Delta SkyMiles award flights from Chicago Midway (MDW) to Maui (OGG)
In the last 30 days AwardTool saw Delta SkyMiles award space for MDW→OGG in economy, premium economy and first class. Lowest economy: 24,200 miles + $5.60 (economy space on 13 dates). Lowest first class: 86,400 miles + $5.60 (first-class space on 13 dates). Lowest premium economy: 108,400 miles + $5.60 (premium economy space on 5 dates).
Every airport: Chicago to Maui (OGG) award flights.
Prices observed – ; newest observation .
Page regenerated from the Nov 12, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
- Lowest economy
- 24,200 miles + $5.60
- economy space on 13 dates
- Lowest first class
- 86,400 miles + $5.60
- first-class space on 13 dates
- Lowest premium economy
- 108,400 miles + $5.60
- premium economy space on 5 dates
In economy, 24,200 miles + $5.60 with Delta SkyMiles was the lowest of the 2 programs with economy award space on this route; the next was 33,500 miles + $46.37 with Air France/KLM Flying Blue. With Delta SkyMiles, first class started at 86,400 miles + $5.60, about 3.6 times the points of its lowest economy award (24,200 miles + $5.60).
SkyMiles award prices by cabin
The lowest one-way Delta SkyMiles award AwardTool observed on MDW→OGG in each cabin, in miles plus taxes.
| Cabin | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| Economy | 24,200 miles + $5.60 | 1 stop |  DL | 9+ | 13 | See dates | |
| Premium Economy | 108,400 miles + $5.60 | 1 stop | DL | 9+ | 5 | See dates | |
| First | 86,400 miles + $5.60 | 2 stops | DL | 7 | 13 | See dates |
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 SkyMiles award examples
| Departure | Cabin | Points + taxes | Seats | Stops | Observed (UTC) | |
|---|---|---|---|---|---|---|
| Economy | 24,200 miles + $5.60 | 9+ | 1 stop | Check this date | ||
| Economy | 25,500 miles + $5.60 | 5 | 1 stop | Check this date | ||
| Economy | 30,200 miles + $5.60 | 9+ | 1 stop | Check this date | ||
| Premium Economy | 108,400 miles + $5.60 | 9+ | 1 stop | Check this date | ||
| Premium Economy | 111,600 miles + $5.60 | 5 | 1 stop | Check this date | ||
| Premium Economy | 132,800 miles + $5.60 | 7 | 1 stop | Check this date | ||
| First | 150,300 miles + $5.60 | 7 | 2 stops | Check this date | ||
| First | 157,000 miles + $5.60 | 1 | 2 stops | 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 SkyMiles award space showed up
Departure dates in the next 365 days that AwardTool checked for Delta SkyMiles in the last 30 days, how many had award space in each cabin at any price, and the latest departure with space.
| Cabin | Dates with space | Share of dates checked | Latest departure with space |
|---|---|---|---|
| Economy | 13 of 19 | 68% | |
| Premium Economy | 5 of 19 | 26% | |
| First | 13 of 19 | 68% |
How to get SkyMiles
- American Express Membership Rewards: 1:1 · Instant
Check current transfer bonuses. Most transfers can't be reversed.
SkyMiles vs other programs from Chicago Midway (MDW) to Maui (OGG)
Lowest one-way award per program and cabin on this route.
| Program | Economy | Premium Economy | Business | First |
|---|---|---|---|---|
| Air France/KLM Flying Blue | 33,500 pts + $46.37 | — | 102,000 pts + $62.83 | — |
| Delta SkyMiles | 24,200 pts + $5.60Lowest | 108,400 pts + $5.60Lowest | — | 86,400 pts + $5.60Lowest |
Questions about SkyMiles award flights from Chicago Midway (MDW) to Maui (OGG)
How many miles do you need to fly from Chicago Midway (MDW) to Maui (OGG) with Delta SkyMiles?
The lowest one-way Delta SkyMiles awards AwardTool observed in the last 30 days (newest observation Nov 11, 2026): economy 24,200 miles + $5.60, with a typical monthly low of 35,200 miles (taxes vary) over 7 months and award space on 13 departure dates; premium economy 108,400 miles + $5.60, with monthly lows of 108,400 miles in 2 months and 111,600 miles in 1 month (taxes vary), and award space on 5 departure dates; first class 86,400 miles + $5.60, with a typical monthly low of 157,000 miles (taxes vary) over 7 months and award space on 13 departure dates. Monthly lows varied in economy (24,200 to 59,600 miles + taxes vary), premium economy (108,400 to 111,600 miles + taxes vary) and first class (86,400 to 375,700 miles + taxes vary), so the award on your dates may cost more. Search live before transferring points.
What's the lowest SkyMiles award from Chicago Midway (MDW) to Maui (OGG)?
In economy, 24,200 miles + $5.60. Seen Nov 2, 2026, 18:48 UTC for a Dec 30, 2026 departure. Delta SkyMiles showed economy award space on 13 departure dates at any price (newest observation Nov 11, 2026, 11:39 UTC). In first class, 86,400 miles + $5.60. Delta SkyMiles showed first-class award space on 13 departure dates at any price (newest observation Nov 11, 2026, 11:39 UTC). Search live before transferring points.
Can you book nonstop awards from Chicago Midway (MDW) to Maui (OGG) with SkyMiles?
AwardTool hasn't observed nonstop Delta SkyMiles award space on this route in the last 30 days. That doesn't mean nonstop space never appears.
Which credit card points can book SkyMiles awards from Chicago Midway (MDW) to Maui (OGG)?
American Express Membership Rewards (1:1, Instant). Check current transfer bonuses; most transfers can't be reversed.
When does Delta SkyMiles release award seats for Chicago Midway (MDW) to Maui (OGG)?
Delta SkyMiles publishes a booking window of about 331 days (about 11 months) before departure (AwardTool's program data, reviewed Nov 6, 2026). On this route AwardTool saw Delta SkyMiles award space for departures as late as Sep 21, 2027; seats can open earlier or later, and released seats may already be booked. See SkyMiles award release dates.