Southwest Airlines stock forecast 2027–2029
MyStockButler's October 2026 analysis: Southwest Airlines’ weighted forecast is $26.79 in October 2027 and $30.23 in October 2029, with bear/base/bull probabilities of 30%, 52%, and 18%. It hinges on commercial gains becoming recurring operating profit and cash after fleet investment.
Where could Southwest Airlines’ shares be by 2029?
Weighted value is $26.79 in October 2027, implying a 31% total loss including dividends. It is $30.23 in October 2029, implying a 19% total loss. The bear case has 30% probability and the base case 52%; the bull case has 18%.
The probability-weighted price is $26.79 in October 2027, a 31% total loss including dividends. It rises to $31.08 in October 2028, still a 19% loss. It is $30.23 in October 2029, also a 19% loss. The final-date range runs from the bear case’s $15.25 to the bull case’s $39.96. Both sit against today’s $39.88.
| Case | Probability | October 2027 | October 2028 | October 2029 |
|---|---|---|---|---|
| Bear | 30 % | 0.00 (-98 %) | 16.76 (-55 %) | 15.25 (-59 %) |
| Base | 52 % | 37.95 (-3 %) | 36.49 (-5 %) | 35.51 (-6 %) |
| Bull | 18 % | 39.19 (+0 %) | 39.32 (+2 %) | 39.96 (+6 %) |
| Weighted | 100 % | 26.79 (-31 %) | 31.08 (-19 %) | 30.23 (-19 %) |
What has to go right, and what could go wrong for Southwest Airlines?
The drivers make the base recovery gradual, because commercial gains must overcome a weak operating record and heavy fleet spending.
| October 2027 | October 2028 | October 2029 | |
|---|---|---|---|
| Normal operating profit | 850 (-315 / 1,225) | 1,050 (325 / 1,665) | 1,170 (503 / 1,950) |
| Shares (millions) | 490 (490 / 488) | 490 (492 / 486) | 490 (494 / 484) |
| Dividends per share | 0.72 (0.72 / 0.72) | 0.72 (0.36 / 0.80) | 0.72 (0.18 / 0.88) |
| Enterprise value to normal operating profit | 25.60 (67.00 / 17.80) | 20.70 (43.50 / 13.10) | 18.60 (28.50 / 11.20) |
| Net debt | 3,185 (4,570 / 2,702) | 3,871 (5,891 / 2,721) | 4,382 (6,811 / 2,520) |
How much cash does Southwest Airlines really make?
The analytical “real free cash flow” measure also deducts $99 million of 2025 stock pay, producing negative $930 million. That is not a second cash payment; it recognizes the value transferred to employees. Aircraft disposals and sale-leasebacks can also supply cash, but they exchange ownership for future rent.
| 2025 | 2024 | 2023 | 2022 | 2021 | |
|---|---|---|---|---|---|
| Cash from operations | 1,842 | 462 | 3,164 | 3,790 | 2,322 |
| − Capital spending | 2,673 | 2,080 | 3,553 | 3,946 | 511 |
| = Free cash flow | -831 | -1,618 | -389 | -156 | 1,811 |
| − Stock pay | 99 | 45 | 86 | 84 | 58 |
| = Real free cash flow | -930 | -1,663 | -475 | -240 | 1,753 |
What does an investor pay today for Southwest Airlines?
Sales still grow, but 2025 operating margin was 1.5%, leaving little room for shocks. Real free cash flow, computed as cash from operations minus capital spending and stock pay, had a negative 3.3% margin. Diluted EPS was $0.79 against negative $1.67 of real free cash flow per share. A 13.2% share-count decline helped per-share results as dividends and buybacks exceeded free cash flow. The 9.6x next-twelve-month P/E sits below the 19.2x trailing P/E. Negative free-cash-flow yield was 4.3% beside a 13.1% buyback yield.