Violet’s Recommendations

For a seasonal lazy date, let me walk you through the perfect Saturday. Bundle up with your date, as the first destination is ice skating on the Midway. Luckily, on February 14, the Chicago Park District is hosting “Love is in the Air Skate at Midway Plaisance.” There, you can buy your date a rose and split something sweet before capturing the memory with Polaroid photo opportunities set up around the rink. The rink closes for the season on February 17, making Valentine’s Day the perfect excuse to pay one last visit.

After you’re exhausted from skating, falling down (hopefully not pulling your date down with you), and skating some more, lace up your shoes and head to Plein Air Cafe. Plein Air has some of the best hot drinks, along with great food. Since skating was free, I recommend splurging on a chai and hot chocolate and sharing the chorizo burrito and the Plein pancakes. While people watching, you’ll likely witness someone else’s date failing in real time, food arriving to the most hungover person you’ve ever seen, and a surplus of coffee chats.

Lastly, head to Seminary Co-op to support an independent bookstore and enjoy the incredible ambience of the store’s ample seating. You and your date can pick out books for each other, sit down with your hot drinks, and dive into your next favorite read.

Shawn’s Recommendations

Flip the classic script on dinner and a movie: watch first, eat second. Nothing builds conversation quite like dissecting a film over shared plates. For a date for a cinephile (or for someone who is desperately pretending to be one), Music Box Theatre delivers. This Lakeview landmark has championed indie and foreign cinema since 1929, complete with a working Wurlitzer organ and atmospheric architecture that feels lifted from another era. Though the velvet curtains and retro decor carry the atmosphere, that’s not all this Lakeview gem has to offer. Show up early for the space’s lounge and garden, a tucked-away space pouring inventive cocktails alongside a surprisingly deep board game library.

After the credits, head south along Southport Avenue for a few minutes before the real test at Tango Sur. This Argentine steakhouse doesn’t take reservations, which means you’ll probably need to wait. Use the time strategically. Parse out what you just watched. Gauge whether they caught that visual callback in the third act, or if you yourself missed it. Discover if they’re the type to have strong opinions about ambiguous endings. The tight route keeps you and your date contained, locked in on the itinerary and on each other. Just film, food, and the eternal question of “Shall we do this again sometime?”

Noël’s Recommendations

For a sweet taste of Chicago’s best, sample its secret clubs and signature music, all in one evening. Start your date at the Chicago Athletic Association, a Gothic-style marvel that gives our campus a run for its money. Built in 1893, the club reserved its billiard tables, bars and amenities for the elite upper class for most of its history, only recently opening its doors to the public. The building retains its insider feel even now, so that walking through its wooden niches feels like being in on a city secret. Dinner can be found in the Drawing Room, which serves cozy American fare (be sure to make a reservation beforehand), while the more competitive among us can head to the Game Room for pool, bocce ball, chess, and drinks.

Next, hit the jazz clubs. Chicago’s homegrown genre can be heard at several locations downtown, but Winter’s Jazz Club presents reliable quality and style Wednesday through Sunday. In the spring and summer, it can be reached by a stroll through Millennium Park and across the river, though winter winds might call for a vehicle. Once inside (tickets should be purchased beforehand), choose your seating carefully: the right side of the venue will immerse you and your date in the drummer’s snares and crashes, while the left side will be awash with piano and guitar. You and your date can wind down with some jazzy licks and arpeggios before heading home.

Emily’s Recommendations

For readers who are picky yet indecisive, here is a specific, modifiable itinerary. Begin by taking the Green Line to Ashland. Here, you’ll find a trio of art galleries clustered around West Town’s overgrown railroad tracks: Bodenrader, Volume, and Secrist Beach, each with shows running through February. Their websites are characteristically vague, but the mystery of wandering empty streets stumbling into strange, occasionally beautiful objects is half the thrill. Once you’ve had your fill, take a coffee break at Chicago roastery Metric’s hole-in-the-wall storefront. Baristas turn their direct-source beans into fantastical seasonal specials—winter features a maize mocha, juniper cappuccino, and black sesame matcha.

