First-class award flights from Chicago Midway (MDW) to Maui (OGG)

The lowest one-way first-class award each program showed on MDW→OGG, sorted by points.

Program	Points + taxes	Stops	Airlines seen	Seats	Dates seen	Newest observation
Delta SkyMiles	86,400 pts + $5.60	2 stops	DL	7	13	Nov 11, 2026, 11:39 UTC	See dates

Not seen in first class: Air France/KLM Flying Blue.

Not seen means AwardTool hasn't observed this cabin on this route in the last 30 days. It doesn't mean the airline has no seats. Dates seen counts departure dates with an open award in that cabin at any price; newest observation is the latest time AwardTool saw one of them. Seats is the count the program reported when we observed it; some programs report at most 9.

Observed first-class award examples

Awards AwardTool observed for departures in the next 60 days (one way, per traveler)

Departure	Program	Points + taxes	Seats	Stops	Observed (UTC)
Dec 30, 2026	Delta SkyMiles	150,300 pts + $5.60	7	2 stops	Nov 2, 2026, 18:48 UTC	Check this date
Jan 9, 2027	Delta SkyMiles	157,000 pts + $5.60	1	2 stops	Oct 27, 2026, 17:45 UTC	Check this date
Dec 13, 2026	Delta SkyMiles	268,200 pts + $5.60	5	2 stops	Oct 15, 2026, 23:24 UTC	Check this date

Prices are one-way per traveler: the program's points or miles plus taxes and carrier fees in USD, as AwardTool observed them in the observation window. Award space changes constantly. A seat we saw may be gone, and space we haven't seen may exist. Always confirm with a live search before transferring points; most transfers can't be reversed.

How often first-class award space showed up

Of the 19 departure dates in the next 365 days that AwardTool checked for Delta SkyMiles in the last 30 days, 13 (68%) showed first-class award space. The latest departure with space was Sep 21, 2027.

First class compared with economy, by program

Each program's lowest one-way first-class and economy awards on MDW→OGG, in its own points or miles, and how many times the economy points the first-class award needed. — in the last column means one of the two is a mixed-cabin award or was not seen on 2 or more dates.

Airlines seen in first class

Airlines that appeared on the award itineraries AwardTool observed, and the programs that showed them.

• Delta Air Lines (DL): Delta SkyMiles

First class on nearby routes

The lowest first-class award AwardTool observed on related routes, as each route's page shows it: the return direction, other airports in the same cities, and more routes from Chicago Midway (MDW) and to Maui (OGG). One way, in the program's points or miles, with that award's taxes when the data has them.

Route	Lowest observed	Program	Dates seen
Chicago O’Hare (ORD) to Maui (OGG)Another Chicago airport	50,000 points + $25.60	Alaska Atmos Rewards	329
Chicago Midway (MDW) to Minneapolis (MSP)Also from MDW	12,600 miles + $5.60Nonstop	Delta SkyMiles	310
Chicago Midway (MDW) to Detroit (DTW)Also from MDW	14,400 miles + $5.60Nonstop	Delta SkyMiles	319
Chicago Midway (MDW) to Atlanta (ATL)Also from MDW	24,400 miles + $5.60Nonstop	Delta SkyMiles	309
Chicago Midway (MDW) to Calgary (YYC)Also from MDW	35,000 miles + $5.60	American Airlines AAdvantage	63
Seattle (SEA) to Maui (OGG)Also to OGG	40,000 points + $5.60	Alaska Atmos Rewards	329
San Francisco (SFO) to Maui (OGG)Also to OGG	35,000 points + $25.60	Alaska Atmos Rewards	326
Tampa (TPA) to Maui (OGG)Also to OGG	50,000 points + $25.60	Alaska Atmos Rewards	324

US card points to program miles or points: ratio and typical transfer time

Program	Amex	Bilt	Capital One	Chase	Citi	Wells Fargo
Delta SkyMiles	1:1 · Instant	—	—	—	—	—

Check current transfer bonuses. Most transfers can't be reversed.