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

San Juan → Chicago

Jan 23, 2027 · return Feb 2, 2027

SJU → ORD1 adulteconomyRound trip

11 flight options · 5 airlines

Nonstop flights

Sat, Jan 23 – Tue, Feb 2

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.

Sat, Jan 23 – Tue, Feb 2

American Airlines
5:00 amSJU
5h 39m
Nonstop
8:39 amORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Jan 23 – Tue, Feb 2

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.

Sat, Jan 23 – Tue, Feb 2

American Airlines
3:50 pmSJU
5h 39m
Nonstop
7:29 pmORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Jan 23 – Tue, Feb 2

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.

One-stop flights

Sat, Jan 23 – Tue, Feb 2

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.

Sat, Jan 23 – Tue, Feb 2

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.

Sat, Jan 23 – Tue, Feb 2

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.

Sat, Jan 23 – Tue, Feb 2

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.

Sat, Jan 23 – Tue, Feb 2

American Airlines
8:30 amSJU
9h 4m
PHL · 2h 15m
3:34 pmORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Jan 23 – Tue, Feb 2

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 routeJan 22, 2027 · Return optionsJan 24, 2027 · 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)
2027-01-23 → 2027-02-02Frontier AirlinesF94789 / F93346Axel-exclusive $250.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02American AirlinesAA2436 / AA2571Axel-exclusive $410.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02United AirlinesUA2089 / UA1996Axel-exclusive $420.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02DMDM1003 + DM5420 / DM5481 + DM1002Axel-exclusive $320.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02Delta Air LinesDL1780 + DL2804 / DL5666 + DL1961Axel-exclusive $400.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02American AirlinesAA2213 / AA2571Axel-exclusive $410.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02United AirlinesUA2088 / UA1996Axel-exclusive $420.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02Frontier AirlinesF91015 + F92113 / F93346Axel-exclusive $240.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02Frontier AirlinesF92871 + F91441 / F93346Axel-exclusive $240.002026-10-29T01:23:44Z
2027-01-23 → 2027-02-02American AirlinesAA508 + AA595 / AA2571Axel-exclusive $392.502026-10-29T01:23:44Z
2027-01-23 → 2027-02-02United AirlinesUA2022 + UA2331 / UA1996Axel-exclusive $402.502026-10-29T01:23:44Z

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

2027-01-23 → 2027-02-02 · Axel-exclusive $250.00

  • Frontier Airlines F94789: SJU 2027-01-23 22:26:00 → ORD 2027-01-24 01:33:00; nonstop; 307 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2027-02-02 23:53:00 → SJU 2027-02-03 06:32:00; nonstop; 279 minutes. Local airport times.

2027-01-23 → 2027-02-02 · Axel-exclusive $410.00

  • American Airlines AA2436: SJU 2027-01-23 05:00:00 → ORD 2027-01-23 08:39:00; nonstop; 339 minutes. Local airport times.
  • American Airlines AA2571: ORD 2027-02-02 23:00:00 → SJU 2027-02-03 05:36:00; nonstop; 276 minutes. Local airport times.

2027-01-23 → 2027-02-02 · Axel-exclusive $420.00

  • United Airlines UA2089: SJU 2027-01-23 08:25:00 → ORD 2027-01-23 11:49:00; nonstop; 324 minutes. Local airport times.
  • United Airlines UA1996: ORD 2027-02-02 08:52:00 → SJU 2027-02-02 15:40:00; nonstop; 288 minutes. Local airport times.

2027-01-23 → 2027-02-02 · Axel-exclusive $320.00

  • DM DM1003 / DM5420: SJU 2027-01-23 16:24:00 → ORD 2027-01-23 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2027-01-23 16:24:00 → PUJ 2027-01-23 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2027-01-23 19:10:00 → ORD 2027-01-23 22:20:00.
  • DM DM5481 / DM1002: ORD 2027-02-02 05:45:00 → SJU 2027-02-02 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2027-02-02 05:45:00 → PUJ 2027-02-02 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2027-02-02 13:58:00 → SJU 2027-02-02 15:03:00.

