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Chicago → San Jose Cabo

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ORD → SJD1 adulteconomy

23 flight options · 5 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

American Airlines
8:44 amORD
4h 58m
Nonstop
12:42 pmSJD
American Airlines
1:44 pmSJD
4h 31m
Nonstop
7:15 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 20 – Mon, Nov 23

VB
12:35 amORD
7h 56m
MTY · 2h 30m
7:31 amSJD
United Airlines
2:30 pmSJD
8h 29m
DEN · 2h 44m
11:59 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

American Airlines
8:44 amORD
4h 58m
Nonstop
12:42 pmSJD
American Airlines
1:44 pmSJD
4h 31m
Nonstop
7:15 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 20 – Mon, Nov 23

United Airlines
7:00 amORD
8h 42m
DEN · 2h 44m
2:42 pmSJD
United Airlines
2:30 pmSJD
8h 29m
DEN · 2h 44m
11:59 pmORD

Round-trip total · 1 adult · Taxes included

Show 7 more flights

Fri, Nov 20 – Mon, Nov 23

American Airlines
8:55 amORD
4h 49m
Nonstop
12:44 pmSJD
American Airlines
11:35 amSJD
7h 35m
AUS · 2h 5m
8:10 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

American Airlines
12:05 pmORD
8h 44m
LAX · 1h 32m
7:49 pmSJD
American Airlines
1:44 pmSJD
4h 31m
Nonstop
7:15 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

American Airlines
12:05 pmORD
8h 44m
LAX · 1h 32m
7:49 pmSJD
American Airlines
1:44 pmSJD
4h 31m
Nonstop
7:15 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

American Airlines
8:55 amORD
4h 49m
Nonstop
12:44 pmSJD
American Airlines
11:35 amSJD
7h 35m
AUS · 2h 5m
8:10 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

United Airlines
9:03 amORD
5h
Nonstop
1:03 pmSJD
United Airlines
2:30 pmSJD
8h 29m
DEN · 2h 44m
11:59 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

One-way flights

Fri, Nov 20 · One way

American Airlines
8:44 amORD
4h 58m
Nonstop
12:42 pmSJD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

United Airlines
9:03 amORD
5h
Nonstop
1:03 pmSJD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

VB
12:35 amORD
7h 56m
MTY · 2h 30m
7:31 amSJD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Aeromexico
3:26 pmORD
8h 9m
MEX · 1h 15m
10:35 pmSJD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
6:20 amORD
7h 48m
MSP · 1h 40m
1:08 pmSJD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
12:05 pmORD
8h 44m
LAX · 1h 32m
7:49 pmSJD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
5:00 amORD
8h 14m
PHX · 2h 10m
12:14 pmSJD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

United Airlines
7:00 amORD
8h 42m
DEN · 2h 44m
2:42 pmSJD

One-way 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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  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
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Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 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)
2026-11-20 · one wayAmerican AirlinesAA1649$265.002026-10-29T01:53:21Z
2026-11-20 · one wayUnited AirlinesUA1879$270.002026-10-29T01:53:21Z
2026-11-20 → 2026-11-23American AirlinesAA1649 / AA2636$573.752026-10-29T01:53:21Z
2026-11-27 → 2026-12-04United AirlinesUA1879 / UA766$585.002026-10-29T01:53:21Z
2026-11-20 · one wayVBVB633 + VB4324$175.002026-10-29T01:53:21Z
2026-11-20 · one wayAeromexicoAM687 + AM388$250.002026-10-29T01:53:21Z
2026-11-20 · one wayDelta Air LinesDL1717 + DL1924$255.002026-10-29T01:53:21Z
2026-11-20 → 2026-11-23VB / United AirlinesVB633 + VB4324 / UA2152 + UA1787$452.502026-10-29T01:53:21Z
2026-11-27 → 2026-12-04Delta Air LinesDL1717 + DL1924 / DL1848 + DL1199$540.002026-10-29T01:53:21Z
2026-11-27 → 2026-12-04Aeromexico / United AirlinesAM687 + AM388 / UA766$550.632026-10-29T01:53:21Z
2026-11-27 → 2026-12-04American AirlinesAA1649 / AA2636$573.752026-10-29T01:53:21Z
2026-11-20 · one wayAmerican AirlinesAA832 + AS1384$235.002026-10-29T01:53:21Z
2026-11-20 · one wayAmerican AirlinesAA558 + AA2128$235.002026-10-29T01:53:21Z
2026-11-20 · one wayUnited AirlinesUA1217 + UA452$240.002026-10-29T01:53:21Z
2026-11-27 → 2026-12-04VB / United AirlinesVB633 + VB4324 / UA766$466.252026-10-29T01:53:21Z
2026-11-20 → 2026-11-23United AirlinesUA1217 + UA452 / UA2152 + UA1787$517.502026-10-29T01:53:21Z
2026-11-20 → 2026-11-23American AirlinesAA1649 / AA2343 + AA2604$536.252026-10-29T01:53:21Z
2026-11-27 → 2026-12-04American AirlinesAA832 + AS1384 / AA2636$536.252026-10-29T01:53:21Z
2026-11-20 → 2026-11-23Delta Air LinesDL1717 + DL1924 / DL1848 + DL1199$540.002026-10-29T01:53:21Z
2026-11-20 → 2026-11-23American AirlinesAA832 + AS1384 / AA2636$543.752026-10-29T01:53:21Z
2026-11-27 → 2026-12-04American AirlinesAA1649 / AA2343 + AA2604$543.752026-10-29T01:53:21Z
2026-11-20 → 2026-11-23United AirlinesUA1879 / UA2152 + UA1787$547.502026-10-29T01:53:21Z
2026-11-27 → 2026-12-04United AirlinesUA1217 + UA452 / UA766$547.502026-10-29T01:53:21Z

