re: Definitive Chicago Thread / Guide

With 12 people, most restaurants will probably require to reach out ahead of time. Do some checking, but I'm thinking it'll be tough to book anything directly on OpenTable, Resy, and Tock. Don't get booted out of the restaurant for being TOO drunk, but few ideas of places that are used to larger groups: Quartino's, Gibsons Steakhouse (second floor private room), Frontier (full animal ordering available and Wicker is chalked with bars), and Topo Gigio (lively patio, walking distance from Gold Coast, and Wells St + Division makes for a great day and night of bar hopping).

Gibson’s is very good, very loud and lively, too.

Updated OP to include a couple places I've been to recently: Fat Peach in Bridgeport (breakfast/bakery) and Zarella in River North (pizza).

For weekend visitors that don't want to venture into the neighborhoods, Zarella is a great option that is walking distance from many hotels. As you could imagine, it gets pretty crowded. We went at open on Sunday to grab a bar seat.

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OP heading to Three Dots and a Dash Thursday during a small window on business travel? Worth burning my only few hours downtown?

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If you're looking for bright, tropical drinks, go for it. Wouldn't say it's a place too many Chicagoans frequent but it is popular.

If you only have a few hours in the immediate downtown area, I'll say a bar stool at Gilt Bar (or trying your luck downstairs at The Library) or Arbella. The latter has a menu of 'traveling' Old Fashioneds from around the world + a versaile list of classic cocktails. Great spot and may not need to be there as early as Gilt Bar, which can crowd up with people waiting for Bavette's.

ETA: If you're planning on taking the Blue Line back to ORD (assuming it's ORD and not MDW), cocktail bar in West Loop might be the play then you can just walk up to Grand station - After, Bisous and Kumiko are the best in West Loop, but Booze Box (under SUSHI DOKKU), Lazy Bird, and The Aviary / The Office are good plays, as well. If work is footing the bill, totally understand if you're planning Lyft/Uber. Just be sure to monitor traffic because there is construction northbound (outbound) on the Kennedy, which has created some already bad congestion issues.

Any thoughts on the Palmer House Hotel by Hilton? Or at least that general area to stay in for a long weekend?

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Just be sure to monitor traffic because there is construction northbound (outbound) on the Kennedy, which has created some already bad congestion issues.

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I was just there for work taking Clients to the Cubs game Monday and the traffic to/from ORD still sucks. Took the blue line in/out and it was way easier.

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All other things (flight times, $, etc) equal - Midway or O’Hare?

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All things equal, MDW for domestic travel. I probably wouldn't include money because that's pretty dependent on carrier / where you're coming from. You'll have more options on Delta or Southwest into MDW, whereas United completely dominates Terminals 1 and 2 at ORD. I live along the Blue Line and fly almost exclusively to LAX, LGA, and SFO on United for work/family, so I never have much reason to be at MDW.