Award flights from Orlando (MCO) to Chicago Midway (MDW)
Search flights from Orlando (MCO) to Chicago Midway (MDW)
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In the last 30 days AwardTool saw award space on 6 programs for MCO→MDW. Lowest economy: 8,000 miles + $5.60 (American Airlines AAdvantage). Lowest business class: 29,000 points + $5.60 (Qantas Frequent Flyer). Lowest first class: 18,000 miles + $5.60 (American Airlines AAdvantage).
Prices observed – ; newest observation .
Page regenerated from the Oct 19, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
Orlando (MCO) to Chicago Midway (MDW) at a glance
- From
- Orlando International, Orlando, Florida, United States (MCO)
- To
- Chicago Midway International, Chicago, Illinois, United States (MDW)
- Programs with award space seen
- 6 of 6 programs tracked on this route
- Nonstop award space seen
- Yes, in economy, business class and first class, via American Airlines AAdvantage, Qantas Frequent Flyer and United MileagePlus
- Airlines seen on these awards
- American Airlines (AA), Alaska Airlines (AS), JetBlue (B6), Delta Air Lines (DL), United Airlines (UA)
- Departures with open awards
- Oct 2026 to Mar 2027
- Most dates with space
- 42 of 42 departure dates checked (Delta SkyMiles, economy)
- Latest departure with space
- Observation window
- Awards observed in the last 30 days
- Destination guide
- Award flights to Chicago Midway (MDW)
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 | |
|---|---|---|---|---|---|---|---|
| American Airlines AAdvantageLowest observed | 8,000 pts + $5.60 | 1 stopNonstop from 9,500 pts | American Airlines (AA), Alaska Airlines (AS) | — | 41 | See dates | |
| Delta SkyMiles | 10,600 pts + $5.60 | 1 stop | Delta Air Lines (DL) | 9+ | 42 | See dates | |
| Air France/KLM Flying Blue | 13,000 pts + $29.09 | 1 stop | Delta Air Lines (DL) | 9+ | 13 | See dates | |
| Qantas Frequent Flyer | 13,800 pts + $5.60 | Nonstop | American Airlines (AA) | 1 | 31 | See dates | |
| United MileagePlus | 15,000 pts + $5.60 | Nonstop | JetBlue (B6), United Airlines (UA) | 9+ | 41 | See dates | |
| Virgin Atlantic Flying Club | 18,500 pts + $5.60 | 1 stop | Delta Air Lines (DL) | 1 | 13 | See dates |
Business Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| Qantas Frequent FlyerLowest observed | 29,000 pts + $5.60 | Nonstop | American Airlines (AA) | 1 | 33 | See dates | |
| Air France/KLM Flying Blue | 35,000 pts + $44.92 | 1 stop | Delta Air Lines (DL) | 3 | 7 | See dates |
Not seen in business class: American Airlines AAdvantage, Delta SkyMiles, United MileagePlus and Virgin Atlantic Flying Club.
First Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| American Airlines AAdvantageLowest observed | 18,000 pts + $5.60 | 1 stopNonstop from 25,500 pts | American Airlines (AA), Alaska Airlines (AS) | — | 41 | See dates | |
| Delta SkyMiles | 32,400 pts + $5.60 | 1 stop | Delta Air Lines (DL) | 2 | 42 | See dates | |
| United MileagePlus | 44,200 pts + $5.60 | Nonstop | JetBlue (B6), United Airlines (UA) | 9+ | 41 | See dates | |
| Virgin Atlantic Flying Club | 62,500 pts + $11.20 | 1 stop | Delta Air Lines (DL) | 2 | 3 | See dates |
Not seen in first class: Air France/KLM Flying Blue and Qantas Frequent Flyer.
Premium economy: not seen in the last 30 days.
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 award examples
| Departure | Cabin | Program | Points + taxes | Seats | Stops | Observed (UTC) | |
|---|---|---|---|---|---|---|---|
| Economy | American Airlines AAdvantage | 8,000 pts + $5.60 | — | 1 stop | Check this date | ||
| Economy | Qantas Frequent Flyer | 13,800 pts + $5.60 | 4 | Nonstop | Check this date | ||
| Business | Qantas Frequent Flyer | 29,000 pts + $5.60 | 4 | Nonstop | Check this date | ||
| Business | Air France/KLM Flying Blue | 35,000 pts + $44.92 | 3 | 1 stop | Check this date | ||
| First | American Airlines AAdvantage | 18,000 pts + $5.60 | — | 1 stop | Check this date | ||
| First | Delta SkyMiles | 32,400 pts + $5.60 | 2 | 1 stop | Check this date | ||
| First | United MileagePlus | 44,200 pts + $5.60 | 9+ | Nonstop | Check this date | ||
| First | Virgin Atlantic Flying Club | 62,500 pts + $11.20 | 2 | 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.
Nonstop award space
- Economy: nonstop from 9,500 miles via American Airlines AAdvantage, which showed nonstop space on 41 dates (3 programs had nonstop space).
- Business class: nonstop from 29,000 points via Qantas Frequent Flyer, which showed nonstop space on 32 dates.
- First class: nonstop from 25,500 miles via American Airlines AAdvantage, which showed nonstop space on 41 dates (2 programs had nonstop space).
