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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 romantic dates are seemingly endless. You can go for a more traditional fancy Valentine’s dinner and theater or orchestra event, or opt 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 selections 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. Read on for the best Valentine’s Day date ideas!

Adventure Through the Outdoors

Start the day with some good old-fashioned fun to get your heart pumping and make some memories. Chicago has lots of exciting activities that suit different interests. Get some fresh air and enjoy these fun outdoor date ideas in Chicago​:

  • 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.
  • Walking the Lakefront Trail: The wind can be very cold coming off the lake in winter, but that doesn’t stop Chicagoans from running, walking and biking this beautiful trail. Bundle up and enjoy the vast lake on one side and the city architecture and sparkling lights on the other.
  • Cross-country skiing at Morton Arboretum: Just outside the city, the scenic 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.
  • Exploring the Lincoln Park Zoo: If you’re looking for a casual, affordable date idea, why not stop at the Lincoln Park Zoo — one of the few zoos to offer free admission? You can have fun watching the animals and taking in the stunning natural scenery. Supporting the zoo also helps promote conservation efforts, which means extra brownie points from your environmentally conscious partner.

Sit Back and Be Entertained by Chicago’s Best

On Valentine’s Day, Chicago can be pretty chilly. The weather’s perfect for cuddling up with your partner and enjoying a show. The city is full of fun and engaging entertainment options. Enjoy one of these fun date ideas in Chicago​ for a romantic and exciting 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 exciting shows in a classic venue. 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, you have plenty of options. Try the famous Laugh Factory or visit Second City — where many Saturday Night Live cast members 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. There are tons of gorgeous theaters and a vibrant cultural scene.
  • Chicago Auto Show: If you are a car fanatic couple, you’ll love the Chicago Auto Show, which displays fabulous vehicles from around the world, including concept cars and antique and collector vehicles. Get lost in interactive exhibits that’ll take your date to the next level.

Take a Touristy Approach to Valentine’s Day

Even if you live here, there’s nothing wrong with seeing the touristy sights. Grab a coffee and hold hands while you walk through the stunning streets of Chigaco. These spots make for some of the best Valentine’s Day date ideas​ in Chicago:

  • 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.
  • Navy Pier: Another icon of Chicago sightseeing is the People’s Pier, also known as Navy Pier. There’s something for everyone in this lakefront treasure. Enjoy more than 50 acres of indoor and outdoor attractions, restaurants, shops, parks, concert venues and more. If the weather is nice, try the Ferris wheel or carousel, or head indoors to the botanical gardens and shops when it’s cold.
  • 360 CHICAGO Observation Deck: Head over to The Magnificent Mile to catch stunning views of the Chicago skyline and Lake Michigan from the 360 CHICAGO Observation Deck. As you and your date look at the stunning scenery from over 1,030 feet high, you can gather all your excitement for what the rest of the day has to offer.

Dine in or Eat Out

No Valentine’s date would be complete without a romantic dinner. Whether you plan to spend the day ordering in or eating out, Chicago has some of the most delectable meals and sweet treats to end the night. Here are some of the must-try dishes for an unforgettable, genuinely authentic Chicago Valentine’s Day:

  • Tuck into a classic Chicago deep-dish pizza: In the cold, windy weather, nothing tastes better than a gooey, melty, deep-dish pizza fresh out of the oven. Go all out with a famous Chicago classic at Giordano’s that’ll impress your date. This is the place to go for deep-dish pizza and other Italian classics. Dine in or pick up your pizza to go!
  • Stuff your faces with meatball subs: Is your date the type who’s not afraid to get messy? Then you’ve got to try the deliciously messy meatball sub, one of Chicago’s favorite sandwiches. It also gives you a chance to pull the wipe-their-face-with-a-napkin move — did somebody say Hallmark movie?
  • Have your “Lady and the Tramp” moment with meatballs and spaghetti: Nothing says romance more than sharing a bite of spaghetti and meatballs with your lover. Look for housemade marinara sauce for an authentic and unforgettable experience.
  • Celebrate love with a glass of wine: Sipping wine after a day out in Chicago’s beautiful scenery is a treat your date will cherish. Make it extra special by expertly pairing your pizza and wine according to your date’s tastes. Do they like pineapple on pizza? Rosé will be a perfect match for the sweet and savory flavors. Are they a meat lover? Pair their pizza with a sweet red wine that’ll hit the spot.

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. 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!

Come dine with us on Valentine’s Day — before or after exploring the city and all it offers. Or grab a pizza to go on your way back home or to your hotel — we deliver, too!