Award flights from Chicago Midway (MDW) to Maui (OGG)

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In the last 30 days AwardTool saw award space on 2 programs for MDW→OGG. Lowest economy: 24,200 miles + $5.60 (Delta SkyMiles). Lowest first class: 86,400 miles + $5.60 (Delta SkyMiles). Lowest premium economy: 108,400 miles + $5.60 (Delta SkyMiles).

In economy, the lowest award seen was 24,200 miles + $5.60 with Delta SkyMiles on Delta Air Lines flights, against 33,500 miles + $46.37 with Air France/KLM Flying Blue, the next-lowest program. 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).

Every airport: Chicago to Maui (OGG) award flights.

Prices observed Oct 13 – Nov 12, 2026; newest observation Nov 11, 2026, 20:59 UTC.

Page regenerated from the Nov 12, 2026 data snapshot (normally daily). Summary last changed Nov 12, 2026. Seats change quickly.

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Compare programs by cabin

The lowest one-way award each program showed in each cabin, sorted by points.

Economy

Program	Points + taxes	Stops	Airlines seen	Seats	Dates seen	Newest observation
Delta SkyMilesLowest observed	24,200 pts + $5.60	1 stop	DL	9+	13	Nov 11, 2026, 11:39 UTC	See dates
Air France/KLM Flying Blue	33,500 pts + $46.37	2 stops	DL	9+	10	Nov 11, 2026, 20:59 UTC	See dates

Premium Economy

Program	Points + taxes	Stops	Airlines seen	Seats	Dates seen	Newest observation
Delta SkyMiles	108,400 pts + $5.60	1 stop	DL	9+	5	Nov 11, 2026, 04:47 UTC	See dates

Not seen in premium economy: Air France/KLM Flying Blue.

Business Class

Program	Points + taxes	Stops	Airlines seen	Seats	Dates seen	Newest observation
Air France/KLM Flying Blue	102,000 pts + $62.83	2 stops	DL	2	1	Nov 10, 2026, 19:07 UTC	See dates

Not seen in business class: Delta SkyMiles.

First Class

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.

Chicago Midway (MDW) to Maui (OGG) at a glance

From: Chicago Midway International, Chicago, Illinois, United States (MDW)
To: Kahului Airport, Maui, Hawaii, United States (OGG)
Programs with award space seen: 2 of 2 programs tracked on this route
Nonstop award space seen: Not seen in the last 30 days
Airlines seen on these awards: Delta Air Lines (DL)
Departures with open awards: Nov 2026 to Sep 2027
Most dates with space: 13 of 19 departure dates checked (Delta SkyMiles, economy)
Latest departure with space: Sep 21, 2027
Observation window: Awards observed in the last 30 days
Distance: 4,187 miles (6,738 km), great-circle
Destination guide: Award flights to Maui (OGG)

Observed award examples

Awards AwardTool observed for departures in the next 60 days (one way, per traveler)
Departure	Cabin	Program	Points + taxes	Seats	Stops	Observed (UTC)
Dec 30, 2026	Economy	Delta SkyMiles	24,200 pts + $5.60	9+	1 stop	Nov 2, 2026, 18:48 UTC	Check this date
Dec 13, 2026	Economy	Air France/KLM Flying Blue	33,500 pts + $52.12	9+	2 stops	Oct 27, 2026, 02:10 UTC	Check this date
Dec 13, 2026	Premium Economy	Delta SkyMiles	108,400 pts + $5.60	9+	1 stop	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.

Best months to fly from Chicago Midway (MDW) to Maui (OGG) on points

Lowest prices among the dates we observed, by departure month. A record, not a forecast.
Month	Economy	Premium Economy	Business	First
Nov 2026	40,400 pts + taxes not reported (1 date)SkyMiles	111,600 pts + $5.60 (1 date)SkyMiles	—	285,500 pts + taxes not reported (1 date)SkyMiles
Dec 2026	24,200 pts + $5.60 (6 dates)SkyMiles	108,400 pts + $5.60 (3 dates)SkyMiles	—	150,300 pts + $5.60 (6 dates)SkyMiles
Jan 2027	35,200 pts + taxes not reported (1 date)SkyMiles	—	—	157,000 pts + $5.60 (1 date)SkyMiles
Feb 2027	33,500 pts + taxes not reported (2 dates)Flying Blue	108,400 pts + taxes not reported (1 date)SkyMiles	—	158,000 pts + taxes not reported (2 dates)SkyMiles
Mar 2027	33,500 pts + taxes not reported (2 dates)Flying Blue	—	—	375,700 pts + taxes not reported (1 date)SkyMiles
Apr 2027	28,700 pts + taxes not reported (1 date)SkyMiles	—	—	93,900 pts + taxes not reported (1 date)SkyMiles
Sep 2027	29,800 pts + taxes not reported (1 date)SkyMiles	—	102,000 pts + $62.83 (1 date)Flying Blue	86,400 pts + $5.60 (1 date)SkyMiles

A month's taxes are those of an award AwardTool recorded at that month's lowest price for a departure that month. “Taxes not reported” means the data has none for that month; the award still has taxes and fees.

