Good date ideas in Chicago aren’t hard to find. A city so alive with fascinating history, good food, and gorgeous architecture is a spot-on setting for letting love grow. But with so much to do, you might feel overwhelmed.

If you find yourself in Chicago wondering, “Where can I go for a date?”, don’t panic! Whether you’re a well-versed local or an out-of-towner still browsing flights to Chicago, this guide to the good stuff in Windy City will give you Chicago date night ideas for your first, second, or seventieth date.

What are the best first date ideas in Chicago?

Feeling nervous about that first date? No way! Impress the object of your affection and yourself with a memorable meetup—and if things go well, rest assured that these make wonderful second date ideas for Chicago, too.

The Village

It’s the oldest Italian restaurant in Chicago, but that’s only one of its charms. The Village’s interior is painted to resemble a rustic Italian countryside, putting it firmly on the list of cute date ideas in Chicago—but it’s fun and low-key enough for a first date. The restaurant serves lunch and dinner, so you can book a low-pressure daytime date and still make a memorable impression.

Lula Cafe

Who says first dates have to be nighttime affairs? Lula Café is a unique, bohemian space where farm-to-table is the name of the game. It’s open for three meals a day, but you can’t beat their brunch. Your date will appreciate the uncluttered yet intimate interior—perfect for leaning in close and sharing conversation. And you’ll appreciate a late-morning meetup that leaves the whole day ahead for more adventures with your new flame.

What fun date ideas in Chicago don’t require a reservation?

Romance doesn’t always follow a schedule. What is the perfect date that doesn’t require pre-planning? Maybe one of these great last-minute ideas:

Art Institute of Chicago

Chicago is one of the most art-forward cities in America, and the Art Institute is one of Chicago’s greatest cultural contributions. More than just a well-rounded museum, the Art Institute also houses libraries, children’s activities, and a beautiful museum shop. Plus, it’s open seven days a week, making the Art Institute of Chicago ideal for unplanned romantic outings.

Lou Malnati’s Pizzeria

Sure, deep-dish is so popular, it’s practically a Chicago cliché. But that’s because it’s so fantastically scrumptious! And digging into a gooey, saucy pie with the object of your affections is the kind of dynamic date that’s a feast for all the senses. While it’s hard to find a bad deep-dish pizza in Chicago, you can’t go wrong at Lou Malnati’s. And with several locations in Chicago—none of which take reservations—you’ll never feel like you’re running behind. Pro tip: When you arrive, you can pre-order your pizza while waiting for a table.

What are some fun active date ideas in Chicago?

What activities should you do on a date when you want to get to know someone? Sipping wine and strolling the sidewalk are great, but why not get some adrenaline in the mix? Find out what your date is made of—and show them your adventurous side—with unique date ideas in Chicago that are so much more energetic than dinner and drinks:

Maggie Daley Park

If the idea of getting your heart pumping with someone special makes your heart go pitter-patter, head to Maggie Daley Park. You’ll find no shortage of outdoor activities to help you pass some quality time with your date. There are picnic grounds if you want to dine al fresco, a mini golf course for playfully pitting your skills against your attractive opponent, and—for you really wild ones—a rock climbing wall with three different levels of difficulty.

Jet Ski on Lake Michigan

If the weather’s fine and you’re in the mood for a daring date, head to the shore of Lake Michigan and rent a jet ski. You can each rent your own for some friendly competition, or share a ride and hold each other tight as you fly across the waves. Chicago Water Sport Rentals is open both weekdays and weekends, and you can rent jet skis by the half-hour or the hour.

What are the best romantic date ideas in Chicago?

First dates are great fun, and brand-new relationships can be thrilling. But what can couples do in Chicago when they want to create an unforgettably romantic experience together? Try these ideas:

Millennium Park

It’s a garden, an outdoor art exhibition, an event space, and a fabulous photoshoot backdrop all in one. Millennium Park is home to Chicago’s famous Cloud Gate sculpture—also known as The Bean—as well as other art and landscape masterpieces. Not only is it close to some of the best hotels in Chicago, it could easily be the centerpiece of an entire weekend in Chicago. Did we mention that Millennium Park is perfectly situated for stunning photos with your sweetheart, particularly if you’re planning on asking a very important question…?

The Lobby

Defy expectation and take your one-and-only out for a swanky afternoon tea. The Lobby at The Peninsula Hotel is a posh setting for an unexpected (and very romantic) daytime date. Intimate, elegant, and surprising—isn’t that what you want a special occasion to be? Whether you live locally or are in town for a memorable getaway, you might want to book a room —it’s one of the loveliest hotels in the city.

What are the best late-night date ideas in Chicago?

When date night in Chicago turns to late night in Chicago, you might not be in the mood to pop into the nearest dive bar. No worries—there are plenty of great joints perfect for a late date night in the city:

The Gage

The ambience is great, the cocktails are inventive, and the kitchen is open until at least 10 p.m. (and even later on weekends). If you find yourself craving a late-night bite or tasty drink after a movie or a show, bring your sweetie to The Gage. It’s a wonderful setting to share scrumptious flavors and midnight conversations.

The Second City After Hours

The Second City is a famous comedy joint. And once you catch their late-night After Hours show, you’ll agree that its reputation for unparalleled comedy is well deserved. The Second City After Hours is an off-the-wall hour of interactive improv every Friday and Saturday at 11 p.m. Get dinner before the show and drinks afterward, and you’ve got an unforgettable date night.

The Windy City is the perfect place to sweep a special someone off their feet. If you want to continue your whirlwind romance, check out our guide for to how to spend your weekend in Chicago. We’ll see you there.

 

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