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San Juan → Chicago

Dec 21, 2026 · return Dec 27, 2026

SJU → MDW1 adulteconomyRound trip

5 flight options · 2 airlines

One-stop flights

Mon, Dec 21 – Sun, Dec 27

Frontier Airlines
5:01 amSJU
8h 32m
ATL · 2h 5m
11:33 amMDW
Frontier Airlines
1:11 pmMDW
8h 33m
ATL · 2h 48m
11:44 pmSJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
2:05 pmSJU
8h 10m
BWI · 2h
8:15 pmMDW
Southwest Airlines
2:30 pmMDW
7h 5m
BNA · 1h 35m
11:35 pmSJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
5:35 amSJU
8h 30m
MCO · 2h 25m
12:05 pmMDW
Southwest Airlines
2:30 pmMDW
7h 5m
BNA · 1h 35m
11:35 pmSJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
6:05 amSJU
8h 55m
TPA · 2h 55m
1:00 pmMDW
Southwest Airlines
2:30 pmMDW
7h 5m
BNA · 1h 35m
11:35 pmSJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
3:30 pmSJU
5h 10m
Nonstop
6:40 pmMDW
Southwest Airlines
2:30 pmMDW
7h 5m
BNA · 1h 35m
11:35 pmSJU

Round-trip total · 1 adult · Taxes included

Make this trip yours

SJU ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2026-12-27Frontier AirlinesF92871 + F92779 / F92144 + F92300$399.002026-10-29T01:23:44Z
2026-12-21 → 2026-12-27Southwest AirlinesWN4916 + WN1072 / WN2938 + WN2898$553.002026-10-29T01:23:44Z
2026-12-21 → 2026-12-27Southwest AirlinesWN4666 + WN2803 / WN2938 + WN2898$553.002026-10-29T01:23:44Z
2026-12-21 → 2026-12-27Southwest AirlinesWN3957 + WN1854 / WN2938 + WN2898$553.002026-10-29T01:23:44Z
2026-12-21 → 2026-12-27Southwest AirlinesWN3881 / WN2938 + WN2898$581.002026-10-29T01:23:44Z

2026-12-21 → 2026-12-27 · $399.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-21 05:01:00 → MDW 2026-12-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-21 05:01:00 → ATL 2026-12-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-21 10:27:00 → MDW 2026-12-21 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-27 13:11:00 → SJU 2026-12-27 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-27 13:11:00 → ATL 2026-12-27 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-27 19:06:00 → SJU 2026-12-27 23:44:00.

2026-12-21 → 2026-12-27 · $553.00

  • Southwest Airlines WN4916 / WN1072: SJU 2026-12-21 14:05:00 → MDW 2026-12-21 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
    • WN4916: SJU 2026-12-21 14:05:00 → BWI 2026-12-21 17:10:00; layover at BWI: 120 minutes.
    • WN1072: BWI 2026-12-21 19:10:00 → MDW 2026-12-21 20:15:00.
  • Southwest Airlines WN2938 / WN2898: MDW 2026-12-27 14:30:00 → SJU 2026-12-27 23:35:00; 1 stop(s) via BNA; 425 minutes. Local airport times.
    • WN2938: MDW 2026-12-27 14:30:00 → BNA 2026-12-27 16:00:00; layover at BNA: 95 minutes.
    • WN2898: BNA 2026-12-27 17:35:00 → SJU 2026-12-27 23:35:00.

2026-12-21 → 2026-12-27 · $553.00

  • Southwest Airlines WN4666 / WN2803: SJU 2026-12-21 05:35:00 → MDW 2026-12-21 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-12-21 05:35:00 → MCO 2026-12-21 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-12-21 10:10:00 → MDW 2026-12-21 12:05:00.
  • Southwest Airlines WN2938 / WN2898: MDW 2026-12-27 14:30:00 → SJU 2026-12-27 23:35:00; 1 stop(s) via BNA; 425 minutes. Local airport times.
    • WN2938: MDW 2026-12-27 14:30:00 → BNA 2026-12-27 16:00:00; layover at BNA: 95 minutes.
    • WN2898: BNA 2026-12-27 17:35:00 → SJU 2026-12-27 23:35:00.

2026-12-21 → 2026-12-27 · $553.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-21 06:05:00 → MDW 2026-12-21 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-21 06:05:00 → TPA 2026-12-21 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-21 11:15:00 → MDW 2026-12-21 13:00:00.
  • Southwest Airlines WN2938 / WN2898: MDW 2026-12-27 14:30:00 → SJU 2026-12-27 23:35:00; 1 stop(s) via BNA; 425 minutes. Local airport times.
    • WN2938: MDW 2026-12-27 14:30:00 → BNA 2026-12-27 16:00:00; layover at BNA: 95 minutes.
    • WN2898: BNA 2026-12-27 17:35:00 → SJU 2026-12-27 23:35:00.

2026-12-21 → 2026-12-27 · $581.00

  • Southwest Airlines WN3881: SJU 2026-12-21 15:30:00 → MDW 2026-12-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • Southwest Airlines WN2938 / WN2898: MDW 2026-12-27 14:30:00 → SJU 2026-12-27 23:35:00; 1 stop(s) via BNA; 425 minutes. Local airport times.
    • WN2938: MDW 2026-12-27 14:30:00 → BNA 2026-12-27 16:00:00; layover at BNA: 95 minutes.
    • WN2898: BNA 2026-12-27 17:35:00 → SJU 2026-12-27 23:35:00.

More dates for this route