San Juan (SJU) to Chicago (MDW) · Dec 30, 2026 · return Jan 1, 2027

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.

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

2026-12-30 → 2027-01-01 · Axel-exclusive $399.00

• Frontier Airlines F92871 / F92779: SJU 2026-12-30 05:01:00 → MDW 2026-12-30 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-12-30 05:01:00 → ATL 2026-12-30 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-12-30 10:27:00 → MDW 2026-12-30 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2027-01-01 13:11:00 → SJU 2027-01-01 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2027-01-01 13:11:00 → ATL 2027-01-01 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2027-01-01 19:06:00 → SJU 2027-01-01 23:44:00.

2026-12-30 → 2027-01-01 · Axel-exclusive $553.00

• Southwest Airlines WN4666 / WN2803: SJU 2026-12-30 05:35:00 → MDW 2026-12-30 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
  • WN4666: SJU 2026-12-30 05:35:00 → MCO 2026-12-30 07:45:00; layover at MCO: 145 minutes.
  • WN2803: MCO 2026-12-30 10:10:00 → MDW 2026-12-30 12:05:00.
• Southwest Airlines WN3002 / WN4122: MDW 2027-01-01 07:50:00 → SJU 2027-01-01 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
  • WN3002: MDW 2027-01-01 07:50:00 → STL 2027-01-01 09:10:00; layover at STL: 175 minutes.
  • WN4122: STL 2027-01-01 12:05:00 → SJU 2027-01-01 18:25:00.

2026-12-30 → 2027-01-01 · Axel-exclusive $553.00

• Southwest Airlines WN4916 / WN1072: SJU 2026-12-30 14:05:00 → MDW 2026-12-30 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-12-30 14:05:00 → BWI 2026-12-30 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-12-30 19:10:00 → MDW 2026-12-30 20:15:00.
• Southwest Airlines WN3002 / WN4122: MDW 2027-01-01 07:50:00 → SJU 2027-01-01 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
  • WN3002: MDW 2027-01-01 07:50:00 → STL 2027-01-01 09:10:00; layover at STL: 175 minutes.
  • WN4122: STL 2027-01-01 12:05:00 → SJU 2027-01-01 18:25:00.

2026-12-30 → 2027-01-01 · Axel-exclusive $553.00

• Southwest Airlines WN3957 / WN1854: SJU 2026-12-30 06:05:00 → MDW 2026-12-30 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
  • WN3957: SJU 2026-12-30 06:05:00 → TPA 2026-12-30 08:20:00; layover at TPA: 175 minutes.
  • WN1854: TPA 2026-12-30 11:15:00 → MDW 2026-12-30 13:00:00.
• Southwest Airlines WN3002 / WN4122: MDW 2027-01-01 07:50:00 → SJU 2027-01-01 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
  • WN3002: MDW 2027-01-01 07:50:00 → STL 2027-01-01 09:10:00; layover at STL: 175 minutes.
  • WN4122: STL 2027-01-01 12:05:00 → SJU 2027-01-01 18:25:00.

2026-12-30 → 2027-01-01 · Axel-exclusive $581.00

• Southwest Airlines WN3881: SJU 2026-12-30 15:30:00 → MDW 2026-12-30 18:40:00; nonstop; 310 minutes. Local airport times.
• Southwest Airlines WN3002 / WN4122: MDW 2027-01-01 07:50:00 → SJU 2027-01-01 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
  • WN3002: MDW 2027-01-01 07:50:00 → STL 2027-01-01 09:10:00; layover at STL: 175 minutes.
  • WN4122: STL 2027-01-01 12:05:00 → SJU 2027-01-01 18:25:00.

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

• All dates for this route
• Dec 29, 2026 · Return options
• Dec 31, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Juan (SJU) to Chicago (MDW) · Dec 30, 2026 · return Jan 1, 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.
• 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.

Feedback (optional): Missing info · Axel issue