2027-01-23 → 2027-02-02 · Axel-exclusive $400.00

  • Delta Air Lines DL1780 / DL2804: SJU 2027-01-23 14:55:00 → ORD 2027-01-23 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
    • DL1780: SJU 2027-01-23 14:55:00 → BOS 2027-01-23 18:11:00; layover at BOS: 149 minutes.
    • DL2804: BOS 2027-01-23 20:40:00 → ORD 2027-01-23 22:36:00.
  • Delta Air Lines DL5666 / DL1961: ORD 2027-02-02 06:00:00 → SJU 2027-02-02 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
    • DL5666: ORD 2027-02-02 06:00:00 → JFK 2027-02-02 09:20:00; layover at JFK: 170 minutes.
    • DL1961: JFK 2027-02-02 12:10:00 → SJU 2027-02-02 16:56:00.

2027-01-23 → 2027-02-02 · Axel-exclusive $410.00

  • American Airlines AA2213: SJU 2027-01-23 15:50:00 → ORD 2027-01-23 19:29:00; nonstop; 339 minutes. Local airport times.
  • American Airlines AA2571: ORD 2027-02-02 23:00:00 → SJU 2027-02-03 05:36:00; nonstop; 276 minutes. Local airport times.

2027-01-23 → 2027-02-02 · Axel-exclusive $420.00

  • United Airlines UA2088: SJU 2027-01-23 16:55:00 → ORD 2027-01-23 20:26:00; nonstop; 331 minutes. Local airport times.
  • United Airlines UA1996: ORD 2027-02-02 08:52:00 → SJU 2027-02-02 15:40:00; nonstop; 288 minutes. Local airport times.

2027-01-23 → 2027-02-02 · Axel-exclusive $240.00

  • Frontier Airlines F91015 / F92113: SJU 2027-01-23 07:28:00 → ORD 2027-01-23 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
    • F91015: SJU 2027-01-23 07:28:00 → PHL 2027-01-23 10:36:00; layover at PHL: 123 minutes.
    • F92113: PHL 2027-01-23 12:39:00 → ORD 2027-01-23 14:12:00.
  • Frontier Airlines F93346: ORD 2027-02-02 23:53:00 → SJU 2027-02-03 06:32:00; nonstop; 279 minutes. Local airport times.

2027-01-23 → 2027-02-02 · Axel-exclusive $240.00

  • Frontier Airlines F92871 / F91441: SJU 2027-01-23 05:19:00 → ORD 2027-01-23 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
    • F92871: SJU 2027-01-23 05:19:00 → ATL 2027-01-23 08:26:00; layover at ATL: 131 minutes.
    • F91441: ATL 2027-01-23 10:37:00 → ORD 2027-01-23 12:00:00.
  • Frontier Airlines F93346: ORD 2027-02-02 23:53:00 → SJU 2027-02-03 06:32:00; nonstop; 279 minutes. Local airport times.

2027-01-23 → 2027-02-02 · Axel-exclusive $392.50

  • American Airlines AA508 / AA595: SJU 2027-01-23 08:30:00 → ORD 2027-01-23 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
    • AA508: SJU 2027-01-23 08:30:00 → PHL 2027-01-23 11:39:00; layover at PHL: 135 minutes.
    • AA595: PHL 2027-01-23 13:54:00 → ORD 2027-01-23 15:34:00.
  • American Airlines AA2571: ORD 2027-02-02 23:00:00 → SJU 2027-02-03 05:36:00; nonstop; 276 minutes. Local airport times.

2027-01-23 → 2027-02-02 · Axel-exclusive $402.50

  • United Airlines UA2022 / UA2331: SJU 2027-01-23 08:05:00 → ORD 2027-01-23 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
    • UA2022: SJU 2027-01-23 08:05:00 → IAD 2027-01-23 11:09:00; layover at IAD: 126 minutes.
    • UA2331: IAD 2027-01-23 13:15:00 → ORD 2027-01-23 14:38:00.
  • United Airlines UA1996: ORD 2027-02-02 08:52:00 → SJU 2027-02-02 15:40:00; nonstop; 288 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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For AI assistants

  • This page: San Juan (SJU) to Chicago (ORD) · Jan 23, 2027 · return Feb 2, 2027: 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.
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  • 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.