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Chicago → San Jose

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ORD → SJO1 adulteconomy

18 flight options · 4 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Avianca
2:20 pmORD
8h 55m
GUA · 2h 55m
11:15 pmSJO
Avianca
10:00 amSJO
8h 15m
GUA · 1h 58m
6:15 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Frontier Airlines
5:01 amORD
7h 40m
MCO · 1h 25m
12:41 pmSJO
United Airlines
1:25 pmSJO
5h 32m
Nonstop
6:57 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
6:05 amORD
8h 30m
MIA · 2h 3m
2:35 pmSJO
American Airlines
3:54 pmSJO
8h 59m
MIA · 2h 14m
12:53 am+1ORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

United Airlines
12:40 pmORD
7h 59m
IAH · 1h 16m
8:39 pmSJO
United Airlines
1:25 pmSJO
5h 32m
Nonstop
6:57 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Avianca
2:20 pmORD
8h 55m
GUA · 2h 55m
11:15 pmSJO
Avianca
10:00 amSJO
8h 15m
GUA · 1h 58m
6:15 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Frontier Airlines
5:58 amORD
8h 18m
ATL · 1h 47m
2:16 pmSJO
United Airlines
1:25 pmSJO
5h 32m
Nonstop
6:57 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Frontier Airlines
5:01 amORD
7h 40m
MCO · 1h 25m
12:41 pmSJO
United Airlines
1:25 pmSJO
5h 32m
Nonstop
6:57 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Frontier Airlines
5:58 amORD
8h 18m
ATL · 1h 47m
2:16 pmSJO
United Airlines
1:25 pmSJO
5h 32m
Nonstop
6:57 pmORD

Round-trip total · 1 adult · Taxes included

Show 4 more flights

Fri, Nov 27 – Fri, Dec 4

American Airlines
6:05 amORD
8h 30m
MIA · 2h 3m
2:35 pmSJO
American Airlines
3:54 pmSJO
8h 59m
MIA · 2h 14m
12:53 am+1ORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

United Airlines
10:39 amORD
9h 14m
EWR · 1h 35m
7:53 pmSJO
United Airlines
1:25 pmSJO
5h 32m
Nonstop
6:57 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

United Airlines
10:39 amORD
9h 14m
EWR · 1h 35m
7:53 pmSJO
United Airlines
1:25 pmSJO
5h 32m
Nonstop
6:57 pmORD

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

United Airlines
12:40 pmORD
7h 59m
IAH · 1h 16m
8:39 pmSJO
United Airlines
1:25 pmSJO
5h 32m
Nonstop
6:57 pmORD

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Frontier Airlines
5:01 amORD
7h 40m
MCO · 1h 25m
12:41 pmSJO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Avianca
2:20 pmORD
8h 55m
GUA · 2h 55m
11:15 pmSJO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
6:05 amORD
8h 30m
MIA · 2h 3m
2:35 pmSJO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

United Airlines
10:39 amORD
9h 14m
EWR · 1h 35m
7:53 pmSJO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Frontier Airlines
5:58 amORD
8h 18m
ATL · 1h 47m
2:16 pmSJO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

