart, Giordano’s is the place to be. With hundreds of critics and both local and national headlines declaring Giordano’s the “best pizza” in Chicago, you know you’ll get delicious pizza and quality service when you dine with us.

We are proud to serve Chicago and have many locations throughout the area to choose from. Come dine with us on Valentine’s Day — either before or after exploring the city and all it has to offer. Or grab a pizza to go on your way back home or to your hotel — we deliver too! Once you’ve decided on your Valentine’s Day plans, the only other decision you need to make is what toppings to put on your pizza!