01
Boeufhaus
A neighborhood steakhouse with serious cooking and none of the downtown ceremony.
- BEST FOR
- A low-key celebration
- THE MOVE
- Share a steak and linger
A LOCAL EATER’S LITTLE BLACK BOOK · UPDATED JULY 2026
Ten reasons
to make a reservation.
The Chicago meals I keep returning to—and the tables I recommend first. Each pick includes the occasion, the move, and the fastest way to plan your visit.
THE WINDY CITY
AT ITS TASTIEST
Not a ranking. A tightly edited guide to ten places that capture why Chicago is one of the world’s great eating cities.
✳THE SHORTLIST
10 personally selected tables
Where to eat now.
FILTER BY MOOD
10 TABLES
02
Topo Gigio Ristorante
Warm, lively Italian dining that feels equally right for a date or a full family table.
- BEST FOR
- An easygoing night out
- THE MOVE
- Pasta, wine, no rushing
03
Armitage Alehouse
A moody, transportive pub where polished hospitality meets deeply comforting food.
- BEST FOR
- A cozy date night
- THE MOVE
- Book early; stay for dessert
04
Bavette’s Bar & Boeuf
Dim lights, impeccable atmosphere, and the kind of steakhouse experience people remember.
- BEST FOR
- A big-deal dinner
- THE MOVE
- Arrive early for the bar
05
Au Cheval
A legendary Chicago burger in a dark, bustling room that turns waiting into part of the ritual.
- BEST FOR
- An indulgent lunch
- THE MOVE
- Go off-peak; expect a wait
06
Asador Bastian
A refined celebration of live-fire cooking in a handsome brownstone setting.
- BEST FOR
- A destination dinner
- THE MOVE
- Let the team guide the order
07
Gibsons Bar & Steakhouse
Big-city energy and old-school Chicago confidence, delivered at full volume.
- BEST FOR
- Out-of-town guests
- THE MOVE
- Embrace the classic experience
08
RPM Seafood
A polished riverfront room for seafood towers, celebratory energy, and skyline views.
- BEST FOR
- A downtown celebration
- THE MOVE
- Ask for a river view
09
Trivoli Tavern
A hidden-away supper club with flattering light, generous plates, and effortless charm.
- BEST FOR
- Dinner before a night out
- THE MOVE
- Start with a martini
10
Sunda New Asian
A lively River North destination for sushi, Southeast Asian flavors, and an energetic night out.
- BEST FOR
- Date night or a group dinner
- THE MOVE
- Share several plates
BEHIND THE LIST
A frequent flyer’s
Chicago constants.
I’m a Chicago local and corporate pilot who has eaten across the country and around the world. These are the places I miss when I’m away—and recommend when someone asks where to eat here.
The list favors memorable hospitality, a strong sense of place, and meals worth repeating. It is personal by design and revisited throughout the year.
— BRETT VELEZ Chicago, July 2026