Private

The OG garage code

Date Nights

Our guide to eating and drinking well in Chicago. Updated whenever we find somewhere new worth going back to.

Take Her Breath Away

$150–300+ /couple

Ever

West Loop
Contemporary American $285/pp tasting

Two Michelin stars. A progression of 10+ courses that changes completely each visit. One of the best meals in the country.

Reserve on Resy

Oriole

West Loop
New American $295/pp tasting

Hidden in an alley. Two Michelin stars. The kind of dinner where you lose track of how many courses you've had.

Reserve on Tock

Kasama

Ukrainian Village
Filipino ~$185/pp

Two Michelin stars. Filipino tasting menu at night, incredible bakery by day. The longanisa sausage roll is legendary.

Reserve on Tock

Esmé

Lincoln Park
Creative American ~$195/pp

Immersive, theatrical, stunning. Each course tells a story. The room itself is part of the experience.

Reserve on Tock

Indienne

River North
Indian Fine Dining ~$175/pp

Indian cuisine elevated without losing its soul. Spice-forward and refined. A newer addition to Chicago's fine dining scene.

Reserve on Resy

The Perfect Friday

$80–150 /couple

Monteverde

West Loop
Italian / Pasta ~$50-60/pp

Handmade pasta done right. The cacio e pepe tortelloni and tiramisu are non-negotiable.

Reserve on Resy

Rose Mary

West Loop
Croatian-Italian ~$50-70/pp

From the Top Chef winner. The lamb chops and squid ink pasta are the moves. Great cocktail program too.

Reserve on Resy

Ciccio Mio

West Loop
Italian ~$50-70/pp

Cozy, romantic, and the burrata is absurd. Good for a date where you want to linger over wine.

Reserve on Resy

Bavette's Bar & Boeuf

River North
Steakhouse ~$80-120/pp

Dark, sexy, jazz playing. The bone-in ribeye and shrimp de Jonghe are the order. Not your father's steakhouse.

Reserve on OpenTable

Virtue

Hyde Park
Southern American ~$50-70/pp

Warm, soulful, intentional. The fried chicken and catfish are perfect. A neighborhood gem that punches way above.

Reserve on Resy

Mahari

Hyde Park
African Diaspora / Afro-Caribbean ~$50-70/pp

Jean Banchet winner for Best Neighborhood Restaurant 2026. 1504 E. 55th Street, right in the heart of Hyde Park. Hannah's find.

Reserve on SevenRooms

Sepia

West Loop
New American ~$60-90/pp

Elegant without being stuffy. Michelin-starred, seasonal menu, gorgeous cocktails in a beautiful old printing house.

Reserve on OpenTable

Hidden Gems

$40–100 /couple

Tango Sur

Lakeview
Argentinian BYOB ~$35-50/pp

Bring your own wine, get incredible steak. Cash only, no reservations. The skirt steak is the size of your head.

Nadu

Lincoln Park
Regional Indian ~$35-50/pp

Southern Indian flavors you won't find anywhere else in the city. The dosas and curries are deeply spiced and personal.

Reserve on Resy

Mirra

Pilsen
Italian ~$40-55/pp

Neighborhood Italian in Pilsen with real charm. Small menu, everything made with intention.

Lula Cafe

Logan Square
New American ~$40-60/pp

Logan Square institution. Farm-driven, creative, unfussy. The Monday prix fixe is one of the best deals in the city.

Reserve on Resy

Pizz'Amici

West Town
Pizza ~$30-45/pp

Neapolitan pizza that rivals anything in the city. Quick, casual, and genuinely excellent. Good for a low-key night.

Close to Home

Roka Akor

Oak Brook
Japanese ~$70-100/pp

Robata grill, excellent sushi, and cocktails. The closest thing to a proper date night without driving downtown.

Reserve on OpenTable

RH Rooftop

Oak Brook
American ~$50-70/pp

On top of the Restoration Hardware store, which sounds odd but works. Beautiful space, solid brunch and dinner.

Violí

Oakbrook Terrace
Greek ~$55-75/pp

Greek done well, close to home. Good grilled octopus and lamb chops.

Entourage

Nearby
Lounge/Dining

When you want to be out but not too far. Easy, familiar, good energy.

Brunch

Lula Cafe

Logan Square

Weekend brunch is an institution. Get there early or prepare to wait.

Kasama

Ukrainian Village

Daytime cafe, no reservation needed. The pastries and Filipino brunch dishes are outstanding.

Buttercup

South Loop

Bright, welcoming, and the kind of brunch that makes you feel like you have your life together.

Cafe Yaya

Lincoln Park

Mediterranean-inspired, sunny patio when the weather cooperates. The shakshuka is excellent.

After Dinner

Kumiko

West Loop · Japanese cocktails

Lazy Bird

West Loop · Speakeasy in The Hoxton

The Drifter

River North · Hidden speakeasy

Green Mill

Uptown · Legendary jazz

Winter's Jazz Club

South Loop · Intimate jazz

Chicago Magic Lounge

Andersonville · Close-up magic

Bordel

Wicker Park · Hidden flamenco and jazz

Three Dots and a Dash

River North · Tiki bar

Full Evening Plans

The West Loop Classic

Kumiko for cocktails, Monteverde for dinner, Lazy Bird for a nightcap

$180–250

The Showstopper

Ever tasting menu. That's the whole night.

$600–750

The BYOB Budget King

Grab a bottle at a wine shop, Tango Sur for steak, Jeni's Ice Cream to walk it off

$100–140

Culture & Soul Food

Art Institute in the afternoon, Virtue for dinner

$150–220

Mystery & Magic

The Drifter for drinks, Bavette's for steak, Chicago Magic Lounge for the finale

$250–350

The Adventurous Foodies

Browse Wicker Park, Kasama or Crying Tiger for dinner, Bordel for the after-party

$180–280