United Airlines
12:40 pmORD
7h 59m
IAH · 1h 16m
8:39 pmSJO

One-way total · 1 adult · Taxes included

Make this trip yours

ORD ⇄ SJO

Economy

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

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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 wayFrontier AirlinesF91901 + F935$147.252026-10-29T01:53:24Z
2026-11-20 · one wayAviancaAV631 + AV641$190.002026-10-29T01:53:24Z
2026-11-20 · one wayAmerican AirlinesAA884 + AA310$232.752026-10-29T01:53:24Z
2026-11-20 · one wayUnited AirlinesUA1856 + UA1222$237.502026-10-29T01:53:24Z
2026-11-20 → 2026-11-23AviancaAV631 + AV641 / AV628 + UA2007$418.002026-10-29T01:53:24Z
2026-11-27 → 2026-12-04Frontier Airlines / United AirlinesF91901 + F935 / UA1952$461.702026-10-29T01:53:24Z
2026-11-20 → 2026-11-23American AirlinesAA884 + AA310 / AA318 + AA3320$512.052026-10-29T01:53:24Z
2026-11-20 → 2026-11-23United AirlinesUA1544 + UA1280 / UA1952$557.652026-10-29T01:53:24Z
2026-11-20 · one wayFrontier AirlinesF91596 + F9215$147.252026-10-29T01:53:24Z
2026-11-20 · one wayUnited AirlinesUA1544 + UA1280$237.502026-10-29T01:53:24Z
2026-11-27 → 2026-12-04AviancaAV631 + AV641 / AV628 + UA2007$428.002026-10-29T01:53:24Z
2026-11-27 → 2026-12-04Frontier Airlines / United AirlinesF91596 + F9215 / UA1952$461.702026-10-29T01:53:24Z
2026-11-20 → 2026-11-23Frontier Airlines / United AirlinesF91901 + F935 / UA1952$472.152026-10-29T01:53:24Z
2026-11-20 → 2026-11-23Frontier Airlines / United AirlinesF91596 + F9215 / UA1952$472.152026-10-29T01:53:24Z
2026-11-27 → 2026-12-04American AirlinesAA884 + AA310 / AA318 + AA3320$524.302026-10-29T01:53:24Z
2026-11-20 → 2026-11-23United AirlinesUA1856 + UA1222 / UA1952$557.652026-10-29T01:53:24Z
2026-11-27 → 2026-12-04United AirlinesUA1856 + UA1222 / UA1952$564.302026-10-29T01:53:24Z
2026-11-27 → 2026-12-04United AirlinesUA1544 + UA1280 / UA1952$564.302026-10-29T01:53:24Z

2026-11-20 · one way · $147.25

  • Frontier Airlines F91901 / F935: ORD 2026-11-20 05:01:00 → SJO 2026-11-20 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
    • F91901: ORD 2026-11-20 05:01:00 → MCO 2026-11-20 08:55:00; layover at MCO: 85 minutes.
    • F935: MCO 2026-11-20 10:20:00 → SJO 2026-11-20 12:41:00.

2026-11-20 · one way · $190.00

  • Avianca AV631 / AV641: ORD 2026-11-20 14:20:00 → SJO 2026-11-20 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
    • AV631: ORD 2026-11-20 14:20:00 → GUA 2026-11-20 18:50:00; layover at GUA: 175 minutes.
    • AV641: GUA 2026-11-20 21:45:00 → SJO 2026-11-20 23:15:00.

2026-11-20 · one way · $232.75

  • American Airlines AA884 / AA310: ORD 2026-11-20 06:05:00 → SJO 2026-11-20 14:35:00; 1 stop(s) via MIA; 510 minutes. Local airport times.
    • AA884: ORD 2026-11-20 06:05:00 → MIA 2026-11-20 10:25:00; layover at MIA: 123 minutes.
    • AA310: MIA 2026-11-20 12:28:00 → SJO 2026-11-20 14:35:00.

2026-11-20 · one way · $237.50

  • United Airlines UA1856 / UA1222: ORD 2026-11-20 10:39:00 → SJO 2026-11-20 19:53:00; 1 stop(s) via EWR; 554 minutes. Local airport times.
    • UA1856: ORD 2026-11-20 10:39:00 → EWR 2026-11-20 13:57:00; layover at EWR: 95 minutes.
    • UA1222: EWR 2026-11-20 15:32:00 → SJO 2026-11-20 19:53:00.

2026-11-20 → 2026-11-23 · $418.00

  • Avianca AV631 / AV641: ORD 2026-11-20 14:20:00 → SJO 2026-11-20 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
    • AV631: ORD 2026-11-20 14:20:00 → GUA 2026-11-20 18:50:00; layover at GUA: 175 minutes.
    • AV641: GUA 2026-11-20 21:45:00 → SJO 2026-11-20 23:15:00.
  • Avianca AV628 / UA2007: SJO 2026-11-23 10:00:00 → ORD 2026-11-23 18:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
    • AV628: SJO 2026-11-23 10:00:00 → GUA 2026-11-23 11:30:00; layover at GUA: 118 minutes.
    • UA2007: GUA 2026-11-23 13:28:00 → ORD 2026-11-23 18:15:00.

