Dating is a year-round sport. And if you’re going to stay in the game, you have to plan unique and romantic date ideas, especially in a city like Chicago.
To inspire you, I’ve crafted a list of unique date ideas that are just as perfect in the heat of summer as they are in the chill of winter.
Whether you’re single and exploring the lively atmosphere of Chicago or in a relationship and craving something creative for a date night, these 13 captivating ideas are tailor-made to elevate your experiences and ignite the romance.
Unique and Romantic Date Ideas To Try in Chicago
1. Eat Dessert, First
Swap out the fancy cocktail for a delightful dessert at one of Chicago’s many sweet shops. It’s the perfect date idea! Indulge in an Instagram-worthy treat from a West Loop cookie shop or savor a seasonal pie slice from an old-school-inspired bakery and soda shop in Humboldt Park.
2. Laugh Out Loud at a Chicago Comedy or Improv Show
Chicago is home to a colossal comedy scene. For a date night in Chicago that is full of laughs, be sure to check out the host of comedy shows throughout the city, where you can enjoy a mix of stand-up and improv performances. With so many options available, you’re guaranteed a night of fun and entertainment. Don’t miss out—explore the latest comedy shows and book your tickets here.
3. Get Competitive at a Bar with Games
Plan a fun and competitive date night at an interactive game bar. From arcade games to ping pong, billiards, and bowling, these date ideas are a casual and simple way to spend time with your significant other. This date idea is also great for group dates or a couples night out. Game on!
4. Arrange a Romantic Picnic in the Park
Nothing says a classic romantic date more than a picnic in the park. Plan a cheap (but romantic) picnic date. There are 570 Chicago Parks to choose from for this warm weather date idea. For a premium picnic spot, try The Lake Front which is beautiful and provides a scenic view of Lake Michigan. You and your date will have plenty of room to spread out your blankets and lounge in semi-seclusion while enjoying a beautiful landscape in the city.
5. Listen to Beautiful Music during a Candlelight Concert
Experience a romantic evening of music, ambiance, and more at a Candlelight Concert. This transformative experience lets you embrace your favorite artists’ music, beautifully re-imagined by classical instruments. Allow the captivating melodies to wash over you in hidden gem venues, bathed only in the warm glow of candlelight. It’s been one of my favorite dates to date!
6. Take a Stroll Down the Chicago Riverwalk
Enjoy a romantic outdoor date night by exploring The Chicago Riverwalk. The Chicago Riverwalk is a 1.25-mile path along the Main Branch of the Chicago River, featuring entertainment, food, drinks, and shopping. If you’re seeking a convenient date option, the Chicago Riverwalk is the perfect choice.
7. Sneak Through the Backdoor to a Speakeasy Lounge
The Prohibition era is over, but the allure of exclusive, undercover bars is far from being a fad. Experience a hot date surrounded by dimly lit lounges, expertly crafted cocktails, and nightly entertainment at one of Chicago’s speakeasy-themed lounges. Speakeasy lounges are all over the city. Find them in the basement of dive bars, behind mural-painted walls, or through the alleys across various neighborhoods in Chicago.
8. Catch a Flick at a Historic Movie Theater
Take your movie date night up a notch by visiting one of Chicago’s historic movie theaters. These charming venues offer a much cozier and more unique experience than typical large megaplex theaters. They often showcase a mix of classic films and newly released features, adding to their appeal.
9. Explore your Inner Botanist at Local Conservatory
Looking for an easy, budget-friendly first date? Explore a local botanical gem such as a Chicago conservatory. These local gems are filled with thousands of plant species across beautiful indoor gardens and expansive outdoor spaces. Many are free and open year-round, making it perfect for any season! Enjoy a refreshing escape into nature, all at no cost.
10. Dance the night away at a nightclub
Spice up your next date night by heating the dance floor. Whether you prefer premier nightclubs or music lounges, there are plenty of places in Chicago for you and your date to showcase your best dance moves. If you’re looking for great nightlife spots in Chicago, I’ve got the perfect list.
11. Race against the Clock at The Escape Game
Race against the clock with this thrilling interactive date idea in Chicago! The Escape Game offers a heart-pounding 60-minute immersive experience that is both challenging and incredibly fun. Whether you’re with your partner or a big group, you’ll tackle unique themes and puzzles that will keep you on the edge of your seat. Don’t miss out – learn more about the rooms and book your experience here.
12. Learn to make a Savory Feast for Two in a Cooking Class
Spice up your average date night with an interactive cooking class in Chicago. Cooking and dancing lessons all in one evening? What more can you ask for on date night? great place for date night and celebrations of all kinds. Learn a few new skills and have a ton of fun while doing it at this unique cooking school in Chicago.
13. Plan a DIY Taco Tour
Plan your own Taco Tour in Pilsen for a filling and creative date night in the popular Lower West Side neighborhood. Experience the walkable neighborhood as you tour dozens of Mexican restaurants determining who has the best tacos in town. I experienced this date night recently and had an amazing time! Take your date to the next level by ranking each restaurant — perhaps your shared love of tacos will indicate your compatibility as a couple. Note: There is no scientific evidence to support this notion, but it’s worth a try!
Why You Should Try A New Date Night Idea
Dating should always be a fun adventure. Trying out new activities and experiences is what keeps things exciting. These 13 unique ideas are perfect for any time of year and can really add some spark to your outings. Whether you kick things off with dessert or enjoy the cozy vibes of a candlelight concert, there are so many creative ways to connect and make amazing memories in Chicago. So next time you’re planning a date, check out these suggestions to mix in some excitement and romance!
