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Chicago Magic Lounge bar
Photograph: Courtesy Chicago Magic Lounge

The 8 best ideas for date night in Chicago

Spice up date night with fun activities such as bowling, a magic show and luxurious spa treatments.

Jeffy Mai
Written by
Jeffy Mai
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Chicago is full of fun options for couples. Want a fabulous meal? There are a number of romantic restaurants that offer great food and intimate settings suited for helping you bond with your partner. If you’re more interested in getting out there and doing something, you’ll also find lots of unique activities throughout the city. The following list will give you ideas for the perfect date night, combining dinner recommendations with exciting things to do. And you won’t have to travel far from one place to the other as we’ve kept convenience in mind. The best ideas for date night in Chicago include comedy at The Second City, exploring the gardens at Garfield Park Conservatory, friendly games at Avondale Bowl and more, so don't drop the ball on your love life and get to planning. 

RECOMMENDED: Check out our guide to dating in Chicago 

The best ideas for date night in Chicago

Dinner at The Duck Inn followed by a movie at ChiTown Movies
Photograph: Kate Vogel, courtesy Music Box Theatre

1. Dinner at The Duck Inn followed by a movie at ChiTown Movies

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.

Dinner at Hopleaf followed by a magical performance at Chicago Magic Lounge
Photograph: Jaclyn Rivas

2. Dinner at Hopleaf followed by a magical performance at Chicago Magic Lounge

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.

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Walk through the gardens at Garfield Park Conservatory followed by dinner at Heritage Restaurant & Caviar Bar
Photograph: Jaclyn Rivas

3. Walk through the gardens at Garfield Park Conservatory followed by dinner at Heritage Restaurant & Caviar Bar

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.

Dinner at Topo Gigio followed by a comedy show at The Second City
Photograph: Courtesy Second City

4. Dinner at Topo Gigio followed by a comedy show at The Second City

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.

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Drinks and bites at Mother's Ruin followed by bowling at Avondale Bowl
Photograph: Sean Henderson

5. Drinks and bites at Mother's Ruin followed by bowling at Avondale Bowl

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.

Light bites at Momotaro followed by a spa treatment at Aire Ancient Baths
Photograph: Juan Serrano Corbella

6. Light bites at Momotaro followed by a spa treatment at Aire Ancient Baths

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.

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Explore Mexican culture at the National Museum of Mexican Art followed by dinner at 5 Rabanitos
Photograph: Zach Long

7. Explore Mexican culture at the National Museum of Mexican Art followed by dinner at 5 Rabanitos

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.

Drinks at Central Park Bar followed by karaoke at Alice's Lounge
Photograph: Martha Williams

8. Drinks at Central Park Bar followed by karaoke at Alice's Lounge

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.

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