San Juan (SJU) to Chicago (MDW), Nov 21, 2026 – Dec 2, 2026: from $321 round trip

San Juan (SJU) to Chicago (MDW), Nov 21, 2026 – Dec 2, 2026: from $321 round trip on Axel, checked Nov 15, 2026. Lowest published fare: $321 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 21, 2026 – Dec 2, 2026, 1 adult, economy, checked Nov 15, 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.

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 nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Nov 21 – Dec 2, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $131 a night, $1,441 for 11 nights · 4★ Hotel Lincoln, $149 a night, $1,636 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $256 a night, $2,820.50 for 11 nights

All hotels in Chicago

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

2026-11-21 → 2026-12-02 · Axel-exclusive $321

• Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-02 13:11:00 → SJU 2026-12-02 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-02 13:11:00 → ATL 2026-12-02 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-02 19:06:00 → SJU 2026-12-02 23:44:00.

2026-11-21 → 2026-12-02 · Axel-exclusive $444

• Southwest Airlines WN4666 / WN2803: SJU 2026-11-21 05:35:00 → MDW 2026-11-21 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
  • WN4666: SJU 2026-11-21 05:35:00 → MCO 2026-11-21 07:45:00; layover at MCO: 145 minutes.
  • WN2803: MCO 2026-11-21 10:10:00 → MDW 2026-11-21 12:05:00.
• Southwest Airlines WN3048 / WN3363: MDW 2026-12-02 13:20:00 → SJU 2026-12-02 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2026-12-02 13:20:00 → TPA 2026-12-02 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2026-12-02 18:15:00 → SJU 2026-12-02 22:25:00.

2026-11-21 → 2026-12-02 · Axel-exclusive $444

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-21 14:05:00 → MDW 2026-11-21 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-21 14:05:00 → BWI 2026-11-21 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-21 19:10:00 → MDW 2026-11-21 20:15:00.
• Southwest Airlines WN3048 / WN3363: MDW 2026-12-02 13:20:00 → SJU 2026-12-02 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2026-12-02 13:20:00 → TPA 2026-12-02 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2026-12-02 18:15:00 → SJU 2026-12-02 22:25:00.

2026-11-21 → 2026-12-02 · Axel-exclusive $444

• Southwest Airlines WN3957 / WN1854: SJU 2026-11-21 06:05:00 → MDW 2026-11-21 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
  • WN3957: SJU 2026-11-21 06:05:00 → TPA 2026-11-21 08:20:00; layover at TPA: 175 minutes.
  • WN1854: TPA 2026-11-21 11:15:00 → MDW 2026-11-21 13:00:00.
• Southwest Airlines WN3048 / WN3363: MDW 2026-12-02 13:20:00 → SJU 2026-12-02 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2026-12-02 13:20:00 → TPA 2026-12-02 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2026-12-02 18:15:00 → SJU 2026-12-02 22:25:00.

2026-11-21 → 2026-12-02 · Axel-exclusive $469

• Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
• Southwest Airlines WN3048 / WN3363: MDW 2026-12-02 13:20:00 → SJU 2026-12-02 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2026-12-02 13:20:00 → TPA 2026-12-02 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2026-12-02 18:15:00 → SJU 2026-12-02 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

• All dates for this route
• Nov 20, 2026 · Return options
• Nov 22, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Juan (SJU) to Chicago (MDW) · Nov 21, 2026 · return Dec 2, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. 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 nightly rate and the stay's total, from the lowest saved total 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.

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