Business-class award flights from Chicago Midway (MDW) to Los Cabos (SJD)
Explore these award routes
Preview matching cached flight results on these routes, then search live for your own trip.
In the last 30 days AwardTool saw business-class award space on 2 programs for MDW→SJD. Lowest: 25,000 miles + $62.85 with American Airlines AAdvantage, which showed business-class award space on 6 dates. Nonstop business-class space was seen via American Airlines AAdvantage and United MileagePlus.
Prices observed – ; newest observation .
Page regenerated from the Oct 19, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
- Lowest observed
- 25,000 miles + $62.85
- American Airlines AAdvantage
- Programs with space
- 2 of 2
- programs seen on this route
- Most dates seen
- 9 of 10
- dates checked · United MileagePlus
- Nonstop
- Seen
- from 70,400 miles + taxes vary
Compare programs for business class
The lowest one-way business-class award each program showed on MDW→SJD, sorted by points.
| 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 |
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 business-class award examples
| Departure | Program | Points + taxes | Seats | Stops | Observed (UTC) | |
|---|---|---|---|---|---|---|
| American Airlines AAdvantage | 25,000 pts + $62.85 | — | 1 stop | Check this date | ||
| United MileagePlus | 70,400 pts + $62.85 | 2 | Nonstop | Check this date | ||
| United MileagePlus | 70,400 pts + $62.85 | 3 | 1 stop | Check this date | ||
| American Airlines AAdvantage | 86,500 pts + $62.85 | — | 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 business-class award space showed up
Departure dates in the next 365 days that AwardTool checked for each program in the last 30 days, how many had business-class award space at any price, and the latest departure with space.
| Program | Dates with space | Share of dates checked | Latest departure with space |
|---|---|---|---|
| American Airlines AAdvantage | 6 of 10 | 60% | |
| United MileagePlus | 9 of 10 | 90% |
Nonstop business-class award space
- American Airlines AAdvantage: nonstop from 125,500 miles; nonstop space on 3 dates.
- United MileagePlus: nonstop from 70,400 miles; nonstop space on 6 dates.
Lowest business class award by month and program
Each program's lowest one-way business-class award by departure month, in its own points or miles; taxes vary. — means the program showed no business-class space that month.
| Program | |||
|---|---|---|---|
| American Airlines AAdvantagemiles | 25,000 | 86,500 | 48,500 |
| United MileagePlusmiles | 70,400 | 72,200 | 101,000 |
Airlines seen in business class
Airlines that appeared on the award itineraries AwardTool observed, and the programs that showed them.
- American Airlines (AA): American Airlines AAdvantage
- United Airlines (UA): United MileagePlus
Business class on nearby routes
The lowest business-class award AwardTool observed on related routes, as each route's page shows it: the return direction, other airports in the same cities, and more routes from Chicago Midway (MDW) and to Los Cabos (SJD). One way, in the program's points or miles; taxes are on each route's page.
| Route | Lowest observed | Program | Dates seen |
|---|---|---|---|
| Chicago O’Hare (ORD) to Los Cabos (SJD)Another Chicago airport | 20,000 milesNonstop | American Airlines AAdvantage | 104 |
| Chicago Midway (MDW) to Shanghai Pudong (PVG)Also from MDW | 372,200 miles | United MileagePlus | 76 |
| Chicago Midway (MDW) to Tokyo Haneda (HND)Also from MDW | 113,500 miles | American Airlines AAdvantage | 61 |
| Chicago Midway (MDW) to Paris Charles de Gaulle (CDG)Also from MDW | 57,500 miles | American Airlines AAdvantage | 28 |
| Chicago Midway (MDW) to Amsterdam (AMS)Also from MDW | 90,000 points | Qantas Frequent Flyer | 8 |
| San Francisco (SFO) to Los Cabos (SJD)Also to SJD | 20,000 miles | American Airlines AAdvantage | 327 |
| Seattle (SEA) to Los Cabos (SJD)Also to SJD | 20,000 miles | American Airlines AAdvantage | 320 |
| Denver (DEN) to Los Cabos (SJD)Also to SJD | 20,000 miles | American Airlines AAdvantage | 315 |
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.
Questions about business-class award flights from Chicago Midway (MDW) to Los Cabos (SJD)
What's the lowest business-class award from Chicago Midway (MDW) to Los Cabos (SJD)?
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 programs had business-class award space from Chicago Midway (MDW) to Los Cabos (SJD)?
American Airlines AAdvantage (6 dates) and United MileagePlus (9 dates), in the last 30 days.
Is there nonstop business-class award space from Chicago Midway (MDW) to Los Cabos (SJD)?
Yes. AwardTool observed nonstop business-class award space via American Airlines AAdvantage and United MileagePlus. The lowest nonstop award was 70,400 miles with United MileagePlus, which showed nonstop business-class space on 6 dates.