The best date night ideas in Chicago

In search of a really bougie date idea? Look no further than dinner at modern Japanese concept Momotaro followed by soaks at Aire Ancient Baths. You’ll definitely want to keep things on the lighter side before the spa so stick to the indelible pieces of nigiri or the maki rolls. Although Aire is more than a few blocks away from the restaurant, it’s still close enough to quickly get to (and gives you time to digest). Located inside a restored 20,000-square-foot factory, the luxurious bath house offers six thermal pools of varying temperatures, steam rooms and other amenities including couples massages and wine baths. Yes, you’ll spend a pretty penny but you and your date will feel like a million bucks by the time it’s over.

Hidden in Jackson Park, this secret Japanese garden is the perfect place to feel like you and your date are transported out of the city. Chill out amongst the tranquil waterfall, outdoor dojo and beautiful view of the Museum of Science and Industry across the park lagoon. If you happen to visit during the spring, you may be fortunate enough to see the blooming cherry blossoms around the park. Take a short drive over to Hyde Park’s 53rd Street for dinner at Virtue, the award-winning Southern-soul food concept that’s become a neighborhood favorite. Relish in the diverse flavors of dinner, but an essential part of the meal requires diving into the “sweet rations” for unforgettable desserts like the house peach cobbler and banana pudding. 

For an evening of chill vibes and casual games, a quarter-mile stretch on Milwaukee Avenue in Avondale has everything you need. Kick things off at Mother’s Ruin, a casual cocktail bar that originated in New York City. A spiked slushy—the flavors rotate—or craft libation should leave you feeling good (and are all reasonably priced at $12). You’ll definitely want to line the stomach with some bites too; we recommend the pimento cheese plate or the crispy fried chicken sandwich. Then abide The Dude by making your way over to retro-themed Avondale Bowl for friendly competition and White Russians. There are only eight lanes so you’ll probably want to reserve one in advance.

We all hope for a magical ending to a date. The path to getting there starts with dinner and drinks at Hopleaf, an exceptional beer bar on the border of Andersonville and Uptown. Order Belgian-style mussels and frites to munch on and wash them down with a craft brew. The massive selection boasts dozens of bottles and drafts so there’s a pour for every palate. When you’re satiated, saunter over to Chicago Magic Lounge. You’ll enter through a faux laundromat before sitting down to spellbinding performances from some of the best magicians in the business. It’s a fun and memorable experience that promises to have you both oohing and aahing.

Move and groove to dance classes of all levels at the Dance Academy of Salsa in Bucktown. The Academy offers lessons for a range of Latin dance styles including salsa, bachata and cha-cha. Drop-in beginners classes happen every week, only cost $25 per person and no experience is required to participate.  After rhythmically working up a sweat, shimmy a few blocks over to Chef’s Special to recuperate some of your energy. The modern takes on classic American-Chinese cuisine, like crab rangoon and dry chili chicken, is sure to give you a proper refuel. With such an active outing, be sure to indulge in the in-house cloud souffle cake for dessert.

The Garfield Park Conservatory is one of Chicago’s most stunning sights and best of all, it doesn’t cost a cent (but donations are appreciated). Bring your date here to marvel at “landscape art under glass,” which features thousands of plants from around the world spread across eight indoor display gardens. During summertime, wander through the 12-acre outdoor gardens to escape the urban bustle of the city. Reservations are required and can be made online. You’re bound to work up an appetite exploring and while the nearby dining options are limited, Heritage Restaurant & Caviar Bar is just a short drive away. Use the money you saved from the free activity and splurge on caviar and bubbles. It’s guaranteed to please.

For a world-class museum experience during date night, look no further than the Art Institute of Chicago. Keep an eye out for free museum days to save money on admission, but revel in the opportunity to traverse classical and contemporary art exhibits at one of Chicago’s best museums. Right across Michigan Avenue, head over to Cindy’s Rooftop for some of the best views of Millenium Park and even better sips on the cocktail menu. The drinks will be sure to sweeten up the night—the brandy-based Grandma’s Candy might make you pucker with spiced pear and manzanilla sherry flavors. If you want to impress, splurge on the exquisite dinner options, including a saffron lamb ragu pasta or a tomahawk ribeye for two.

Nothing lightens the mood more than a good laugh. And few do it better than Chicago’s world-famous comedy club Second City. You’ll want a full belly first so begin the festivities at Topo Gigio, a classic neighborhood trattoria that’s been around for over three decades. Tuscan-style dishes are the specialty here, and the alluring patio is a popular destination on warm nights. Afterwards, visit Second City for one of the various shows performed each night. There are a number of options to suit your sense of humor—just make sure you and your date are on the same page.

For ceramic-enthusiasts looking for ways to start on their first homemade mugs, Chicago Ceramics Center’s “Clay for a Day” sessions are perfect for date night. These one-time sessions are open to all every first and third Friday of the month, with the opportunity to make up to three hand-crafted vessels to bring home. Afterwards, explore the rest of Bridgeport on your way over to Franco’s Ristorante for some authentic Italian-American eats. The family-owned-and-operated business’ extensive pasta menu will appeal to all palates.

Immerse yourself in one of the largest collections of Mexican art in the country at this Pilsen museum. You’ll find more than 18,000 pieces of work, spanning 3,600 years, to take in, as well as rotating exhibits and performances. Bonus: Admission is free. Refuel after the cultural showcase by stopping into 5 Rabanitos for a host of Mexican delights. Chef Alfonso Sotelo whips up traditional and comforting dishes that range from hearty caldo de res to corn tortillas filled with well-seasoned carne asada. Top it off with a round of margs to leave happy and satisfied.

We know getting in front of a crowd and belting out tunes isn’t for everyone, but if it sounds appealing to you and your date, there are many karaoke bars and lounges happy to accommodate. Among our favorites is Alice’s Lounge, a raucous Avondale dive known for its late-night hijinks. Before channeling your inner superstar, gather some liquid courage at Central Park Bar. This cozy watering hole has vintage charm and a spacious patio outfitted with its own bar, picnic tables, porch swings, outdoor games and a firepit. It’s the perfect place to knock back a few beers or shots to get you ready for your big moment in the spotlight.

Dinner and a movie is the quintessential date move that everyone is familiar with. There’s nothing more traditional than enjoying a nice meal and then watching a film together. You can mix things up, though, with something many Chicagoans may not be familiar with: A drive-in theater. First, start your night at The Duck Inn, a retro-inspired gastro-tavern tucked away on a sleepy side street in Pilsen. Owner Kevin Hickey delivers Midwestern fare executed with chef-driven techniques and you can expect options like duck wings, a Chicago-style duck fat hot dog and a whole rotisserie duck. Once you’ve had your fill of fowl, hop in the car and head down the road to ChiTown Movies. This drive-in shows a host of classic movies every evening and you’ll get to view them from the comfort of your vehicle, which is also a boon if you’re on a first date and intend to chat it up.