I'll break it into a few categories. Some of these hotels rotate throughout the year with SKYW, RPA etc taking it sometime and different planes getting it throughout the year. Some of these aren't regular overnights anymore but we still fly to them and you're a broken plane away

1) I want to drink micro beers with fellow snobs and see neat downtown structures

FSD- underrated city, the falls are legit
OMA-downtown with tons of shops and exposed brick bars
MLI- craft beer along the Mississippi
DBQ-downtown and eastern Iowa loves Victorian structures
OKC- bricktown down the road, free happy hour at hotel
GJT- nice hotel and mountain town
DRO- hang out at the chalet with ski bums and cowboys
RAP- downtown at the Grand Budapest hotel
FAR- nice hotel, miss walleye sandwiches and bingo at Lucky's though
DAY- drink local brews on Oregon St, nerd out at the museum
BTV- short trip downtown to drink with almost canadian beer snobs
TVC- beer, wine and cherries flow in pure Michigan
TUL- nice downtown hotel
FWA- downtown beer and baseball, underrated
MEM- southern comfort food all over, not Beale St like old days though
SDF- big upgrade from old days, whiskey samplers everywhere
SPI- stay at the tallest building in the city, Abe Lincoln tributes abound
SUX- great hotel, gamble or enjoy the riverfront, your choice
SAF- food and 200 year old adobe structures all over downtown
PBC- personal favorite, awesome street food and spanish conquistador gold churches everywhere

2) Screw craft beer and neat buildings, I want cheap drinks and a bunch of 20 somethings to enjoy them with.

MSN-State Street next to the hotel
MHK-K-State college bars, $20 covers the night
LSE- more bars than residents
GNV-UF bars everywhere
EYW-haven't had it in awhile Duval street memories live on forever
NAS-Cruise ships and Senior Frog's
FPO-same as NAS but a private beach via boat ride
VPS-beach
MIA-not the Sherry but similar fun can be found with a short Uber ride
CVG-long stay next to Germantown, cross the river for baseball



3) All others seem to fall into 3ish star locations next to the airport or malls. The hotel chain changes but the surrounding area stays the same. A lot of DFW overnights fit into this category