Points that transfer to these programs

US card points to program miles or points: ratio and typical transfer time
Program	Amex	Bilt	Capital One	Chase	Citi	Wells Fargo
Air France/KLM Flying Blue	1:1 · Instant	1:1 · Instant	1:1 · Instant	1:1 · Instant	1:1 · Instant	1:1 · Instant
Delta SkyMiles	1:1 · Instant	—	—	—	—	—

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

Search, calendar and alerts from Chicago Midway (MDW) to Maui (OGG)

Route calendar

Every departure date with open award seats on MDW→OGG for Delta SkyMiles and the other programs: a limited window on the free plan and 365 days with Pro.

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Live search

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Panorama

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How many miles you need from Chicago Midway (MDW) to Maui (OGG)

In economy, Delta SkyMiles had the lowest observed award, 24,200 miles + $5.60; see how many miles you need with Delta SkyMiles.
In premium economy, Delta SkyMiles had the lowest observed award, 108,400 miles + $5.60; see how many miles you need with Delta SkyMiles.
In first class, Delta SkyMiles had the lowest observed award, 86,400 miles + $5.60; see how many miles you need with Delta SkyMiles.

Questions about award flights from Chicago Midway (MDW) to Maui (OGG)

How many points does it take to fly from Chicago Midway (MDW) to Maui (OGG)?

The lowest economy award AwardTool has seen was 24,200 miles + $5.60 with Delta SkyMiles. 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). Search live before transferring points.

Which loyalty programs had award space from Chicago Midway (MDW) to Maui (OGG)?

2 programs in the last 30 days: Delta SkyMiles (economy 13 dates, premium economy 5 dates, first class 13 dates); Air France/KLM Flying Blue (economy 10 dates, business class 1 date). Dates count departure dates with an open award.

Can you fly nonstop from Chicago Midway (MDW) to Maui (OGG) on points?

AwardTool hasn't observed nonstop award space on this route in the last 30 days. The awards it saw connected with 1 to 2 stops on itineraries including Delta Air Lines. That doesn't mean nonstop space never appears.

How much are taxes and fees on award flights from Chicago Midway (MDW) to Maui (OGG)?

Taxes and fees on each program's lowest award ranged in economy from $5.60 with SkyMiles (24,200 miles + $5.60) to $46.37 with Flying Blue (33,500 miles + $46.37). Amounts are one way per traveler in USD and can differ on other dates and routings.

Which credit card points can book awards from Chicago Midway (MDW) to Maui (OGG)?

American Express Membership Rewards: Delta SkyMiles (1:1), Air France/KLM Flying Blue (1:1). Bilt Rewards: Air France/KLM Flying Blue (1:1). Capital One Miles: Air France/KLM Flying Blue (1:1). Chase Ultimate Rewards: Air France/KLM Flying Blue (1:1). Citi ThankYou Points: Air France/KLM Flying Blue (1:1). Wells Fargo Rewards: Air France/KLM Flying Blue (1:1). These are US card programs; ratios come from AwardTool's transfer partner list. Check current bonuses first.

What's the best month to fly from Chicago Midway (MDW) to Maui (OGG) on points?

Counting only month prices from programs with award space on 2 or more dates that month, and leaving out unusually low outliers: in economy, the lowest award was for Dec 2026 departures, 24,200 miles + $5.60 with SkyMiles (6 dates); in premium economy, the lowest award was for Dec 2026 departures, 108,400 miles + $5.60 with SkyMiles (3 dates). The month table shows every lowest price, including those. Based on dates we observed, not a forecast.

When do award seats open for flights from Chicago Midway (MDW) to Maui (OGG)?

Booking windows before departure published by the programs with award space here (AwardTool's program data, reviewed Nov 6, 2026): Air France/KLM Flying Blue about 359 days and Delta SkyMiles about 331 days. AwardTool saw award space on this route for departures as late as Sep 21, 2027; seats can open earlier or later, and released seats may already be booked. See award release dates by program.