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Chicago → San Juan

Dec 21, 2026 · return Dec 26, 2026

ORD → SJU1 adulteconomyRound trip

11 flight options · 5 airlines

Nonstop flights

Mon, Dec 21 – Sat, Dec 26

Frontier Airlines
11:53 pmORD
4h 39m
Nonstop
6:32 am+1SJU
Frontier Airlines
10:26 pmSJU
5h 7m
Nonstop
1:33 am+1ORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

United Airlines
8:52 amORD
4h 48m
Nonstop
3:40 pmSJU
United Airlines
8:25 amSJU
5h 22m
Nonstop
11:47 amORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

American Airlines
8:15 amORD
4h 38m
Nonstop
2:53 pmSJU
American Airlines
5:00 amSJU
5h 39m
Nonstop
8:39 amORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

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

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Sat, Dec 26

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

Delta Air Lines
8:04 amORD
7h 42m
ATL · 2h 21m
5:46 pmSJU
Delta Air Lines
2:55 pmSJU
9h 41m
BOS · 2h 29m
10:36 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

Frontier Airlines
4:42 pmORD
7h 45m
PHL · 1h 35m
2:27 am+1SJU
Frontier Airlines
10:26 pmSJU
5h 7m
Nonstop
1:33 am+1ORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

American Airlines
12:05 pmORD
7h 8m
CLT · 1h 25m
9:13 pmSJU
American Airlines
5:00 amSJU
5h 39m
Nonstop
8:39 amORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

Delta Air Lines
6:00 amORD
8h 56m
JFK · 2h 50m
4:56 pmSJU
Delta Air Lines
2:55 pmSJU
9h 41m
BOS · 2h 29m
10:36 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

United Airlines
1:00 pmORD
7h 22m
IAD · 1h 26m
10:22 pmSJU
United Airlines
8:25 amSJU
5h 22m
Nonstop
11:47 amORD

Round-trip total · 1 adult · Taxes included

Make this trip yours

ORD ⇄ SJU

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 → 2026-12-26Frontier AirlinesF93346 / F94789$391.502026-10-29T01:53:25Z
2026-12-21 → 2026-12-26American AirlinesAA2571 / AA2436$623.502026-10-29T01:53:25Z
2026-12-21 → 2026-12-26United AirlinesUA1996 / UA2089$652.502026-10-29T01:53:25Z
2026-12-21 → 2026-12-26DMDM5481 + DM1002 / DM1003 + DM5420$522.002026-10-29T01:53:25Z
2026-12-21 → 2026-12-26Delta Air LinesDL1687 + DL1946 / DL1780 + DL2804$609.002026-10-29T01:53:25Z
2026-12-21 → 2026-12-26American AirlinesAA2213 / AA2436$623.502026-10-29T01:53:25Z
2026-12-21 → 2026-12-26United AirlinesUA695 / UA2089$652.502026-10-29T01:53:25Z
2026-12-21 → 2026-12-26Frontier AirlinesF92112 + F91726 / F94789$377.002026-10-29T01:53:25Z
2026-12-21 → 2026-12-26American AirlinesAA1889 + AA2098 / AA2436$594.502026-10-29T01:53:25Z
2026-12-21 → 2026-12-26Delta Air LinesDL5666 + DL1961 / DL1780 + DL2804$609.002026-10-29T01:53:25Z
2026-12-21 → 2026-12-26United AirlinesUA1128 + UA2025 / UA2089$623.502026-10-29T01:53:25Z

2026-12-21 → 2026-12-26 · $391.50

  • Frontier Airlines F93346: ORD 2026-12-21 23:53:00 → SJU 2026-12-22 06:32:00; nonstop; 279 minutes. Local airport times.
  • Frontier Airlines F94789: SJU 2026-12-26 22:26:00 → ORD 2026-12-27 01:33:00; nonstop; 307 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $623.50

  • American Airlines AA2571: ORD 2026-12-21 23:00:00 → SJU 2026-12-22 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2436: SJU 2026-12-26 05:00:00 → ORD 2026-12-26 08:39:00; nonstop; 339 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $652.50

  • United Airlines UA1996: ORD 2026-12-21 08:52:00 → SJU 2026-12-21 15:40:00; nonstop; 288 minutes. Local airport times.
  • United Airlines UA2089: SJU 2026-12-26 08:25:00 → ORD 2026-12-26 11:47:00; nonstop; 322 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $522.00

  • DM DM5481 / DM1002: ORD 2026-12-21 05:45:00 → SJU 2026-12-21 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-12-21 05:45:00 → PUJ 2026-12-21 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-12-21 13:58:00 → SJU 2026-12-21 15:03:00.
  • DM DM1003 / DM5420: SJU 2026-12-26 16:24:00 → ORD 2026-12-26 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-12-26 16:24:00 → PUJ 2026-12-26 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-12-26 19:10:00 → ORD 2026-12-26 22:20:00.

