CHICAGO: WILDE STYLE

My official date guide for 2025.

Tried and true to my heart, let's enjoy Chicago together.

"Chicago is a town, a city, that doesn't ever have to measure itself against any other city.

Other places have to measure themselves against it. It’s big, it’s outgoing, it’s tough, it’s opinionated,

and everybody’s got a story."

—Anthony Bourdain

After a decade of living in Chicago, it's safe to say that I know my way around. Here are my top recommendations for a great date.

DINING

FINE DINING

Oriole | west loop | 2 michelin stars

This tasting menu elevates to an experience beyond your meal. A blend of French and Japanese cuisine, this uniquely elegant restaurant is a James Beard Award favorite for a reason.

Omakase Yume | west loop | 1 Michelin star

A traditional omakase that emphasizes simplicity, refinement, and technique. They make every bite count.

Indienne | river north | 1 michelin star

Elevated Indian in a fine dining setting. A tasting menu is available for both non-vegetarians and vegans.

Kasama | Wicker Park | 1 michelin star

The first Filipino restaurant to get a Michelin star and one of the best damn meals around. You might know it from THE BEAR, but I know it from delicious breakfast sandwiches and an incredible tasting menu.

Esme | Lincoln Park | 1 MICHELIN STAR

A creative culinary experience that gives back: Michelin-starred, with a focus on art and philanthropy.

CARIñO | UPTOWN | 1 MICHELIN STAR

Contemporary Mexican fare with bold flavors and energetic execution.

Jeong | West Town

Complex and authentic Korean flavors in an ultra-modern, upscale setting.

RELAXED DINING

Daisies | Logan Square

Cozy seasonal pasta made from scratch, included in NYT's 2023 50 Best Restaurants in America list.

Lula Cafe | Logan Square

A farm-to-table staple in hip Logan Square. Simply delicious.

Virtue | Hyde Park

Located in historic Hyde Park, this inviting spot has award-winning soul food. Warning: expect a food coma after this one.

Giant | Logan Square

Little plates with big, bold flavors.

MingHin Cuisine | Chinatown

Traditional dim sum

OTHER

ROMANCE

Aire Ancient Baths | West Loop

Unwind together with Roman-inspired baths and couples massages.

CULTURE

Gene Siskel Film Center | The Loop

Named after the late film critic, enjoy an independent or retrospective screening.

Lyric Opera + Joffrey Ballet | The Loop

Incredible live productions, schedule permitted.

The Salt Shed | west town

Multi-stage live music venue in the old Morton's Salt factory.

Bordel | Wicker Park

Like stepping back to 1920s Paris, sip cocktails and enjoy cabaret sets under tasseled chandeliers and in velvet booths

Dorian's | Wicker Park

Hidden behind a record shop, this moody cocktail bar boasts live music and vinyl-only DJ sets playing over Hi-Fi Italian sound.

The Green Mill | Uptown

This legendary jazz bar might not host Al Capone anymore, but we can still get into trouble.

PLAY

Snakes and Lattes | Wicker Park

Coffee and board games, complete with a vault of new games to play together.

Logan Arcade Bar | Logan Square

A night filled with fun, nostalgia, and some friendly competition. The bar is decked out with 80s/90s classics, pinball machines, and modern games.

AVONDALE BOWL | Avondale

Vintage 8-lane bowling alley with craft cocktails.

King Karaoke | Chinatown

Private karaoke suites with full menu/bar. Let's hear those pipes!

Catcade | Lakeview

For the animal lovers! Part arcade, part animal rescue. A purrfectly fun date day.

Chicago Magic Lounge | Andersonville

Things are not what they seem! Enter through a secret laundromat for a night of mischief and magic.