Travel with Axel, get the best price.

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

San Juan (SJU) to Chicago (ORD), Nov 27, 2026 – Dec 11, 2026: from $269 round trip

San Juan (SJU) to Chicago (ORD), Nov 27, 2026 – Dec 11, 2026: from $269 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $269 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 27, 2026 – Dec 11, 2026, 1 adult, economy, checked Oct 29, 2026.

SJU → ORD1 adulteconomyRound trip

11 flight options · 5 airlines

Nonstop flights

Fri, Nov 27 – Fri, Dec 11

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

Fri, Nov 27 – Fri, Dec 11

American Airlines
5:00 amSJU
5h 39m
Nonstop
8:39 amORD
American Airlines
8:15 amORD
4h 38m
Nonstop
2:53 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Nov 27 – Fri, Dec 11

United Airlines
8:25 amSJU
5h 22m
Nonstop
11:47 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.

Fri, Nov 27 – Fri, Dec 11

American Airlines
3:52 pmSJU
5h 38m
Nonstop
7:30 pmORD
American Airlines
8:15 amORD
4h 38m
Nonstop
2:53 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Nov 27 – Fri, Dec 11

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

Fri, Nov 27 – Fri, Dec 11

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.

Fri, Nov 27 – Fri, Dec 11

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.

Fri, Nov 27 – Fri, Dec 11

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.

Fri, Nov 27 – Fri, Dec 11

American Airlines
8:30 amSJU
9h 4m
PHL · 2h 15m
3:34 pmORD
American Airlines
8:15 amORD
4h 38m
Nonstop
2:53 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Nov 27 – Fri, Dec 11

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.

Fri, Nov 27 – Fri, Dec 11

United Airlines
8:25 amSJU
5h 24m
Nonstop
11:49 amORD
United Airlines
1:00 pmORD
7h 22m
IAD · 1h 26m
10:22 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Nov 27 – Dec 11, 2026 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Make this trip yours

SJU ⇄ ORD

Economy

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

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Frontier Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

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

Explore this route

All dates for this routeNov 26, 2026 · Return optionsNov 28, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

San Juan (SJU) to Chicago (ORD), Nov 27, 2026 – Dec 11, 2026: from $269 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $269 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 27, 2026 – Dec 11, 2026, 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 datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2026-11-27 → 2026-12-11Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-27 → 2026-12-11American AirlinesAA2436 / AA221305:00:00→08:39:00 5h 39m nonstop · 08:15:00→14:53:00 4h 38m nonstopAxel-exclusive $461.252026-10-29T01:23:44Z
2026-11-27 → 2026-12-11United AirlinesUA2089 / UA199608:25:00→11:47:00 5h 22m nonstop · 08:52:00→15:40:00 4h 48m nonstopAxel-exclusive $472.502026-10-29T01:23:44Z
2026-11-27 → 2026-12-11DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-27 → 2026-12-11Delta Air LinesDL1780 + DL2804 / DL5666 + DL196114:55:00→22:36:00 9h 41m 1 stop via BOS · 06:00:00→16:56:00 8h 56m 1 stop via JFKAxel-exclusive $450.002026-10-29T01:23:44Z
2026-11-27 → 2026-12-11American AirlinesAA2279 / AA221315:52:00→19:30:00 5h 38m nonstop · 08:15:00→14:53:00 4h 38m nonstopAxel-exclusive $461.252026-10-29T01:23:44Z
2026-11-27 → 2026-12-11United AirlinesUA2088 / UA199616:55:00→20:26:00 5h 31m nonstop · 08:52:00→15:40:00 4h 48m nonstopAxel-exclusive $472.502026-10-29T01:23:44Z
2026-11-27 → 2026-12-11Frontier AirlinesF92871 + F91441 / F9334605:19:00→12:00:00 8h 41m 1 stop via ATL · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $268.752026-10-29T01:23:44Z
2026-11-27 → 2026-12-11American AirlinesAA508 + AA595 / AA221308:30:00→15:34:00 9h 04m 1 stop via PHL · 08:15:00→14:53:00 4h 38m nonstopAxel-exclusive $439.382026-10-29T01:23:44Z
2026-11-27 → 2026-12-11United AirlinesUA2022 + UA2331 / UA199608:05:00→14:38:00 8h 33m 1 stop via IAD · 08:52:00→15:40:00 4h 48m nonstopAxel-exclusive $450.632026-10-29T01:23:44Z
2026-11-27 → 2026-12-11United AirlinesUA2089 / UA1128 + UA202508:25:00→11:49:00 5h 24m nonstop · 13:00:00→22:22:00 7h 22m 1 stop via IADAxel-exclusive $455.002026-10-29T01:23:44Z

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.