2026-12-21 → 2026-12-26 · $609.00

  • Delta Air Lines DL1687 / DL1946: ORD 2026-12-21 08:04:00 → SJU 2026-12-21 17:46:00; 1 stop(s) via ATL; 462 minutes. Local airport times.
    • DL1687: ORD 2026-12-21 08:04:00 → ATL 2026-12-21 11:00:00; layover at ATL: 141 minutes.
    • DL1946: ATL 2026-12-21 13:21:00 → SJU 2026-12-21 17:46:00.
  • Delta Air Lines DL1780 / DL2804: SJU 2026-12-26 14:55:00 → ORD 2026-12-26 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
    • DL1780: SJU 2026-12-26 14:55:00 → BOS 2026-12-26 18:11:00; layover at BOS: 149 minutes.
    • DL2804: BOS 2026-12-26 20:40:00 → ORD 2026-12-26 22:36:00.

2026-12-21 → 2026-12-26 · $623.50

  • American Airlines AA2213: ORD 2026-12-21 08:15:00 → SJU 2026-12-21 14:53:00; nonstop; 278 minutes. Local airport times.
  • American Airlines AA2436: SJU 2026-12-26 05:00:00 → ORD 2026-12-26 08:39:00; nonstop; 339 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $652.50

  • United Airlines UA695: ORD 2026-12-21 14:16:00 → SJU 2026-12-21 21:00:00; nonstop; 284 minutes. Local airport times.
  • United Airlines UA2089: SJU 2026-12-26 08:25:00 → ORD 2026-12-26 11:47:00; nonstop; 322 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $377.00

  • Frontier Airlines F92112 / F91726: ORD 2026-12-21 16:42:00 → SJU 2026-12-22 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2026-12-21 16:42:00 → PHL 2026-12-21 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2026-12-21 21:39:00 → SJU 2026-12-22 02:27:00.
  • Frontier Airlines F94789: SJU 2026-12-26 22:26:00 → ORD 2026-12-27 01:33:00; nonstop; 307 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $594.50

  • American Airlines AA1889 / AA2098: ORD 2026-12-21 12:05:00 → SJU 2026-12-21 21:13:00; 1 stop(s) via CLT; 428 minutes. Local airport times.
    • AA1889: ORD 2026-12-21 12:05:00 → CLT 2026-12-21 15:10:00; layover at CLT: 85 minutes.
    • AA2098: CLT 2026-12-21 16:35:00 → SJU 2026-12-21 21:13:00.
  • American Airlines AA2436: SJU 2026-12-26 05:00:00 → ORD 2026-12-26 08:39:00; nonstop; 339 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $609.00

  • Delta Air Lines DL5666 / DL1961: ORD 2026-12-21 06:00:00 → SJU 2026-12-21 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
    • DL5666: ORD 2026-12-21 06:00:00 → JFK 2026-12-21 09:20:00; layover at JFK: 170 minutes.
    • DL1961: JFK 2026-12-21 12:10:00 → SJU 2026-12-21 16:56:00.
  • Delta Air Lines DL1780 / DL2804: SJU 2026-12-26 14:55:00 → ORD 2026-12-26 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
    • DL1780: SJU 2026-12-26 14:55:00 → BOS 2026-12-26 18:11:00; layover at BOS: 149 minutes.
    • DL2804: BOS 2026-12-26 20:40:00 → ORD 2026-12-26 22:36:00.

2026-12-21 → 2026-12-26 · $623.50

  • United Airlines UA1128 / UA2025: ORD 2026-12-21 13:00:00 → SJU 2026-12-21 22:22:00; 1 stop(s) via IAD; 442 minutes. Local airport times.
    • UA1128: ORD 2026-12-21 13:00:00 → IAD 2026-12-21 16:03:00; layover at IAD: 86 minutes.
    • UA2025: IAD 2026-12-21 17:29:00 → SJU 2026-12-21 22:22:00.
  • United Airlines UA2089: SJU 2026-12-26 08:25:00 → ORD 2026-12-26 11:47:00; nonstop; 322 minutes. Local airport times.

More dates for this route