Get back on the Green Line at Damen and ride it to Kedzie for the final stop of the date: Garfield Park Conservatory. The Conservatory is an oft booked wedding venue, but, subtext aside, it’s a resplendent, sprawling, scientifically glorious greenhouse attached to a park worthy of the same descriptors. Its pièce de résistance is the Fern Room, a recreation of ancient Illinois covered in ferns and cycads. Winding paths and graffitied benches make for easy strolling and surreptitious canoodling. “The impression of a fairyland,” reads a plaque affixed below a moss-speckled sculpture of a lovers’ embrace.

Alkis’s Recommendations

What could be more romantic than a night of delicious food, breathtaking music, and strolls through some of Chicago’s most beautiful spots?

You’ll begin your evening with an early dinner near the Chicago River (Pizzeria Portofino is a great choice). Afterward, take a leisurely walk along the Riverwalk, which offers a unique sense of calm amid the city’s constant intensity. From there, make your way down North Michigan Avenue, perhaps cutting through Millennium Park to take a selfie at the Bean or admire the other couples ice skating. Finally, arrive at Symphony Center, home of the Chicago Symphony Orchestra (CSO), where the evening’s centerpiece awaits.

On February 14, the CSO will perform a thrilling concert featuring 15-year-old violin prodigy Himari and guest conductor Jaap van Zweden. The program will open with a contemporary piece—Joel Thompson’s orchestral work, To See the Sky—before going back in time to some of the staples of the classical repertoire: Bruch’s iconic Violin Concerto No. 1, a prime opportunity for Himari to showcase her extraordinary virtuosity, and Mozart’s Symphony No. 41 (“Jupiter”), which is packed with lyrical and heartwarming melodies that offer the perfect conclusion to your romantic night out.

Elias’s Recommendations

For art lovers or anyone looking for a unique Valentine’s Day date, take the Red Line to Chicago station and wander down to the Museum of Contemporary Art Chicago. Explore thought-provoking exhibitions, including the Yoko Ono retrospective (running through February 22) and a fascinating group show on Chicago’s LGBTQ+ history (running through August 16). Best of all, admission is free with your student ID, making it easy to linger over the art without worrying about cost.

After your museum visit, stroll down to the historic Goodman Theatre, Chicago’s oldest and largest nonprofit theater. Catch a performance of Holiday (playing through March 1) or The Brief Wondrous Life of Oscar Wao (playing through April 5), both showcasing the theater’s tradition of producing world premieres and shows that have gone on to win Broadway acclaim and Tony Awards. Student tickets start as low as $10 online, making a high-quality theater experience affordable. Between provocative art and captivating live performances, this combination offers a culturally rich, memorable Valentine’s outing without breaking the bank.

Nolan’s Recommendations

Keep it local (and perhaps low stakes) with a stroll around the abundance of gallery spaces on campus. For the ambitious, you can attempt a speed run of them all, but it may be just as worthwhile to spend your time seeing only one or two.

In Theaster Gates’s first ever retrospective in Chicago, he has transformed his history at the University into artifacts (such as glass slides from the Department of Art History) that compellingly testify to community, relationships, and the things we value. Theaster Gates: Unto Thee is on display at the Smart Museum of Art through February 22.

In his first U.S. exhibition, Norwegian abstract painter Fredrik Værslev brings with him eight large-scale paintings that work in geometric abstraction and explore the social semantics of the form. You are sure to find aesthetic gems and rich painterly insights. Fredrik Værslev: The Joy of Painting is on display at the Neubauer Collegium through March 27.

Drawing from classic Chinese philosophy, Leah Ke Yi Zheng’s Renaissance Society exhibition combines traditional Chinese materials with conceptual art methodology to offer insight into the changing nature of existence. Change, I Ching (64 Paintings) is on display at the Renaissance Society through April 12.

To mark the centennial anniversary of the museum’s first major archaeological expedition, the Institute for the Study of Ancient Cultures explores the biblically significant and culturally rich city of Megiddo and the story behind its artifacts. Megiddo: A City Unearthed, A Past Imagined is on display at the Institute for the Study of Ancient Cultures through March 15.

Fourth-year Anju Lukose-Scott is the curator behind Horizon Lines: Reimagining Potentiality. This collection, consisting mostly of photographs and sculptures, explores the image of horizon lines in relation to history, politics, and the future. Horizon Lines: Reimagining Potentiality is on display at the Cochrane-Woods Art Center through February 27.