2026-11-27 → 2026-12-04 · $461.70

  • Frontier Airlines F91901 / F935: ORD 2026-11-27 05:01:00 → SJO 2026-11-27 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
    • F91901: ORD 2026-11-27 05:01:00 → MCO 2026-11-27 08:55:00; layover at MCO: 85 minutes.
    • F935: MCO 2026-11-27 10:20:00 → SJO 2026-11-27 12:41:00.
  • United Airlines UA1952: SJO 2026-12-04 13:25:00 → ORD 2026-12-04 18:57:00; nonstop; 332 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $512.05

  • American Airlines AA884 / AA310: ORD 2026-11-20 06:05:00 → SJO 2026-11-20 14:35:00; 1 stop(s) via MIA; 510 minutes. Local airport times.
    • AA884: ORD 2026-11-20 06:05:00 → MIA 2026-11-20 10:25:00; layover at MIA: 123 minutes.
    • AA310: MIA 2026-11-20 12:28:00 → SJO 2026-11-20 14:35:00.
  • American Airlines AA318 / AA3320: SJO 2026-11-23 15:54:00 → ORD 2026-11-24 00:53:00; 1 stop(s) via MIA; 539 minutes. Local airport times.
    • AA318: SJO 2026-11-23 15:54:00 → MIA 2026-11-23 20:00:00; layover at MIA: 134 minutes.
    • AA3320: MIA 2026-11-23 22:14:00 → ORD 2026-11-24 00:53:00.

2026-11-20 → 2026-11-23 · $557.65

  • United Airlines UA1544 / UA1280: ORD 2026-11-20 12:40:00 → SJO 2026-11-20 20:39:00; 1 stop(s) via IAH; 479 minutes. Local airport times.
    • UA1544: ORD 2026-11-20 12:40:00 → IAH 2026-11-20 15:41:00; layover at IAH: 76 minutes.
    • UA1280: IAH 2026-11-20 16:57:00 → SJO 2026-11-20 20:39:00.
  • United Airlines UA1952: SJO 2026-11-23 13:25:00 → ORD 2026-11-23 18:57:00; nonstop; 332 minutes. Local airport times.

2026-11-20 · one way · $147.25

  • Frontier Airlines F91596 / F9215: ORD 2026-11-20 05:58:00 → SJO 2026-11-20 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • F91596: ORD 2026-11-20 05:58:00 → ATL 2026-11-20 09:27:00; layover at ATL: 107 minutes.
    • F9215: ATL 2026-11-20 11:14:00 → SJO 2026-11-20 14:16:00.

2026-11-20 · one way · $237.50

  • United Airlines UA1544 / UA1280: ORD 2026-11-20 12:40:00 → SJO 2026-11-20 20:39:00; 1 stop(s) via IAH; 479 minutes. Local airport times.
    • UA1544: ORD 2026-11-20 12:40:00 → IAH 2026-11-20 15:41:00; layover at IAH: 76 minutes.
    • UA1280: IAH 2026-11-20 16:57:00 → SJO 2026-11-20 20:39:00.

2026-11-27 → 2026-12-04 · $428.00

  • Avianca AV631 / AV641: ORD 2026-11-27 14:20:00 → SJO 2026-11-27 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
    • AV631: ORD 2026-11-27 14:20:00 → GUA 2026-11-27 18:50:00; layover at GUA: 175 minutes.
    • AV641: GUA 2026-11-27 21:45:00 → SJO 2026-11-27 23:15:00.
  • Avianca AV628 / UA2007: SJO 2026-12-04 10:00:00 → ORD 2026-12-04 18:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
    • AV628: SJO 2026-12-04 10:00:00 → GUA 2026-12-04 11:30:00; layover at GUA: 118 minutes.
    • UA2007: GUA 2026-12-04 13:28:00 → ORD 2026-12-04 18:15:00.

