San Juan (SJU) to Chicago (ORD), Jan 6–16, 2027: from $280 round trip
San Juan (SJU) to Chicago (ORD), Jan 6–16, 2027: from $280 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $280 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 6–16, 2027, 1 adult, economy, checked Oct 29, 2026. 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 dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2027-01-06 → 2027-01-16 | Frontier Airlines | F94789 / F93346 | 22:26:00→01:33:00 5h 07m nonstop · 23:53:00→06:32:00 4h 39m nonstop | Axel-exclusive $293.75 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | American Airlines | AA2436 / AA1555 | 05:00:00→08:39:00 5h 39m nonstop · 17:01:00→23:39:00 4h 38m nonstop | Axel-exclusive $481.75 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | United Airlines | UA2088 / UA1996 | 16:55:00→20:26:00 5h 31m nonstop · 08:52:00→15:40:00 4h 48m nonstop | Axel-exclusive $493.50 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | DM | DM1003 + DM5420 / DM5481 + DM1002 | 16:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJ | Axel-exclusive $376.00 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | Delta Air Lines | DL1780 + DL2804 / DL5666 + DL1961 | 14:55:00→22:36:00 9h 41m 1 stop via BOS · 06:00:00→16:56:00 8h 56m 1 stop via JFK | Axel-exclusive $470.00 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | American Airlines | AA2213 / AA1555 | 15:50:00→19:29:00 5h 39m nonstop · 17:01:00→23:39:00 4h 38m nonstop | Axel-exclusive $481.75 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | United Airlines | UA2089 / UA1996 | 08:25:00→11:47:00 5h 22m nonstop · 08:52:00→15:40:00 4h 48m nonstop | Axel-exclusive $493.50 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | Frontier Airlines | F91015 + F92113 / F93346 | 07:28:00→14:12:00 8h 44m 1 stop via PHL · 23:53:00→06:32:00 4h 39m nonstop | Axel-exclusive $280.25 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | Frontier Airlines | F92871 + F91441 / F93346 | 05:19:00→12:00:00 8h 41m 1 stop via ATL · 23:53:00→06:32:00 4h 39m nonstop | Axel-exclusive $280.25 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | American Airlines | AA508 + AA595 / AA1555 | 08:30:00→15:34:00 9h 04m 1 stop via PHL · 17:01:00→23:39:00 4h 38m nonstop | Axel-exclusive $458.13 | 2026-10-29T01:23:44Z |
| 2027-01-06 → 2027-01-16 | United Airlines | UA2022 + UA2331 / UA1996 | 08:05:00→14:38:00 8h 33m 1 stop via IAD · 08:52:00→15:40:00 4h 48m nonstop | Axel-exclusive $469.88 | 2026-10-29T01:23:44Z |
Hotels in Chicago for these trips
Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in Chicago for these nights (Jan 6–16, 2027 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Route overview: San Juan to Chicago (ORD) flight deals
2027-01-06 → 2027-01-16 · Axel-exclusive $293.75
- Frontier Airlines F94789: SJU 2027-01-06 22:26:00 → ORD 2027-01-07 01:33:00; nonstop; 307 minutes. Local airport times.
- Frontier Airlines F93346: ORD 2027-01-16 23:53:00 → SJU 2027-01-17 06:32:00; nonstop; 279 minutes. Local airport times.
2027-01-06 → 2027-01-16 · Axel-exclusive $481.75
- American Airlines AA2436: SJU 2027-01-06 05:00:00 → ORD 2027-01-06 08:39:00; nonstop; 339 minutes. Local airport times.
- American Airlines AA1555: ORD 2027-01-16 17:01:00 → SJU 2027-01-16 23:39:00; nonstop; 278 minutes. Local airport times.
2027-01-06 → 2027-01-16 · Axel-exclusive $493.50
- United Airlines UA2088: SJU 2027-01-06 16:55:00 → ORD 2027-01-06 20:26:00; nonstop; 331 minutes. Local airport times.
- United Airlines UA1996: ORD 2027-01-16 08:52:00 → SJU 2027-01-16 15:40:00; nonstop; 288 minutes. Local airport times.
2027-01-06 → 2027-01-16 · Axel-exclusive $376.00
- DM DM1003 / DM5420: SJU 2027-01-06 16:24:00 → ORD 2027-01-06 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
- DM1003: SJU 2027-01-06 16:24:00 → PUJ 2027-01-06 17:25:00; layover at PUJ: 105 minutes.
- DM5420: PUJ 2027-01-06 19:10:00 → ORD 2027-01-06 22:20:00.