Best months to fly from Orlando (MCO) to Chicago Midway (MDW) on points
| Month | Economy | Business | First |
|---|---|---|---|
| 8,500 · AAdvantage (9 dates) | 29,000 · Qantas (8 dates) | 18,000 · AAdvantage (9 dates) | |
| 8,000 · AAdvantage (15 dates) | 29,000 · Qantas (11 dates) | 18,000 · AAdvantage (15 dates) | |
| 8,000 · AAdvantage (10 dates) | 29,000 · Qantas (10 dates) | 18,000 · AAdvantage (10 dates) | |
| 8,000 · AAdvantage (5 dates) | 29,000 · Qantas (2 dates) | 18,000 · AAdvantage (5 dates) | |
| 8,000 · AAdvantage (1 date) | 29,000 · Qantas (1 date) | 18,000 · AAdvantage (1 date) | |
| 8,000 · AAdvantage (1 date) | 29,000 · Qantas (1 date) | 19,000 · AAdvantage (1 date) |
Points that transfer to these programs
| 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 |
| American Airlines AAdvantage | — | — | — | — | 1:1 · Instant | — |
| Delta SkyMiles | 1:1 · Instant | — | — | — | — | — |
| Qantas Frequent Flyer | 1:1 · Instant | — | 1:1 · ~1-2 days | — | 1:1 · Instant | — |
| United MileagePlus | — | 1:1 · Instant | — | 1:1 · Instant | — | — |
| Virgin Atlantic Flying Club | 1:1 · Instant | 1:1 · Instant | 1:1 · Instant | 1:1 · Instant | 1:1 · Instant | 1:1 · Instant |
Check current transfer bonuses. Most transfers can't be reversed.
Search, calendar and alerts from Orlando (MCO) to Chicago Midway (MDW)
Route calendar
Every departure date with open award seats on MCO→MDW for Delta SkyMiles and the other programs: a limited window on the free plan and 365 days with Pro.
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Search Orlando (MCO) to Chicago Midway (MDW)How many miles or points you need from Orlando (MCO) to Chicago Midway (MDW)
- In economy, American Airlines AAdvantage had the lowest observed award, 8,000 miles + $5.60; see how many miles you need with American Airlines AAdvantage.
- In business class, Qantas Frequent Flyer had the lowest observed award, 29,000 points + $5.60; see how many points you need with Qantas Frequent Flyer.
- In first class, American Airlines AAdvantage had the lowest observed award, 18,000 miles + $5.60; see how many miles you need with American Airlines AAdvantage.
Questions about award flights from Orlando (MCO) to Chicago Midway (MDW)
What's the lowest Orlando (MCO) to Chicago Midway (MDW) award price AwardTool has seen?
In economy, 8,000 miles + $5.60 with American Airlines AAdvantage. Seen Oct 19, 2026, 15:35 UTC for a Nov 10, 2026 departure. American Airlines AAdvantage showed economy award space on 41 departure dates at any price (newest observation Oct 19, 2026, 15:35 UTC). In business class, 29,000 points + $5.60 with Qantas Frequent Flyer. Seen Oct 16, 2026, 22:59 UTC for an Oct 23, 2026 departure. Qantas Frequent Flyer showed business-class award space on 33 departure dates at any price (newest observation Oct 19, 2026, 15:35 UTC). Search live before transferring points.
Which loyalty programs had award space from Orlando (MCO) to Chicago Midway (MDW)?
6 programs in the last 30 days: American Airlines AAdvantage (economy 41 dates, first class 41 dates); Delta SkyMiles (economy 42 dates, first class 42 dates); Air France/KLM Flying Blue (economy 13 dates, business class 7 dates); Qantas Frequent Flyer (economy 31 dates, business class 33 dates); United MileagePlus (economy 41 dates, first class 41 dates); Virgin Atlantic Flying Club (economy 13 dates, first class 3 dates). Dates count departure dates with an open award.
Is there nonstop award space from Orlando (MCO) to Chicago Midway (MDW)?
Yes. AwardTool observed nonstop award space in economy, business class and first class, bookable via American Airlines AAdvantage, Qantas Frequent Flyer and United MileagePlus. The lowest nonstop award in economy was 9,500 miles with American Airlines AAdvantage.
Which credit card points can book awards from Orlando (MCO) to Chicago Midway (MDW)?
American Express Membership Rewards: Delta SkyMiles (1:1), Air France/KLM Flying Blue (1:1), Qantas Frequent Flyer (1:1), Virgin Atlantic Flying Club (1:1). Bilt Rewards: Air France/KLM Flying Blue (1:1), United MileagePlus (1:1), Virgin Atlantic Flying Club (1:1). Capital One Miles: Air France/KLM Flying Blue (1:1), Qantas Frequent Flyer (1:1), Virgin Atlantic Flying Club (1:1). Chase Ultimate Rewards: Air France/KLM Flying Blue (1:1), United MileagePlus (1:1), Virgin Atlantic Flying Club (1:1). Citi ThankYou Points: American Airlines AAdvantage (1:1), Air France/KLM Flying Blue (1:1), Qantas Frequent Flyer (1:1), Virgin Atlantic Flying Club (1:1). Wells Fargo Rewards: Air France/KLM Flying Blue (1:1), Virgin Atlantic Flying Club (1:1). Ratios come from AwardTool's transfer partner list; check current bonuses first.
Which months had the lowest 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: in economy, the lowest award was for Nov 2026 departures, 8,000 miles with AAdvantage (15 dates); in business class, the lowest award was for Nov 2026 departures, 29,000 points with Qantas (11 dates). The month table shows every lowest price, including those. Based on dates we observed, not a forecast.