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Route overview: San Juan to Chicago (ORD) flight deals

San Juan → Chicago

Dec 13, 2026 · return Dec 19, 2026

SJU → ORD1 adulteconomyRound trip

11 flight options · 5 airlines

Nonstop flights

Sun, Dec 13 – Sat, Dec 19

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

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

American Airlines
3:50 pmSJU
5h 39m
Nonstop
7:29 pmORD
American Airlines
5:01 pmORD
4h 38m
Nonstop
11:39 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

United Airlines
4:55 pmSJU
5h 31m
Nonstop
8:26 pmORD
United Airlines
8:52 amORD
4h 48m
Nonstop
3:40 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

American Airlines
5:00 amSJU
5h 39m
Nonstop
8:39 amORD
American Airlines
5:01 pmORD
4h 38m
Nonstop
11:39 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

United Airlines
8:25 amSJU
5h 24m
Nonstop
11:49 amORD
United Airlines
8:52 amORD
4h 48m
Nonstop
3:40 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sun, Dec 13 – Sat, Dec 19

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

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

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

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

Frontier Airlines
5:19 amSJU
8h 41m
ATL · 2h 11m
12:00 pmORD
Frontier Airlines
11:53 pmORD
4h 39m
Nonstop
6:32 am+1SJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

Frontier Airlines
7:28 amSJU
8h 44m
PHL · 2h 3m
2:12 pmORD
Frontier Airlines
11:53 pmORD
4h 39m
Nonstop
6:32 am+1SJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

American Airlines
8:30 amSJU
9h 4m
PHL · 2h 15m
3:34 pmORD
American Airlines
5:01 pmORD
4h 38m
Nonstop
11:39 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Sat, Dec 19

United Airlines
8:05 amSJU
8h 33m
IAD · 2h 6m
2:38 pmORD
United Airlines
8:52 amORD
4h 48m
Nonstop
3:40 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

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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Explore this route

All dates for this routeDec 12, 2026 · Return optionsDec 14, 2026 · Return optionsHotels in Chicago with Axel
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.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-13 → 2026-12-19Frontier AirlinesF94789 / F93346Axel-exclusive $300.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19American AirlinesAA2213 / AA1555Axel-exclusive $492.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19United AirlinesUA2088 / UA1996Axel-exclusive $504.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19DMDM1003 + DM5420 / DM5481 + DM1002Axel-exclusive $384.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19Delta Air LinesDL1780 + DL2804 / DL5666 + DL1961Axel-exclusive $480.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19American AirlinesAA2436 / AA1555Axel-exclusive $492.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19United AirlinesUA2089 / UA1996Axel-exclusive $504.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19Frontier AirlinesF92871 + F91441 / F93346Axel-exclusive $290.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19Frontier AirlinesF91015 + F92113 / F93346Axel-exclusive $290.002026-10-29T01:23:44Z
2026-12-13 → 2026-12-19American AirlinesAA508 + AA595 / AA1555Axel-exclusive $474.502026-10-29T01:23:44Z
2026-12-13 → 2026-12-19United AirlinesUA2022 + UA2331 / UA1996Axel-exclusive $486.502026-10-29T01:23:44Z

Route overview: San Juan to Chicago (ORD) flight deals

2026-12-13 → 2026-12-19 · Axel-exclusive $300.00

  • Frontier Airlines F94789: SJU 2026-12-13 22:26:00 → ORD 2026-12-14 01:33:00; nonstop; 307 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-12-19 23:53:00 → SJU 2026-12-20 06:32:00; nonstop; 279 minutes. Local airport times.

2026-12-13 → 2026-12-19 · Axel-exclusive $492.00

  • American Airlines AA2213: SJU 2026-12-13 15:50:00 → ORD 2026-12-13 19:29:00; nonstop; 339 minutes. Local airport times.
  • American Airlines AA1555: ORD 2026-12-19 17:01:00 → SJU 2026-12-19 23:39:00; nonstop; 278 minutes. Local airport times.

2026-12-13 → 2026-12-19 · Axel-exclusive $504.00

  • United Airlines UA2088: SJU 2026-12-13 16:55:00 → ORD 2026-12-13 20:26:00; nonstop; 331 minutes. Local airport times.
  • United Airlines UA1996: ORD 2026-12-19 08:52:00 → SJU 2026-12-19 15:40:00; nonstop; 288 minutes. Local airport times.