All hotels in Chicago

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

2026-11-27 → 2026-12-11 · Axel-exclusive $281.25

  • Frontier Airlines F93345: SJU 2026-11-27 19:12:00 → ORD 2026-11-27 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-12-11 23:53:00 → SJU 2026-12-12 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $461.25

  • American Airlines AA2436: SJU 2026-11-27 05:00:00 → ORD 2026-11-27 08:39:00; nonstop; 339 minutes. Local airport times.
  • American Airlines AA2213: ORD 2026-12-11 08:15:00 → SJU 2026-12-11 14:53:00; nonstop; 278 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $472.50

  • United Airlines UA2089: SJU 2026-11-27 08:25:00 → ORD 2026-11-27 11:47:00; nonstop; 322 minutes. Local airport times.
  • United Airlines UA1996: ORD 2026-12-11 08:52:00 → SJU 2026-12-11 15:40:00; nonstop; 288 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $360.00

  • DM DM1003 / DM5420: SJU 2026-11-27 16:24:00 → ORD 2026-11-27 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-27 16:24:00 → PUJ 2026-11-27 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-27 19:10:00 → ORD 2026-11-27 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-12-11 05:45:00 → SJU 2026-12-11 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-12-11 05:45:00 → PUJ 2026-12-11 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-12-11 13:58:00 → SJU 2026-12-11 15:03:00.

2026-11-27 → 2026-12-11 · Axel-exclusive $450.00

  • Delta Air Lines DL1780 / DL2804: SJU 2026-11-27 14:55:00 → ORD 2026-11-27 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
    • DL1780: SJU 2026-11-27 14:55:00 → BOS 2026-11-27 18:11:00; layover at BOS: 149 minutes.
    • DL2804: BOS 2026-11-27 20:40:00 → ORD 2026-11-27 22:36:00.
  • Delta Air Lines DL5666 / DL1961: ORD 2026-12-11 06:00:00 → SJU 2026-12-11 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
    • DL5666: ORD 2026-12-11 06:00:00 → JFK 2026-12-11 09:20:00; layover at JFK: 170 minutes.
    • DL1961: JFK 2026-12-11 12:10:00 → SJU 2026-12-11 16:56:00.

2026-11-27 → 2026-12-11 · Axel-exclusive $461.25

  • American Airlines AA2279: SJU 2026-11-27 15:52:00 → ORD 2026-11-27 19:30:00; nonstop; 338 minutes. Local airport times.
  • American Airlines AA2213: ORD 2026-12-11 08:15:00 → SJU 2026-12-11 14:53:00; nonstop; 278 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $472.50

  • United Airlines UA2088: SJU 2026-11-27 16:55:00 → ORD 2026-11-27 20:26:00; nonstop; 331 minutes. Local airport times.
  • United Airlines UA1996: ORD 2026-12-11 08:52:00 → SJU 2026-12-11 15:40:00; nonstop; 288 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $268.75

  • Frontier Airlines F92871 / F91441: SJU 2026-11-27 05:19:00 → ORD 2026-11-27 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
    • F92871: SJU 2026-11-27 05:19:00 → ATL 2026-11-27 08:26:00; layover at ATL: 131 minutes.
    • F91441: ATL 2026-11-27 10:37:00 → ORD 2026-11-27 12:00:00.
  • Frontier Airlines F93346: ORD 2026-12-11 23:53:00 → SJU 2026-12-12 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $439.38

  • American Airlines AA508 / AA595: SJU 2026-11-27 08:30:00 → ORD 2026-11-27 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
    • AA508: SJU 2026-11-27 08:30:00 → PHL 2026-11-27 11:39:00; layover at PHL: 135 minutes.
    • AA595: PHL 2026-11-27 13:54:00 → ORD 2026-11-27 15:34:00.
  • American Airlines AA2213: ORD 2026-12-11 08:15:00 → SJU 2026-12-11 14:53:00; nonstop; 278 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $450.63

  • United Airlines UA2022 / UA2331: SJU 2026-11-27 08:05:00 → ORD 2026-11-27 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
    • UA2022: SJU 2026-11-27 08:05:00 → IAD 2026-11-27 11:09:00; layover at IAD: 126 minutes.
    • UA2331: IAD 2026-11-27 13:15:00 → ORD 2026-11-27 14:38:00.
  • United Airlines UA1996: ORD 2026-12-11 08:52:00 → SJU 2026-12-11 15:40:00; nonstop; 288 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $455.00

  • United Airlines UA2089: SJU 2026-11-27 08:25:00 → ORD 2026-11-27 11:49:00; nonstop; 324 minutes. Local airport times.
  • United Airlines UA1128 / UA2025: ORD 2026-12-11 13:00:00 → SJU 2026-12-11 22:22:00; 1 stop(s) via IAD; 442 minutes. Local airport times.
    • UA1128: ORD 2026-12-11 13:00:00 → IAD 2026-12-11 16:03:00; layover at IAD: 86 minutes.
    • UA2025: IAD 2026-12-11 17:29:00 → SJU 2026-12-11 22:22:00.

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.

Explore this route

For AI assistants

  • This page: San Juan (SJU) to Chicago (ORD) · Nov 27, 2026 · return Dec 11, 2026: 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.
  • Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
  • 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.