2026-11-20 · one way · $265.00

  • American Airlines AA1649: ORD 2026-11-20 08:44:00 → SJD 2026-11-20 12:42:00; nonstop; 298 minutes. Local airport times.

2026-11-20 · one way · $270.00

  • United Airlines UA1879: ORD 2026-11-20 09:03:00 → SJD 2026-11-20 13:03:00; nonstop; 300 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $573.75

  • American Airlines AA1649: ORD 2026-11-20 08:44:00 → SJD 2026-11-20 12:42:00; nonstop; 298 minutes. Local airport times.
  • American Airlines AA2636: SJD 2026-11-23 13:44:00 → ORD 2026-11-23 19:15:00; nonstop; 271 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $585.00

  • United Airlines UA1879: ORD 2026-11-27 09:03:00 → SJD 2026-11-27 13:03:00; nonstop; 300 minutes. Local airport times.
  • United Airlines UA766: SJD 2026-12-04 12:55:00 → ORD 2026-12-04 18:11:00; nonstop; 256 minutes. Local airport times.

2026-11-20 · one way · $175.00

  • VB VB633 / VB4324: ORD 2026-11-20 00:35:00 → SJD 2026-11-20 07:31:00; 1 stop(s) via MTY; 476 minutes. Local airport times.
    • VB633: ORD 2026-11-20 00:35:00 → MTY 2026-11-20 04:03:00; layover at MTY: 150 minutes.
    • VB4324: MTY 2026-11-20 06:33:00 → SJD 2026-11-20 07:31:00.

2026-11-20 · one way · $250.00

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

2026-11-20 · one way · $255.00

  • Delta Air Lines DL1717 / DL1924: ORD 2026-11-20 06:20:00 → SJD 2026-11-20 13:08:00; 1 stop(s) via MSP; 468 minutes. Local airport times.
    • DL1717: ORD 2026-11-20 06:20:00 → MSP 2026-11-20 07:54:00; layover at MSP: 100 minutes.
    • DL1924: MSP 2026-11-20 09:34:00 → SJD 2026-11-20 13:08:00.

2026-11-20 → 2026-11-23 · $452.50

  • VB VB633 / VB4324: ORD 2026-11-20 00:35:00 → SJD 2026-11-20 07:31:00; 1 stop(s) via MTY; 476 minutes. Local airport times.
    • VB633: ORD 2026-11-20 00:35:00 → MTY 2026-11-20 04:03:00; layover at MTY: 150 minutes.
    • VB4324: MTY 2026-11-20 06:33:00 → SJD 2026-11-20 07:31:00.
  • United Airlines UA2152 / UA1787: SJD 2026-11-23 14:30:00 → ORD 2026-11-23 23:59:00; 1 stop(s) via DEN; 509 minutes. Local airport times.
    • UA2152: SJD 2026-11-23 14:30:00 → DEN 2026-11-23 17:41:00; layover at DEN: 164 minutes.
    • UA1787: DEN 2026-11-23 20:25:00 → ORD 2026-11-23 23:59:00.

2026-11-27 → 2026-12-04 · $540.00

  • Delta Air Lines DL1717 / DL1924: ORD 2026-11-27 06:20:00 → SJD 2026-11-27 13:08:00; 1 stop(s) via MSP; 468 minutes. Local airport times.
    • DL1717: ORD 2026-11-27 06:20:00 → MSP 2026-11-27 07:54:00; layover at MSP: 100 minutes.
    • DL1924: MSP 2026-11-27 09:34:00 → SJD 2026-11-27 13:08:00.
  • Delta Air Lines DL1848 / DL1199: SJD 2026-12-04 14:04:00 → ORD 2026-12-04 23:54:00; 1 stop(s) via ATL; 530 minutes. Local airport times.
    • DL1848: SJD 2026-12-04 14:04:00 → ATL 2026-12-04 19:50:00; layover at ATL: 170 minutes.
    • DL1199: ATL 2026-12-04 22:40:00 → ORD 2026-12-04 23:54:00.

