Moderator: Hyatt; FlyerTalk Evangelist
Join Date: Jun 2015
Location: WAS
Programs: :rolleyes:, DL DM, Mlife Plat, Caesars Diam, Marriott Tit, UA Gold, Hyatt Glob, invol FT beta tester
Posts: 18,933
For quasi-weekend trips, I see < $800 from MDW on Google Flights.
Most of these are Fri-Sun or Sat-Mon:
Aug 25-27, 26-28
Sep 1-3, 3-5 (Labor Day weekend), 22-24
Oct 13-15, 27-29, 28-30
Nov 3-5, 10-12, 23-25, 25-27 (Thanksgiving)
Note, I'm just going by the results calendar, haven't really tried to book these. A few come up as "call travel agent" so you may have to call in to book and/or might be cached inventory etc. so the price may jump at booking. But worth looking into. MDW-DTW-NRT-SIN RT is 21,528 MQMs based on milecalc. Some results may go through ATL for a bit more.
Under $600 Monday May 22-24, Tues 23-25, other $600+s in May