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Chicago → San Jose Cabo

Dec 21, 2026 · return Dec 31, 2026

ORD → SJD1 adulteconomyRound trip

8 flight options · 5 airlines

Nonstop flights

Mon, Dec 21 – Thu, Dec 31

American Airlines
8:55 amORD
4h 49m
Nonstop
12:44 pmSJD
American Airlines
1:44 pmSJD
4h 31m
Nonstop
7:15 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

United Airlines
9:03 amORD
5h
Nonstop
1:03 pmSJD
United Airlines
12:55 pmSJD
4h 16m
Nonstop
6:11 pmORD

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Thu, Dec 31

VB
12:35 amORD
7h 56m
MTY · 2h 30m
7:31 amSJD
United Airlines
12:55 pmSJD
4h 16m
Nonstop
6:11 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Delta Air Lines
6:20 amORD
7h 48m
MSP · 1h 40m
1:08 pmSJD
Delta Air Lines
2:04 pmSJD
8h 50m
ATL · 2h 50m
11:54 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Aeromexico
3:26 pmORD
8h 9m
MEX · 1h 15m
10:35 pmSJD
United Airlines
12:55 pmSJD
4h 16m
Nonstop
6:11 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

American Airlines
8:44 amORD
4h 58m
Nonstop
12:42 pmSJD
American Airlines
11:35 amSJD
7h 35m
AUS · 2h 5m
8:10 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

American Airlines
5:00 amORD
8h 14m
PHX · 2h 10m
12:14 pmSJD
American Airlines
1:44 pmSJD
4h 31m
Nonstop
7:15 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

United Airlines
7:00 amORD
8h 42m
DEN · 2h 44m
2:42 pmSJD
United Airlines
12:55 pmSJD
4h 16m
Nonstop
6:11 pmORD

Round-trip total · 1 adult · Taxes included

Make this trip yours

ORD ⇄ SJD

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 → 2026-12-31American AirlinesAA1649 / AA2636$739.502026-10-29T01:53:21Z
2026-12-21 → 2026-12-31United AirlinesUA1879 / UA766$754.002026-10-29T01:53:21Z
2026-12-21 → 2026-12-31VB / United AirlinesVB633 + VB4324 / UA766$616.252026-10-29T01:53:21Z
2026-12-21 → 2026-12-31Delta Air LinesDL1717 + DL1924 / DL1848 + DL1199$696.002026-10-29T01:53:21Z
2026-12-21 → 2026-12-31Aeromexico / United AirlinesAM687 + AM388 / UA766$714.132026-10-29T01:53:21Z
2026-12-21 → 2026-12-31American AirlinesAA1649 / AA2343 + AA2604$696.002026-10-29T01:53:21Z
2026-12-21 → 2026-12-31American AirlinesAA558 + AA2128 / AA2636$696.002026-10-29T01:53:21Z
2026-12-21 → 2026-12-31United AirlinesUA1217 + UA452 / UA766$710.502026-10-29T01:53:21Z

2026-12-21 → 2026-12-31 · $739.50

  • American Airlines AA1649: ORD 2026-12-21 08:55:00 → SJD 2026-12-21 12:44:00; nonstop; 289 minutes. Local airport times.
  • American Airlines AA2636: SJD 2026-12-31 13:44:00 → ORD 2026-12-31 19:15:00; nonstop; 271 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $754.00

  • United Airlines UA1879: ORD 2026-12-21 09:03:00 → SJD 2026-12-21 13:03:00; nonstop; 300 minutes. Local airport times.
  • United Airlines UA766: SJD 2026-12-31 12:55:00 → ORD 2026-12-31 18:11:00; nonstop; 256 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $616.25

  • VB VB633 / VB4324: ORD 2026-12-21 00:35:00 → SJD 2026-12-21 07:31:00; 1 stop(s) via MTY; 476 minutes. Local airport times.
    • VB633: ORD 2026-12-21 00:35:00 → MTY 2026-12-21 04:03:00; layover at MTY: 150 minutes.
    • VB4324: MTY 2026-12-21 06:33:00 → SJD 2026-12-21 07:31:00.
  • United Airlines UA766: SJD 2026-12-31 12:55:00 → ORD 2026-12-31 18:11:00; nonstop; 256 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $696.00

  • Delta Air Lines DL1717 / DL1924: ORD 2026-12-21 06:20:00 → SJD 2026-12-21 13:08:00; 1 stop(s) via MSP; 468 minutes. Local airport times.
    • DL1717: ORD 2026-12-21 06:20:00 → MSP 2026-12-21 07:54:00; layover at MSP: 100 minutes.
    • DL1924: MSP 2026-12-21 09:34:00 → SJD 2026-12-21 13:08:00.
  • Delta Air Lines DL1848 / DL1199: SJD 2026-12-31 14:04:00 → ORD 2026-12-31 23:54:00; 1 stop(s) via ATL; 530 minutes. Local airport times.
    • DL1848: SJD 2026-12-31 14:04:00 → ATL 2026-12-31 19:50:00; layover at ATL: 170 minutes.
    • DL1199: ATL 2026-12-31 22:40:00 → ORD 2026-12-31 23:54:00.

2026-12-21 → 2026-12-31 · $714.13

  • Aeromexico AM687 / AM388: ORD 2026-12-21 15:26:00 → SJD 2026-12-21 22:35:00; 1 stop(s) via MEX; 489 minutes. Local airport times.
    • AM687: ORD 2026-12-21 15:26:00 → MEX 2026-12-21 20:00:00; layover at MEX: 75 minutes.
    • AM388: MEX 2026-12-21 21:15:00 → SJD 2026-12-21 22:35:00.
  • United Airlines UA766: SJD 2026-12-31 12:55:00 → ORD 2026-12-31 18:11:00; nonstop; 256 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $696.00

  • American Airlines AA1649: ORD 2026-12-21 08:44:00 → SJD 2026-12-21 12:42:00; nonstop; 298 minutes. Local airport times.
  • American Airlines AA2343 / AA2604: SJD 2026-12-31 11:35:00 → ORD 2026-12-31 20:10:00; 1 stop(s) via AUS; 455 minutes. Local airport times.
    • AA2343: SJD 2026-12-31 11:35:00 → AUS 2026-12-31 15:05:00; layover at AUS: 125 minutes.
    • AA2604: AUS 2026-12-31 17:10:00 → ORD 2026-12-31 20:10:00.

2026-12-21 → 2026-12-31 · $696.00

  • American Airlines AA558 / AA2128: ORD 2026-12-21 05:00:00 → SJD 2026-12-21 12:14:00; 1 stop(s) via PHX; 494 minutes. Local airport times.
    • AA558: ORD 2026-12-21 05:00:00 → PHX 2026-12-21 07:49:00; layover at PHX: 130 minutes.
    • AA2128: PHX 2026-12-21 09:59:00 → SJD 2026-12-21 12:14:00.
  • American Airlines AA2636: SJD 2026-12-31 13:44:00 → ORD 2026-12-31 19:15:00; nonstop; 271 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $710.50

  • United Airlines UA1217 / UA452: ORD 2026-12-21 07:00:00 → SJD 2026-12-21 14:42:00; 1 stop(s) via DEN; 522 minutes. Local airport times.
    • UA1217: ORD 2026-12-21 07:00:00 → DEN 2026-12-21 08:46:00; layover at DEN: 164 minutes.
    • UA452: DEN 2026-12-21 11:30:00 → SJD 2026-12-21 14:42:00.
  • United Airlines UA766: SJD 2026-12-31 12:55:00 → ORD 2026-12-31 18:11:00; nonstop; 256 minutes. Local airport times.

More dates for this route