2026-11-27 → 2026-12-04 · $550.63

  • Aeromexico AM687 / AM388: ORD 2026-11-27 15:26:00 → SJD 2026-11-27 22:35:00; 1 stop(s) via MEX; 489 minutes. Local airport times.
    • AM687: ORD 2026-11-27 15:26:00 → MEX 2026-11-27 20:00:00; layover at MEX: 75 minutes.
    • AM388: MEX 2026-11-27 21:15:00 → SJD 2026-11-27 22:35:00.
  • United Airlines UA766: SJD 2026-12-04 12:55:00 → ORD 2026-12-04 18:11:00; nonstop; 256 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $573.75

  • American Airlines AA1649: ORD 2026-11-27 08:44:00 → SJD 2026-11-27 12:42:00; nonstop; 298 minutes. Local airport times.
  • American Airlines AA2636: SJD 2026-12-04 13:44:00 → ORD 2026-12-04 19:15:00; nonstop; 271 minutes. Local airport times.

2026-11-20 · one way · $235.00

  • American Airlines AA832 / AS1384: ORD 2026-11-20 12:05:00 → SJD 2026-11-20 19:49:00; 1 stop(s) via LAX; 524 minutes. Local airport times.
    • AA832: ORD 2026-11-20 12:05:00 → LAX 2026-11-20 14:48:00; layover at LAX: 92 minutes.
    • AS1384: LAX 2026-11-20 16:20:00 → SJD 2026-11-20 19:49:00.

2026-11-20 · one way · $235.00

  • American Airlines AA558 / AA2128: ORD 2026-11-20 05:00:00 → SJD 2026-11-20 12:14:00; 1 stop(s) via PHX; 494 minutes. Local airport times.
    • AA558: ORD 2026-11-20 05:00:00 → PHX 2026-11-20 07:49:00; layover at PHX: 130 minutes.
    • AA2128: PHX 2026-11-20 09:59:00 → SJD 2026-11-20 12:14:00.

2026-11-20 · one way · $240.00

  • United Airlines UA1217 / UA452: ORD 2026-11-20 07:00:00 → SJD 2026-11-20 14:42:00; 1 stop(s) via DEN; 522 minutes. Local airport times.
    • UA1217: ORD 2026-11-20 07:00:00 → DEN 2026-11-20 08:46:00; layover at DEN: 164 minutes.
    • UA452: DEN 2026-11-20 11:30:00 → SJD 2026-11-20 14:42:00.

2026-11-27 → 2026-12-04 · $466.25

  • VB VB633 / VB4324: ORD 2026-11-27 00:35:00 → SJD 2026-11-27 07:31:00; 1 stop(s) via MTY; 476 minutes. Local airport times.
    • VB633: ORD 2026-11-27 00:35:00 → MTY 2026-11-27 04:03:00; layover at MTY: 150 minutes.
    • VB4324: MTY 2026-11-27 06:33:00 → SJD 2026-11-27 07:31:00.
  • United Airlines UA766: SJD 2026-12-04 12:55:00 → ORD 2026-12-04 18:11:00; nonstop; 256 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $517.50

  • United Airlines UA1217 / UA452: ORD 2026-11-20 07:00:00 → SJD 2026-11-20 14:42:00; 1 stop(s) via DEN; 522 minutes. Local airport times.
    • UA1217: ORD 2026-11-20 07:00:00 → DEN 2026-11-20 08:46:00; layover at DEN: 164 minutes.
    • UA452: DEN 2026-11-20 11:30:00 → SJD 2026-11-20 14:42:00.
  • United Airlines UA2152 / UA1787: SJD 2026-11-23 14:30:00 → ORD 2026-11-23 23:59:00; 1 stop(s) via DEN; 509 minutes. Local airport times.
    • UA2152: SJD 2026-11-23 14:30:00 → DEN 2026-11-23 17:41:00; layover at DEN: 164 minutes.
    • UA1787: DEN 2026-11-23 20:25:00 → ORD 2026-11-23 23:59:00.