- DM DM5481 / DM1002: ORD 2027-01-16 05:45:00 → SJU 2027-01-16 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
- DM5481: ORD 2027-01-16 05:45:00 → PUJ 2027-01-16 12:30:00; layover at PUJ: 88 minutes.
- DM1002: PUJ 2027-01-16 13:58:00 → SJU 2027-01-16 15:03:00.
2027-01-06 → 2027-01-16 · Axel-exclusive $470.00
- Delta Air Lines DL1780 / DL2804: SJU 2027-01-06 14:55:00 → ORD 2027-01-06 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
- DL1780: SJU 2027-01-06 14:55:00 → BOS 2027-01-06 18:11:00; layover at BOS: 149 minutes.
- DL2804: BOS 2027-01-06 20:40:00 → ORD 2027-01-06 22:36:00.
- Delta Air Lines DL5666 / DL1961: ORD 2027-01-16 06:00:00 → SJU 2027-01-16 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
- DL5666: ORD 2027-01-16 06:00:00 → JFK 2027-01-16 09:20:00; layover at JFK: 170 minutes.
- DL1961: JFK 2027-01-16 12:10:00 → SJU 2027-01-16 16:56:00.
2027-01-06 → 2027-01-16 · Axel-exclusive $481.75
- American Airlines AA2213: SJU 2027-01-06 15:50:00 → ORD 2027-01-06 19:29:00; nonstop; 339 minutes. Local airport times.
- American Airlines AA1555: ORD 2027-01-16 17:01:00 → SJU 2027-01-16 23:39:00; nonstop; 278 minutes. Local airport times.
2027-01-06 → 2027-01-16 · Axel-exclusive $493.50
- United Airlines UA2089: SJU 2027-01-06 08:25:00 → ORD 2027-01-06 11:47:00; nonstop; 322 minutes. Local airport times.
- United Airlines UA1996: ORD 2027-01-16 08:52:00 → SJU 2027-01-16 15:40:00; nonstop; 288 minutes. Local airport times.
2027-01-06 → 2027-01-16 · Axel-exclusive $280.25
- Frontier Airlines F91015 / F92113: SJU 2027-01-06 07:28:00 → ORD 2027-01-06 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
- F91015: SJU 2027-01-06 07:28:00 → PHL 2027-01-06 10:36:00; layover at PHL: 123 minutes.
- F92113: PHL 2027-01-06 12:39:00 → ORD 2027-01-06 14:12:00.
- Frontier Airlines F93346: ORD 2027-01-16 23:53:00 → SJU 2027-01-17 06:32:00; nonstop; 279 minutes. Local airport times.
2027-01-06 → 2027-01-16 · Axel-exclusive $280.25
- Frontier Airlines F92871 / F91441: SJU 2027-01-06 05:19:00 → ORD 2027-01-06 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
- F92871: SJU 2027-01-06 05:19:00 → ATL 2027-01-06 08:26:00; layover at ATL: 131 minutes.
- F91441: ATL 2027-01-06 10:37:00 → ORD 2027-01-06 12:00:00.
- Frontier Airlines F93346: ORD 2027-01-16 23:53:00 → SJU 2027-01-17 06:32:00; nonstop; 279 minutes. Local airport times.
2027-01-06 → 2027-01-16 · Axel-exclusive $458.13
- American Airlines AA508 / AA595: SJU 2027-01-06 08:30:00 → ORD 2027-01-06 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
- AA508: SJU 2027-01-06 08:30:00 → PHL 2027-01-06 11:39:00; layover at PHL: 135 minutes.
- AA595: PHL 2027-01-06 13:54:00 → ORD 2027-01-06 15:34:00.
- American Airlines AA1555: ORD 2027-01-16 17:01:00 → SJU 2027-01-16 23:39:00; nonstop; 278 minutes. Local airport times.
2027-01-06 → 2027-01-16 · Axel-exclusive $469.88
- United Airlines UA2022 / UA2331: SJU 2027-01-06 08:05:00 → ORD 2027-01-06 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
- UA2022: SJU 2027-01-06 08:05:00 → IAD 2027-01-06 11:09:00; layover at IAD: 126 minutes.
- UA2331: IAD 2027-01-06 13:15:00 → ORD 2027-01-06 14:38:00.
- United Airlines UA1996: ORD 2027-01-16 08:52:00 → SJU 2027-01-16 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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- Jan 5, 2027 · Return options
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- Hotels in Chicago with Axel
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- This page: San Juan (SJU) to Chicago (ORD) · Jan 6, 2027 · return Jan 16, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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