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San Juan → Chicago

Dec 21, 2026 · return Dec 28, 2026

SJU → ORD1 adulteconomyRound trip

10 flight options · 4 airlines

Nonstop flights

Mon, Dec 21 – Mon, Dec 28

American Airlines
3:52 pmSJU
5h 38m
Nonstop
7:30 pmORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
8:25 amSJU
5h 22m
Nonstop
11:47 amORD
United Airlines
2:16 pmORD
4h 44m
Nonstop
9:00 pmSJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
5:00 amSJU
5h 39m
Nonstop
8:39 amORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
4:55 pmSJU
5h 31m
Nonstop
8:26 pmORD
United Airlines
2:16 pmORD
4h 44m
Nonstop
9:00 pmSJU

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Mon, Dec 28

Frontier Airlines
5:19 amSJU
8h 41m
ATL · 2h 11m
12:00 pmORD
Frontier Airlines
4:42 pmORD
7h 45m
PHL · 1h 35m
2:27 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

DM
4:24 pmSJU
7h 56m
PUJ · 1h 45m
10:20 pmORD
DM
5:45 amORD
7h 18m
PUJ · 1h 28m
3:03 pmSJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Frontier Airlines
7:28 amSJU
8h 44m
PHL · 2h 3m
2:12 pmORD
Frontier Airlines
4:42 pmORD
7h 45m
PHL · 1h 35m
2:27 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Frontier Airlines
7:12 pmSJU
5h 9m
Nonstop
10:21 pmORD
Frontier Airlines
4:42 pmORD
7h 45m
PHL · 1h 35m
2:27 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
8:30 amSJU
9h 4m
PHL · 2h 15m
3:34 pmORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
8:05 amSJU
8h 33m
IAD · 2h 6m
2:38 pmORD
United Airlines
2:16 pmORD
4h 44m
Nonstop
9:00 pmSJU

Round-trip total · 1 adult · Taxes included

Make this trip yours

SJU ⇄ ORD

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
For AI assistants: every fare, every link, instructions

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 → 2026-12-28American AirlinesAA2279 / AA2571$563.752026-10-29T01:23:44Z
2026-12-21 → 2026-12-28United AirlinesUA2089 / UA695$577.502026-10-29T01:23:44Z
2026-12-21 → 2026-12-28Frontier AirlinesF92871 + F91441 / F92112 + F91726$316.252026-10-29T01:23:44Z
2026-12-21 → 2026-12-28DMDM1003 + DM5420 / DM5481 + DM1002$440.002026-10-29T01:23:44Z
2026-12-21 → 2026-12-28American AirlinesAA2436 / AA2571$563.752026-10-29T01:23:44Z
2026-12-21 → 2026-12-28United AirlinesUA2088 / UA695$577.502026-10-29T01:23:44Z
2026-12-21 → 2026-12-28Frontier AirlinesF91015 + F92113 / F92112 + F91726$316.252026-10-29T01:23:44Z
2026-12-21 → 2026-12-28Frontier AirlinesF93345 / F92112 + F91726$330.252026-10-29T01:23:44Z
2026-12-21 → 2026-12-28American AirlinesAA508 + AA595 / AA2571$539.252026-10-29T01:23:44Z
2026-12-21 → 2026-12-28United AirlinesUA2022 + UA2331 / UA695$553.002026-10-29T01:23:44Z

2026-12-21 → 2026-12-28 · $563.75

  • American Airlines AA2279: SJU 2026-12-21 15:52:00 → ORD 2026-12-21 19:30:00; nonstop; 338 minutes. Local airport times.
  • American Airlines AA2571: ORD 2026-12-28 23:00:00 → SJU 2026-12-29 05:36:00; nonstop; 276 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $577.50

  • United Airlines UA2089: SJU 2026-12-21 08:25:00 → ORD 2026-12-21 11:47:00; nonstop; 322 minutes. Local airport times.
  • United Airlines UA695: ORD 2026-12-28 14:16:00 → SJU 2026-12-28 21:00:00; nonstop; 284 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $316.25

