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

San Juan → Chicago

Dec 21, 2026 · one way

SJU → ORD1 adulteconomyOne way

11 flight options · 5 airlines

Nonstop flights

Mon, Dec 21 · One way

Frontier Airlines
7:12 pmSJU
5h 9m
Nonstop
10:21 pmORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

American Airlines
3:50 pmSJU
5h 39m
Nonstop
7:29 pmORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

United Airlines
8:25 amSJU
5h 24m
Nonstop
11:49 amORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

American Airlines
5:00 amSJU
5h 39m
Nonstop
8:39 amORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

United Airlines
4:55 pmSJU
5h 31m
Nonstop
8:26 pmORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Mon, Dec 21 · One way

DM
4:24 pmSJU
7h 56m
PUJ · 1h 45m
10:20 pmORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

Delta Air Lines
2:55 pmSJU
9h 41m
BOS · 2h 29m
10:36 pmORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

Frontier Airlines
5:19 amSJU
8h 41m
ATL · 2h 11m
12:00 pmORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

Frontier Airlines
7:28 amSJU
8h 44m
PHL · 2h 3m
2:12 pmORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

American Airlines
8:30 amSJU
9h 4m
PHL · 2h 15m
3:34 pmORD

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Dec 21 · One way

United Airlines
8:05 amSJU
8h 33m
IAD · 2h 6m
2:38 pmORD

One-way 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 20, 2026 · Return optionsDec 22, 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)
2026-12-21 · one wayFrontier AirlinesF93345Axel-exclusive $182.002026-10-29T01:23:44Z
2026-12-21 · one wayAmerican AirlinesAA2213Axel-exclusive $301.002026-10-29T01:23:44Z
2026-12-21 · one wayUnited AirlinesUA2089Axel-exclusive $308.002026-10-29T01:23:44Z
2026-12-21 · one wayDMDM1003 + DM5420Axel-exclusive $231.002026-10-29T01:23:44Z
2026-12-21 · one wayDelta Air LinesDL1780 + DL2804Axel-exclusive $294.002026-10-29T01:23:44Z
2026-12-21 · one wayAmerican AirlinesAA2436Axel-exclusive $301.002026-10-29T01:23:44Z
2026-12-21 · one wayUnited AirlinesUA2088Axel-exclusive $308.002026-10-29T01:23:44Z
2026-12-21 · one wayFrontier AirlinesF92871 + F91441Axel-exclusive $168.002026-10-29T01:23:44Z
2026-12-21 · one wayFrontier AirlinesF91015 + F92113Axel-exclusive $168.002026-10-29T01:23:44Z
2026-12-21 · one wayAmerican AirlinesAA508 + AA595Axel-exclusive $273.002026-10-29T01:23:44Z
2026-12-21 · one wayUnited AirlinesUA2022 + UA2331Axel-exclusive $280.002026-10-29T01:23:44Z

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

2026-12-21 · one way · Axel-exclusive $182.00

  • Frontier Airlines F93345: SJU 2026-12-21 19:12:00 → ORD 2026-12-21 22:21:00; nonstop; 309 minutes. Local airport times.

2026-12-21 · one way · Axel-exclusive $301.00

  • American Airlines AA2213: SJU 2026-12-21 15:50:00 → ORD 2026-12-21 19:29:00; nonstop; 339 minutes. Local airport times.

2026-12-21 · one way · Axel-exclusive $308.00

  • United Airlines UA2089: SJU 2026-12-21 08:25:00 → ORD 2026-12-21 11:49:00; nonstop; 324 minutes. Local airport times.

2026-12-21 · one way · Axel-exclusive $231.00

  • DM DM1003 / DM5420: SJU 2026-12-21 16:24:00 → ORD 2026-12-21 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-12-21 16:24:00 → PUJ 2026-12-21 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-12-21 19:10:00 → ORD 2026-12-21 22:20:00.

2026-12-21 · one way · Axel-exclusive $294.00

  • Delta Air Lines DL1780 / DL2804: SJU 2026-12-21 14:55:00 → ORD 2026-12-21 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
    • DL1780: SJU 2026-12-21 14:55:00 → BOS 2026-12-21 18:11:00; layover at BOS: 149 minutes.
    • DL2804: BOS 2026-12-21 20:40:00 → ORD 2026-12-21 22:36:00.

2026-12-21 · one way · Axel-exclusive $301.00

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

2026-12-21 · one way · Axel-exclusive $308.00

  • United Airlines UA2088: SJU 2026-12-21 16:55:00 → ORD 2026-12-21 20:26:00; nonstop; 331 minutes. Local airport times.

2026-12-21 · one way · Axel-exclusive $168.00

  • Frontier Airlines F92871 / F91441: SJU 2026-12-21 05:19:00 → ORD 2026-12-21 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
    • F92871: SJU 2026-12-21 05:19:00 → ATL 2026-12-21 08:26:00; layover at ATL: 131 minutes.
    • F91441: ATL 2026-12-21 10:37:00 → ORD 2026-12-21 12:00:00.

2026-12-21 · one way · Axel-exclusive $168.00

  • Frontier Airlines F91015 / F92113: SJU 2026-12-21 07:28:00 → ORD 2026-12-21 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
    • F91015: SJU 2026-12-21 07:28:00 → PHL 2026-12-21 10:36:00; layover at PHL: 123 minutes.
    • F92113: PHL 2026-12-21 12:39:00 → ORD 2026-12-21 14:12:00.

2026-12-21 · one way · Axel-exclusive $273.00

  • American Airlines AA508 / AA595: SJU 2026-12-21 08:30:00 → ORD 2026-12-21 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
    • AA508: SJU 2026-12-21 08:30:00 → PHL 2026-12-21 11:39:00; layover at PHL: 135 minutes.
    • AA595: PHL 2026-12-21 13:54:00 → ORD 2026-12-21 15:34:00.

2026-12-21 · one way · Axel-exclusive $280.00

  • United Airlines UA2022 / UA2331: SJU 2026-12-21 08:05:00 → ORD 2026-12-21 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
    • UA2022: SJU 2026-12-21 08:05:00 → IAD 2026-12-21 11:09:00; layover at IAD: 126 minutes.
    • UA2331: IAD 2026-12-21 13:15:00 → ORD 2026-12-21 14:38:00.

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For AI assistants

  • This page: San Juan (SJU) to Chicago (ORD) · Dec 21, 2026 · one way: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Juan to Chicago (ORD) flight deals · Flight search guide.
  • 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.