13 Unique and Romantic Date Ideas to try in Chicago

Dating is a year-round sport. Experts share that peak dating starts at the beginning of the year—but who wants to wait that long to go on a unique or romantic date? I don’t. In the spirit of dating and romance, I have created a list of date ideas that are easy to enjoy any time of the year.

If you are single in Chicago or a relationship and just looking for a creative date night with your partner—these 13 unique and romantic date ideas are perfect for you.


Explore your inner botanist at The Garfield Park Conservatory

Garfield Park Conservatory | Image by Taylor Justin

Need an easy first date idea? Explore your inner botanist at the Garfield Park Conservatory with your new love interest. Recognized as one of the coolest hidden gems in Chicago—this date spot houses thousands of plant species from around the world throughout eight indoor display gardens and more than 10 acres of outdoor terraces. Garfield Park Conservatory is free and open to the public every day, making it the perfect place for a date 365 days of the year, especially during the Chicago winter.

Meet up at Chicago’s Original Farmers Market

Need a Sunday date idea? Shop eclectic merchandise while devouring some of the best Mexican food in Chicago at the city’s original “farmers market.” Maxwell Street Market is instrumental to Chicago’s rich history as a city. For about one hundred years, Maxwell Street was one of Chicago’s most unique business and residential districts. While the mile-long street has changed in many instances, what remains are the traditional bargains and international flavor of the Maxwell Street Market. Experience history and more with this casual Sunday date idea.

Laugh Out Loud at a Chicago Improv Show

Image | iO Theater

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 clubs or improv shows in Chicago. Check out at the IO theater located in Chicago’s Lincoln Park Neighborhood; the iO Theater is considered to be the “mecca” of improvisation. The iO theater features four theaters (which shows seven nights a week). See the next comedic star during your next date night in Chicago. To purchase tickets to an improv show at iO Theater, visit iOimprov.com.

Plan a DIY Taco Tour in Pilsen

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. Be sure to add some of my favorites to your lists, such as  El MilargoEl Taco Azteca, and Los Comales. These spots are well known and some of my favorites. Take the date to the next level by ranking each restaurant— hopefully, your shared taste of tacos will forecast your compatibility as a couple. Note, there is no scientific study to prove this study, but it never hurts to try!

Get Competitive at a Bar with Games

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Headquarters Beercade | Image by Taylor Justin

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!

Arrange a Romantic Picnic in The Park

Nothing says 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 Humboldt Park, Douglas Park, or Washington Park. These parks are massive and very scenic. 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.

Sneak through the backdoor to a Speakeasy Lounge

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Bordel | Image by Taylor Justin

The Prohibition-era may be 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 alley across various neighborhoods in Chicago.

Take a Stroll down the Chicago Riverwalk

Spend a romantic summer or fall date night, savoring everything that the Chicago Riverfront has to offer. The Chicago Riverwalk is a 1.25-mile path along the Main Branch of the Chicago River. The Chicago Riverwalk provides several options for a great night out. For entertainment, experience Art on theMart, check out a Chicago Architecture tour or listen to live music at City Winery on the River. Indulge in delicious food and drink options from over a dozen different vendors, representing various neighborhoods and food cultures from around Chicago.

Catch a Flick at a Historic Movie Theater

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Image | Logan Square Theater

Step up your movie date night with a visit to one of Chicago’s infamous movie theaters. These theaters show films from big blockbusters movies to cult classics and more. There are many upsides to watching a movie at one of these theaters. These theaters offer an eclectic taste of films for an admission of $10 or less every single day.

Eat Dessert, First

Trade a fancy cocktail for a creamy dessert at one of my many Chicago’s sweet-shops. Grab an Instagram worthy treat, from a West Loop sweet shop—or a seasonal pie slice from an old school inspired bakery and soda shop in Humboldt Park.

Sample Brews on Malt Row in Ravenswood

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Spiteful Brewing | Image by Taylor Justin

Dubbed “Malt Row” in 2017, the Ravenswood Corridor and surrounding area has quickly earned a reputation as “Chicago most diverse beer destination.” Plan a fun daytime date with your craft-loving comrade a good time as you explore over eight different beer and spirit locations in the North Side neighborhood. For more details about Malt Row, visit the website here.

Dance the Night Away at a Nightclub

Heat up your date night as you set the dance floor on fire on your next date night. From premier nightclubs to music lounges, there are plenty of places for you and your date to show off your best dance moves. If you want a venue that offers not only diverse music but a diverse crowd, check out this list of inclusive nightclub venues in Chicago.

Learn to make a Savory Feast for Two in a Cooking Class

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Image | The Chopping Block

Spice up your average date night with an interactive cooking class at The Chopping Block. Master a new culinary skill at Chicago’s highly acclaimed recreational cooking school with locations in Lincoln Square and River North. From luxurious breakfast recipes to tantalizing Venetian inspired dinners—learn a new skill while making each other a good meal. For the full schedule of available cooking classes, visit the Chopping Block.com

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