Award flights from Chicago Midway (MDW) to Los Cabos (SJD)
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In the last 30 days AwardTool saw award space on 2 programs for MDW→SJD. Lowest economy: 10,000 miles + $62.85 (American Airlines AAdvantage). Lowest business class: 25,000 miles + $62.85 (American Airlines AAdvantage). Lowest first class: 70,400 miles + $62.85 (United MileagePlus).
Prices observed – ; newest observation .
Page regenerated from the Oct 19, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
Chicago Midway (MDW) to Los Cabos (SJD) at a glance
- From
- Chicago Midway International, Chicago, Illinois, United States (MDW)
- To
- Los Cabos International, Los Cabos, Mexico (SJD)
- Programs with award space seen
- 2 of 2 programs tracked on this route
- Nonstop award space seen
- Yes, in economy and business class, via American Airlines AAdvantage and United MileagePlus
- Airlines seen on these awards
- American Airlines (AA), Alaska Airlines (AS), United Airlines (UA)
- Departures with open awards
- Oct 2026 to Dec 2026
- Most dates with space
- 10 of 10 departure dates checked (United MileagePlus, economy)
- Latest departure with space
- Observation window
- Awards observed in the last 30 days
- Destination guide
- Award flights to Los Cabos (SJD)
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 | 10,000 pts + $62.85 | Nonstop | American Airlines (AA), Alaska Airlines (AS) | — | 6 | See dates | |
| United MileagePlus | 20,000 pts + $62.85 | Nonstop | United Airlines (UA) | 9+ | 10 | See dates |
Business Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| American Airlines AAdvantageLowest observed | 25,000 pts + $62.85 | 1 stopNonstop from 125,500 pts | American Airlines (AA) | — | 6 | See dates | |
| United MileagePlus | 70,400 pts + $62.85 | Nonstop | United Airlines (UA) | 2 | 9 | See dates |
First Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| United MileagePlusLowest observed | 70,400 pts + $62.85 | 1 stop | United Airlines (UA) | 2 | 8 | See dates | |
| American Airlines AAdvantage | 78,000 pts + $62.85 | 1 stop | American Airlines (AA), Alaska Airlines (AS) | — | 5 | See dates |
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 | 10,000 pts + $62.85 | — | Nonstop | Check this date | ||
| Business | American Airlines AAdvantage | 25,000 pts + $62.85 | — | 1 stop | Check this date | ||
| Business | United MileagePlus | 70,400 pts + $62.85 | 2 | Nonstop | Check this date | ||
| First | United MileagePlus | 70,400 pts + $62.85 | 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 10,000 miles via American Airlines AAdvantage, which showed nonstop space on 6 dates (2 programs had nonstop space).
- Business class: nonstop from 70,400 miles via United MileagePlus, which showed nonstop space on 6 dates (2 programs had nonstop space).
Points that transfer to these programs
| Program | Amex | Bilt | Capital One | Chase | Citi | Wells Fargo |
|---|---|---|---|---|---|---|
| American Airlines AAdvantage | — | — | — | — | 1:1 · Instant | — |
| United MileagePlus | — | 1:1 · Instant | — | 1:1 · Instant | — | — |
Check current transfer bonuses. Most transfers can't be reversed.
Search, calendar and alerts from Chicago Midway (MDW) to Los Cabos (SJD)
Route calendar
Every departure date with open award seats on MDW→SJD for United MileagePlus and the other programs: a limited window on the free plan and 365 days with Pro.
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Search Chicago Midway (MDW) to Los Cabos (SJD)How many miles you need from Chicago Midway (MDW) to Los Cabos (SJD)
- In economy, American Airlines AAdvantage had the lowest observed award, 10,000 miles + $62.85; see how many miles you need with American Airlines AAdvantage.
- In business class, American Airlines AAdvantage had the lowest observed award, 25,000 miles + $62.85; see how many miles you need with American Airlines AAdvantage.
- In first class, United MileagePlus had the lowest observed award, 70,400 miles + $62.85; see how many miles you need with United MileagePlus.
Questions about award flights from Chicago Midway (MDW) to Los Cabos (SJD)
What's the lowest Chicago Midway (MDW) to Los Cabos (SJD) award price AwardTool has seen?
In economy, 10,000 miles + $62.85 with American Airlines AAdvantage. Seen Oct 4, 2026, 19:36 UTC for a Nov 30, 2026 departure. American Airlines AAdvantage showed economy award space on 6 departure dates at any price (newest observation Oct 19, 2026, 10:53 UTC). In business class, 25,000 miles + $62.85 with American Airlines AAdvantage. Seen Oct 13, 2026, 21:47 UTC for an Oct 19, 2026 departure. American Airlines AAdvantage showed business-class award space on 6 departure dates at any price (newest observation Oct 19, 2026, 10:53 UTC). Search live before transferring points.
Which loyalty programs had award space from Chicago Midway (MDW) to Los Cabos (SJD)?
2 programs in the last 30 days: American Airlines AAdvantage (economy 6 dates, business class 6 dates, first class 5 dates); United MileagePlus (economy 10 dates, business class 9 dates, first class 8 dates). Dates count departure dates with an open award.
Is there nonstop award space from Chicago Midway (MDW) to Los Cabos (SJD)?
Yes. AwardTool observed nonstop award space in economy and business class, bookable via American Airlines AAdvantage and United MileagePlus. The lowest nonstop award in economy was 10,000 miles with American Airlines AAdvantage.
Which credit card points can book awards from Chicago Midway (MDW) to Los Cabos (SJD)?
Bilt Rewards: United MileagePlus (1:1). Chase Ultimate Rewards: United MileagePlus (1:1). Citi ThankYou Points: American Airlines AAdvantage (1:1). Ratios come from AwardTool's transfer partner list; check current bonuses first.