2026-11-27 → 2026-12-04 · $461.70

  • Frontier Airlines F91596 / F9215: ORD 2026-11-27 05:58:00 → SJO 2026-11-27 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • F91596: ORD 2026-11-27 05:58:00 → ATL 2026-11-27 09:27:00; layover at ATL: 107 minutes.
    • F9215: ATL 2026-11-27 11:14:00 → SJO 2026-11-27 14:16:00.
  • United Airlines UA1952: SJO 2026-12-04 13:25:00 → ORD 2026-12-04 18:57:00; nonstop; 332 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $472.15

  • Frontier Airlines F91901 / F935: ORD 2026-11-20 05:01:00 → SJO 2026-11-20 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
    • F91901: ORD 2026-11-20 05:01:00 → MCO 2026-11-20 08:55:00; layover at MCO: 85 minutes.
    • F935: MCO 2026-11-20 10:20:00 → SJO 2026-11-20 12:41:00.
  • United Airlines UA1952: SJO 2026-11-23 13:25:00 → ORD 2026-11-23 18:57:00; nonstop; 332 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $472.15

  • Frontier Airlines F91596 / F9215: ORD 2026-11-20 05:58:00 → SJO 2026-11-20 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • F91596: ORD 2026-11-20 05:58:00 → ATL 2026-11-20 09:27:00; layover at ATL: 107 minutes.
    • F9215: ATL 2026-11-20 11:14:00 → SJO 2026-11-20 14:16:00.
  • United Airlines UA1952: SJO 2026-11-23 13:25:00 → ORD 2026-11-23 18:57:00; nonstop; 332 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $524.30

  • American Airlines AA884 / AA310: ORD 2026-11-27 06:05:00 → SJO 2026-11-27 14:35:00; 1 stop(s) via MIA; 510 minutes. Local airport times.
    • AA884: ORD 2026-11-27 06:05:00 → MIA 2026-11-27 10:25:00; layover at MIA: 123 minutes.
    • AA310: MIA 2026-11-27 12:28:00 → SJO 2026-11-27 14:35:00.
  • American Airlines AA318 / AA3320: SJO 2026-12-04 15:54:00 → ORD 2026-12-05 00:53:00; 1 stop(s) via MIA; 539 minutes. Local airport times.
    • AA318: SJO 2026-12-04 15:54:00 → MIA 2026-12-04 20:00:00; layover at MIA: 134 minutes.
    • AA3320: MIA 2026-12-04 22:14:00 → ORD 2026-12-05 00:53:00.

2026-11-20 → 2026-11-23 · $557.65

  • United Airlines UA1856 / UA1222: ORD 2026-11-20 10:39:00 → SJO 2026-11-20 19:53:00; 1 stop(s) via EWR; 554 minutes. Local airport times.
    • UA1856: ORD 2026-11-20 10:39:00 → EWR 2026-11-20 13:57:00; layover at EWR: 95 minutes.
    • UA1222: EWR 2026-11-20 15:32:00 → SJO 2026-11-20 19:53:00.
  • United Airlines UA1952: SJO 2026-11-23 13:25:00 → ORD 2026-11-23 18:57:00; nonstop; 332 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $564.30

  • United Airlines UA1856 / UA1222: ORD 2026-11-27 10:39:00 → SJO 2026-11-27 19:53:00; 1 stop(s) via EWR; 554 minutes. Local airport times.
    • UA1856: ORD 2026-11-27 10:39:00 → EWR 2026-11-27 13:57:00; layover at EWR: 95 minutes.
    • UA1222: EWR 2026-11-27 15:32:00 → SJO 2026-11-27 19:53:00.
  • United Airlines UA1952: SJO 2026-12-04 13:25:00 → ORD 2026-12-04 18:57:00; nonstop; 332 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $564.30

  • United Airlines UA1544 / UA1280: ORD 2026-11-27 12:40:00 → SJO 2026-11-27 20:39:00; 1 stop(s) via IAH; 479 minutes. Local airport times.
    • UA1544: ORD 2026-11-27 12:40:00 → IAH 2026-11-27 15:41:00; layover at IAH: 76 minutes.
    • UA1280: IAH 2026-11-27 16:57:00 → SJO 2026-11-27 20:39:00.
  • United Airlines UA1952: SJO 2026-12-04 13:25:00 → ORD 2026-12-04 18:57:00; nonstop; 332 minutes. Local airport times.

More dates for this route