  • Frontier Airlines F92871 / F91441: SJU 2026-12-21 05:19:00 → ORD 2026-12-21 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
    • F92871: SJU 2026-12-21 05:19:00 → ATL 2026-12-21 08:26:00; layover at ATL: 131 minutes.
    • F91441: ATL 2026-12-21 10:37:00 → ORD 2026-12-21 12:00:00.
  • Frontier Airlines F92112 / F91726: ORD 2026-12-28 16:42:00 → SJU 2026-12-29 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2026-12-28 16:42:00 → PHL 2026-12-28 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2026-12-28 21:39:00 → SJU 2026-12-29 02:27:00.

2026-12-21 → 2026-12-28 · $440.00

  • DM DM1003 / DM5420: SJU 2026-12-21 16:24:00 → ORD 2026-12-21 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-12-21 16:24:00 → PUJ 2026-12-21 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-12-21 19:10:00 → ORD 2026-12-21 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-12-28 05:45:00 → SJU 2026-12-28 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-12-28 05:45:00 → PUJ 2026-12-28 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-12-28 13:58:00 → SJU 2026-12-28 15:03:00.

2026-12-21 → 2026-12-28 · $563.75

  • American Airlines AA2436: SJU 2026-12-21 05:00:00 → ORD 2026-12-21 08:39:00; nonstop; 339 minutes. Local airport times.
  • American Airlines AA2571: ORD 2026-12-28 23:00:00 → SJU 2026-12-29 05:36:00; nonstop; 276 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $577.50

  • United Airlines UA2088: SJU 2026-12-21 16:55:00 → ORD 2026-12-21 20:26:00; nonstop; 331 minutes. Local airport times.
  • United Airlines UA695: ORD 2026-12-28 14:16:00 → SJU 2026-12-28 21:00:00; nonstop; 284 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $316.25

  • Frontier Airlines F91015 / F92113: SJU 2026-12-21 07:28:00 → ORD 2026-12-21 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
    • F91015: SJU 2026-12-21 07:28:00 → PHL 2026-12-21 10:36:00; layover at PHL: 123 minutes.
    • F92113: PHL 2026-12-21 12:39:00 → ORD 2026-12-21 14:12:00.
  • Frontier Airlines F92112 / F91726: ORD 2026-12-28 16:42:00 → SJU 2026-12-29 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2026-12-28 16:42:00 → PHL 2026-12-28 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2026-12-28 21:39:00 → SJU 2026-12-29 02:27:00.

2026-12-21 → 2026-12-28 · $330.25

  • Frontier Airlines F93345: SJU 2026-12-21 19:12:00 → ORD 2026-12-21 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F92112 / F91726: ORD 2026-12-28 16:42:00 → SJU 2026-12-29 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2026-12-28 16:42:00 → PHL 2026-12-28 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2026-12-28 21:39:00 → SJU 2026-12-29 02:27:00.

2026-12-21 → 2026-12-28 · $539.25

  • American Airlines AA508 / AA595: SJU 2026-12-21 08:30:00 → ORD 2026-12-21 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
    • AA508: SJU 2026-12-21 08:30:00 → PHL 2026-12-21 11:39:00; layover at PHL: 135 minutes.
    • AA595: PHL 2026-12-21 13:54:00 → ORD 2026-12-21 15:34:00.
  • American Airlines AA2571: ORD 2026-12-28 23:00:00 → SJU 2026-12-29 05:36:00; nonstop; 276 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $553.00

  • United Airlines UA2022 / UA2331: SJU 2026-12-21 08:05:00 → ORD 2026-12-21 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
    • UA2022: SJU 2026-12-21 08:05:00 → IAD 2026-12-21 11:09:00; layover at IAD: 126 minutes.
    • UA2331: IAD 2026-12-21 13:15:00 → ORD 2026-12-21 14:38:00.
  • United Airlines UA695: ORD 2026-12-28 14:16:00 → SJU 2026-12-28 21:00:00; nonstop; 284 minutes. Local airport times.

More dates for this route