Delta SkyMiles award flights from Orlando (MCO) to Chicago Midway (MDW)
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In the last 30 days AwardTool saw Delta SkyMiles award space for MCO→MDW in economy and first class. Lowest economy: 10,600 miles + $5.60 (economy space on 42 dates). Lowest first class: 32,400 miles + $5.60 (first-class space on 42 dates).
Prices observed – ; newest observation .
Page regenerated from the Oct 19, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
- Lowest economy
- 10,600 miles + $5.60
- economy space on 42 dates
- Lowest first class
- 32,400 miles + $5.60
- first-class space on 42 dates
SkyMiles award prices by cabin
The lowest one-way Delta SkyMiles award AwardTool observed on MCO→MDW in each cabin, in miles plus taxes.
| Cabin | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| Economy | 10,600 miles + $5.60 | 1 stop | Delta Air Lines (DL) | 9+ | 42 | See dates | |
| First | 32,400 miles + $5.60 | 1 stop | Delta Air Lines (DL) | 2 | 42 | 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 | 10,600 miles + $5.60 | 9+ | 1 stop | Check this date | ||
| Economy | 14,600 miles + $5.60 | 9+ | 1 stop | Check this date | ||
| Economy | 15,100 miles + $5.60 | 2 | 1 stop | Check this date | ||
| First | 32,400 miles + $5.60 | 2 | 1 stop | Check this date | ||
| First | 36,000 miles + $5.60 | 3 | 1 stop | Check this date | ||
| First | 37,000 miles + $5.60 | 7 | 1 stop | 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 | 42 of 42 | 100% | |
| First | 42 of 42 | 100% |
Best months to fly from Orlando (MCO) to Chicago Midway (MDW) with SkyMiles
| Month | Economy | First |
|---|---|---|
| 16,900 (9 dates) | 38,700 (9 dates) | |
| 10,600 (15 dates) | 32,400 (15 dates) | |
| 15,100 (11 dates) | 36,000 (11 dates) | |
| 14,600 (5 dates) | 36,500 (5 dates) | |
| 19,900 (1 date) | 41,700 (1 date) | |
| 36,600 (1 date) | 53,800 (1 date) |
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 Orlando (MCO) to Chicago Midway (MDW)
Lowest one-way award per program and cabin on this route.
| Program | Economy | Business | First |
|---|---|---|---|
| Air France/KLM Flying Blue | 13,000 pts + $29.09 | 35,000 pts + $44.92 | — |
| American Airlines AAdvantage | 8,000 pts + $5.60Lowest | — | 18,000 pts + $5.60Lowest |
| Delta SkyMiles | 10,600 pts + $5.60 | — | 32,400 pts + $5.60 |
| Qantas Frequent Flyer | 13,800 pts + $5.60 | 29,000 pts + $5.60Lowest | — |
| United MileagePlus | 15,000 pts + $5.60 | — | 44,200 pts + $5.60 |
| Virgin Atlantic Flying Club | 18,500 pts + $5.60 | — | 62,500 pts + $11.20 |
Questions about SkyMiles award flights from Orlando (MCO) to Chicago Midway (MDW)
How many miles do you need to fly from Orlando (MCO) to Chicago Midway (MDW) with Delta SkyMiles?
The lowest one-way Delta SkyMiles awards AwardTool observed in the last 30 days (newest observation Oct 19, 2026): economy 10,600 miles + $5.60, with a typical monthly low of 15,100 miles over 6 months and award space on 42 departure dates; first class 32,400 miles + $5.60, with a typical monthly low of 36,500 miles over 6 months and award space on 42 departure dates. Monthly lows varied in economy (10,600 to 36,600 miles) and first class (32,400 to 53,800 miles), so the award on your dates may cost more. Search live before transferring points.
What's the lowest SkyMiles award from Orlando (MCO) to Chicago Midway (MDW)?
In economy, 10,600 miles + $5.60. Seen Oct 19, 2026, 15:35 UTC for a Nov 10, 2026 departure. Delta SkyMiles showed economy award space on 42 departure dates at any price (newest observation Oct 19, 2026, 15:35 UTC). In first class, 32,400 miles + $5.60. Seen Oct 19, 2026, 15:35 UTC for a Nov 10, 2026 departure. Delta SkyMiles showed first-class award space on 42 departure dates at any price (newest observation Oct 19, 2026, 15:35 UTC). Search live before transferring points.
Can you book nonstop awards from Orlando (MCO) to Chicago Midway (MDW) 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 Orlando (MCO) to Chicago Midway (MDW)?
American Express Membership Rewards (1:1, Instant). Check current transfer bonuses; most transfers can't be reversed.
Which months had the lowest SkyMiles award prices from Orlando (MCO) to Chicago Midway (MDW)?
Counting only month prices from programs with award space on 2 or more dates that month, and leaving out unusually low outliers, the lowest economy award AwardTool observed was for Nov 2026 departures: 10,600 miles (15 dates). The month table shows every lowest price, including those. Based on dates we observed, not a forecast.