Chef John and Karen Shields$295Book 30 days ahead
Smyth in Chicago is the two-Michelin-star West Loop tasting menu from John and Karen Shields, paired with The Loyalist downstairs and produce from their own farm.
Tip: Ask for the wine-pairing 'reserve' option if you have a long evening; the cellar lists a deep run of Burgundy.
Chef Noah Sandoval$295Book 30 days ahead
Oriole in Chicago is Noah Sandoval's two-Michelin-star tasting menu room at 661 W Walnut Street, a 28-seat West Loop room with strong caviar service.
Tip: The wine pairings lean Germanic and Austrian. Ask by region, not by tier; the value is on the long-pour bottles.
Ever 2 ★ ★ 4.7
Chef Curtis Duffy$295Book 30 days ahead
Ever in Chicago is Curtis Duffy's two-Michelin-star Fulton Market tasting menu, opened in 2020 after he left Grace, with rigorous service and quiet plating.
Tip: Sit at the chef's counter if it is offered at booking; the view of the pass is the room's best seat.
Chef Tim Flores and Genie Kwon$245Book 60 days ahead
Kasama in Chicago is Tim Flores and Genie Kwon's Michelin-starred Filipino tasting menu at 1001 N Winchester in Ukrainian Village, doubling as a daytime bakery.
Tip: Day-room bakery and evening tasting menu run separate book-and-pay flows. Plan to come for both, on different days.
Chef Rick Bayless$135 (à la carte)Book 60 days ahead
Topolobampo in Chicago is Rick Bayless's Michelin-starred Mexican fine-dining room at 445 N Clark Street, with menus that rotate every six weeks by region.
Tip: Friday slots open 60 days out and disappear inside an hour. Set a 09:00 alarm for the exact 60-day mark.
Boka 1 ★ ★ 4.5
Chef Lee Wolen$135-185Book 21 days ahead
Boka in Chicago is Lee Wolen's Michelin-starred dining room beside Alinea on Halsted, with a quiet garden courtyard and a brined whole-roast chicken for two.
Tip: Book the garden room in summer. It is one of the prettiest outdoor dining rooms in the city.