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

San Juan (SJU) to Chicago (MDW), Nov 7–10, 2026: from $285 round trip

San Juan (SJU) to Chicago (MDW), Nov 7–10, 2026: from $285 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $285 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 7–10, 2026, 1 adult, economy, checked Oct 29, 2026.

SJU → MDW1 adulteconomyRound trip

5 flight options · 2 airlines

One-stop flights

Sat, Nov 7 – Tue, Nov 10

Frontier Airlines
5:01 amSJU
8h 32m
ATL · 2h 5m
11:33 amMDW
Frontier Airlines
1:11 pmMDW
8h 33m
ATL · 2h 48m
11:44 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Tue, Nov 10

Southwest Airlines
2:05 pmSJU
8h 10m
BWI · 2h
8:15 pmMDW
Southwest Airlines
1:20 pmMDW
7h 5m
TPA · 1h 20m
10:25 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Tue, Nov 10

Southwest Airlines
5:35 amSJU
8h 30m
MCO · 2h 25m
12:05 pmMDW
Southwest Airlines
1:20 pmMDW
7h 5m
TPA · 1h 20m
10:25 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Tue, Nov 10

Southwest Airlines
6:05 amSJU
8h 55m
TPA · 2h 55m
1:00 pmMDW
Southwest Airlines
1:20 pmMDW
7h 5m
TPA · 1h 20m
10:25 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Tue, Nov 10

Southwest Airlines
3:30 pmSJU
5h 10m
Nonstop
6:40 pmMDW
Southwest Airlines
1:20 pmMDW
7h 5m
TPA · 1h 20m
10:25 pmSJU

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Nov 7–10, 2026 · 3 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 ⇄ MDW

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 routeNov 8, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

San Juan (SJU) to Chicago (MDW), Nov 7–10, 2026: from $285 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $285 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 7–10, 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)
2026-11-07 → 2026-11-10Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $285.002026-10-29T01:23:44Z
2026-11-07 → 2026-11-10Southwest AirlinesWN4916 + WN1072 / WN3048 + WN336314:05:00→20:15:00 8h 10m 1 stop via BWI · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $395.002026-10-29T01:23:44Z
2026-11-07 → 2026-11-10Southwest AirlinesWN4666 + WN2803 / WN3048 + WN336305:35:00→12:05:00 8h 30m 1 stop via MCO · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $395.002026-10-29T01:23:44Z
2026-11-07 → 2026-11-10Southwest AirlinesWN3957 + WN1854 / WN3048 + WN336306:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $395.002026-10-29T01:23:44Z
2026-11-07 → 2026-11-10Southwest AirlinesWN3881 / WN3048 + WN336315:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $415.002026-10-29T01:23:44Z

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 (MDW) flight deals

2026-11-07 → 2026-11-10 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-11-07 05:01:00 → MDW 2026-11-07 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-07 05:01:00 → ATL 2026-11-07 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-07 10:27:00 → MDW 2026-11-07 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-10 13:11:00 → SJU 2026-11-10 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-10 13:11:00 → ATL 2026-11-10 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-10 19:06:00 → SJU 2026-11-10 23:44:00.

2026-11-07 → 2026-11-10 · Axel-exclusive $395.00

  • Southwest Airlines WN4916 / WN1072: SJU 2026-11-07 14:05:00 → MDW 2026-11-07 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
    • WN4916: SJU 2026-11-07 14:05:00 → BWI 2026-11-07 17:10:00; layover at BWI: 120 minutes.
    • WN1072: BWI 2026-11-07 19:10:00 → MDW 2026-11-07 20:15:00.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-11-10 13:20:00 → SJU 2026-11-10 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-11-10 13:20:00 → TPA 2026-11-10 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-11-10 18:15:00 → SJU 2026-11-10 22:25:00.

2026-11-07 → 2026-11-10 · Axel-exclusive $395.00

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-07 05:35:00 → MDW 2026-11-07 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-07 05:35:00 → MCO 2026-11-07 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-07 10:10:00 → MDW 2026-11-07 12:05:00.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-11-10 13:20:00 → SJU 2026-11-10 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-11-10 13:20:00 → TPA 2026-11-10 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-11-10 18:15:00 → SJU 2026-11-10 22:25:00.

2026-11-07 → 2026-11-10 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-07 06:05:00 → MDW 2026-11-07 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-07 06:05:00 → TPA 2026-11-07 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-07 11:15:00 → MDW 2026-11-07 13:00:00.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-11-10 13:20:00 → SJU 2026-11-10 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-11-10 13:20:00 → TPA 2026-11-10 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-11-10 18:15:00 → SJU 2026-11-10 22:25:00.

2026-11-07 → 2026-11-10 · Axel-exclusive $415.00

  • Southwest Airlines WN3881: SJU 2026-11-07 15:30:00 → MDW 2026-11-07 18:40:00; nonstop; 310 minutes. Local airport times.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-11-10 13:20:00 → SJU 2026-11-10 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-11-10 13:20:00 → TPA 2026-11-10 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-11-10 18:15:00 → SJU 2026-11-10 22:25:00.

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 (MDW) · Nov 7, 2026 · return Nov 10, 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 (MDW) 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.