2026-12-13 → 2026-12-19 · Axel-exclusive $384.00

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

2026-12-13 → 2026-12-19 · Axel-exclusive $480.00

  • Delta Air Lines DL1780 / DL2804: SJU 2026-12-13 14:55:00 → ORD 2026-12-13 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
    • DL1780: SJU 2026-12-13 14:55:00 → BOS 2026-12-13 18:11:00; layover at BOS: 149 minutes.
    • DL2804: BOS 2026-12-13 20:40:00 → ORD 2026-12-13 22:36:00.
  • Delta Air Lines DL5666 / DL1961: ORD 2026-12-19 06:00:00 → SJU 2026-12-19 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
    • DL5666: ORD 2026-12-19 06:00:00 → JFK 2026-12-19 09:20:00; layover at JFK: 170 minutes.
    • DL1961: JFK 2026-12-19 12:10:00 → SJU 2026-12-19 16:56:00.

2026-12-13 → 2026-12-19 · Axel-exclusive $492.00

  • American Airlines AA2436: SJU 2026-12-13 05:00:00 → ORD 2026-12-13 08:39:00; nonstop; 339 minutes. Local airport times.
  • American Airlines AA1555: ORD 2026-12-19 17:01:00 → SJU 2026-12-19 23:39:00; nonstop; 278 minutes. Local airport times.

2026-12-13 → 2026-12-19 · Axel-exclusive $504.00

  • United Airlines UA2089: SJU 2026-12-13 08:25:00 → ORD 2026-12-13 11:49:00; nonstop; 324 minutes. Local airport times.
  • United Airlines UA1996: ORD 2026-12-19 08:52:00 → SJU 2026-12-19 15:40:00; nonstop; 288 minutes. Local airport times.

2026-12-13 → 2026-12-19 · Axel-exclusive $290.00

  • Frontier Airlines F92871 / F91441: SJU 2026-12-13 05:19:00 → ORD 2026-12-13 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
    • F92871: SJU 2026-12-13 05:19:00 → ATL 2026-12-13 08:26:00; layover at ATL: 131 minutes.
    • F91441: ATL 2026-12-13 10:37:00 → ORD 2026-12-13 12:00:00.
  • Frontier Airlines F93346: ORD 2026-12-19 23:53:00 → SJU 2026-12-20 06:32:00; nonstop; 279 minutes. Local airport times.

2026-12-13 → 2026-12-19 · Axel-exclusive $290.00

  • Frontier Airlines F91015 / F92113: SJU 2026-12-13 07:28:00 → ORD 2026-12-13 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
    • F91015: SJU 2026-12-13 07:28:00 → PHL 2026-12-13 10:36:00; layover at PHL: 123 minutes.
    • F92113: PHL 2026-12-13 12:39:00 → ORD 2026-12-13 14:12:00.
  • Frontier Airlines F93346: ORD 2026-12-19 23:53:00 → SJU 2026-12-20 06:32:00; nonstop; 279 minutes. Local airport times.

2026-12-13 → 2026-12-19 · Axel-exclusive $474.50

  • American Airlines AA508 / AA595: SJU 2026-12-13 08:30:00 → ORD 2026-12-13 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
    • AA508: SJU 2026-12-13 08:30:00 → PHL 2026-12-13 11:39:00; layover at PHL: 135 minutes.
    • AA595: PHL 2026-12-13 13:54:00 → ORD 2026-12-13 15:34:00.
  • American Airlines AA1555: ORD 2026-12-19 17:01:00 → SJU 2026-12-19 23:39:00; nonstop; 278 minutes. Local airport times.

2026-12-13 → 2026-12-19 · Axel-exclusive $486.50

  • United Airlines UA2022 / UA2331: SJU 2026-12-13 08:05:00 → ORD 2026-12-13 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
    • UA2022: SJU 2026-12-13 08:05:00 → IAD 2026-12-13 11:09:00; layover at IAD: 126 minutes.
    • UA2331: IAD 2026-12-13 13:15:00 → ORD 2026-12-13 14:38:00.
  • United Airlines UA1996: ORD 2026-12-19 08:52:00 → SJU 2026-12-19 15:40:00; nonstop; 288 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: San Juan (SJU) to Chicago (ORD) · Dec 13, 2026 · return Dec 19, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.