2026-11-20 → 2026-11-23 · $536.25

  • American Airlines AA1649: ORD 2026-11-20 08:55:00 → SJD 2026-11-20 12:44:00; nonstop; 289 minutes. Local airport times.
  • American Airlines AA2343 / AA2604: SJD 2026-11-23 11:35:00 → ORD 2026-11-23 20:10:00; 1 stop(s) via AUS; 455 minutes. Local airport times.
    • AA2343: SJD 2026-11-23 11:35:00 → AUS 2026-11-23 15:05:00; layover at AUS: 125 minutes.
    • AA2604: AUS 2026-11-23 17:10:00 → ORD 2026-11-23 20:10:00.

2026-11-27 → 2026-12-04 · $536.25

  • American Airlines AA832 / AS1384: ORD 2026-11-27 12:05:00 → SJD 2026-11-27 19:49:00; 1 stop(s) via LAX; 524 minutes. Local airport times.
    • AA832: ORD 2026-11-27 12:05:00 → LAX 2026-11-27 14:48:00; layover at LAX: 92 minutes.
    • AS1384: LAX 2026-11-27 16:20:00 → SJD 2026-11-27 19:49:00.
  • American Airlines AA2636: SJD 2026-12-04 13:44:00 → ORD 2026-12-04 19:15:00; nonstop; 271 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $540.00

  • Delta Air Lines DL1717 / DL1924: ORD 2026-11-20 06:20:00 → SJD 2026-11-20 13:08:00; 1 stop(s) via MSP; 468 minutes. Local airport times.
    • DL1717: ORD 2026-11-20 06:20:00 → MSP 2026-11-20 07:54:00; layover at MSP: 100 minutes.
    • DL1924: MSP 2026-11-20 09:34:00 → SJD 2026-11-20 13:08:00.
  • Delta Air Lines DL1848 / DL1199: SJD 2026-11-23 14:04:00 → ORD 2026-11-23 23:54:00; 1 stop(s) via ATL; 530 minutes. Local airport times.
    • DL1848: SJD 2026-11-23 14:04:00 → ATL 2026-11-23 19:50:00; layover at ATL: 170 minutes.
    • DL1199: ATL 2026-11-23 22:40:00 → ORD 2026-11-23 23:54:00.

2026-11-20 → 2026-11-23 · $543.75

  • American Airlines AA832 / AS1384: ORD 2026-11-20 12:05:00 → SJD 2026-11-20 19:49:00; 1 stop(s) via LAX; 524 minutes. Local airport times.
    • AA832: ORD 2026-11-20 12:05:00 → LAX 2026-11-20 14:48:00; layover at LAX: 92 minutes.
    • AS1384: LAX 2026-11-20 16:20:00 → SJD 2026-11-20 19:49:00.
  • American Airlines AA2636: SJD 2026-11-23 13:44:00 → ORD 2026-11-23 19:15:00; nonstop; 271 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $543.75

  • American Airlines AA1649: ORD 2026-11-27 08:55:00 → SJD 2026-11-27 12:44:00; nonstop; 289 minutes. Local airport times.
  • American Airlines AA2343 / AA2604: SJD 2026-12-04 11:35:00 → ORD 2026-12-04 20:10:00; 1 stop(s) via AUS; 455 minutes. Local airport times.
    • AA2343: SJD 2026-12-04 11:35:00 → AUS 2026-12-04 15:05:00; layover at AUS: 125 minutes.
    • AA2604: AUS 2026-12-04 17:10:00 → ORD 2026-12-04 20:10:00.

2026-11-20 → 2026-11-23 · $547.50

  • United Airlines UA1879: ORD 2026-11-20 09:03:00 → SJD 2026-11-20 13:03:00; nonstop; 300 minutes. Local airport times.
  • United Airlines UA2152 / UA1787: SJD 2026-11-23 14:30:00 → ORD 2026-11-23 23:59:00; 1 stop(s) via DEN; 509 minutes. Local airport times.
    • UA2152: SJD 2026-11-23 14:30:00 → DEN 2026-11-23 17:41:00; layover at DEN: 164 minutes.
    • UA1787: DEN 2026-11-23 20:25:00 → ORD 2026-11-23 23:59:00.

2026-11-27 → 2026-12-04 · $547.50

  • United Airlines UA1217 / UA452: ORD 2026-11-27 07:00:00 → SJD 2026-11-27 14:42:00; 1 stop(s) via DEN; 522 minutes. Local airport times.
    • UA1217: ORD 2026-11-27 07:00:00 → DEN 2026-11-27 08:46:00; layover at DEN: 164 minutes.
    • UA452: DEN 2026-11-27 11:30:00 → SJD 2026-11-27 14:42:00.
  • United Airlines UA766: SJD 2026-12-04 12:55:00 → ORD 2026-12-04 18:11:00; nonstop; 256 minutes. Local airport times.

More dates for this route