San Juan (SJU) to Chicago (MDW), Nov 29, 2026: round trips from $321, one way from $194

San Juan (SJU) to Chicago (MDW), Nov 29, 2026: round trips from $321, one way from $194 on Axel, checked Oct 29, 2026. Lowest published fares: $321 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 29–30, 2026; $194 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 29, 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

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 (Nov 29–30, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $101 total · 4★ Warwick Allerton - Chicago, $122 total · 5★ Sofitel Chicago Magnificent Mile, $309 total
• Hotels in Chicago for these nights (Nov 29 – Dec 1, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $188 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $268 total · 5★ Sofitel Chicago Magnificent Mile, $626 total
• Hotels in Chicago for these nights (Nov 29 – Dec 2, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $289 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $402 total · 5★ Sofitel Chicago Magnificent Mile, $935 total
• Hotels in Chicago for these nights (Nov 29 – Dec 3, 2026 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $389 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $537 total · 5★ Sofitel Chicago Magnificent Mile, $1,232 total
• Hotels in Chicago for these nights (Nov 29 – Dec 4, 2026 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel, $495 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $671 total · 5★ Sofitel Chicago Magnificent Mile, $1,466 total
• Hotels in Chicago for these nights (Nov 29 – Dec 5, 2026 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel, $698 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $846 total · 5★ Sofitel Chicago Magnificent Mile, $1,763 total
• Hotels in Chicago for these nights (Nov 29 – Dec 6, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $927 total · 4★ Warwick Allerton - Chicago, $985 total · 5★ Sofitel Chicago Magnificent Mile, $2,072 total
• Hotels in Chicago for these nights (Nov 29 – Dec 7, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,031 total · 4★ Warwick Allerton - Chicago, $1,079 total · 5★ Sofitel Chicago Magnificent Mile, $2,278 total
• Hotels in Chicago for these nights (Nov 29 – Dec 8, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,135 total · 4★ Warwick Allerton - Chicago, $1,164 total · 5★ Sofitel Chicago Magnificent Mile, $2,492 total
• Hotels in Chicago for these nights (Nov 29 – Dec 9, 2026 · 10 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,254 total · 4★ Warwick Allerton - Chicago, $1,253 total · 5★ Waldorf Astoria Chicago, $5,066 total
• Hotels in Chicago for these nights (Nov 29 – Dec 10, 2026 · 11 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,347 total · 4★ Warwick Allerton - Chicago, $1,342 total · 5★ Waldorf Astoria Chicago, $5,518 total
• Hotels in Chicago for these nights (Nov 29 – Dec 11, 2026 · 12 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,441 total · 4★ Warwick Allerton - Chicago, $1,431 total · 5★ Waldorf Astoria Chicago, $6,048 total
• Hotels in Chicago for these nights (Nov 29 – Dec 12, 2026 · 13 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,590 total · 4★ Warwick Allerton - Chicago, $1,559 total · 5★ Waldorf Astoria Chicago, $6,924 total
• Hotels in Chicago for these nights (Nov 29 – Dec 13, 2026 · 14 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,747 total · 4★ Warwick Allerton - Chicago, $1,691 total · 5★ Waldorf Astoria Chicago, $7,948 total

All hotels in Chicago

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

2026-11-29 · one way · Axel-exclusive $193.75

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.

2026-11-29 · one way · Axel-exclusive $268.75

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.

2026-11-29 → 2026-11-30 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-11-30 13:11:00 → SJU 2026-11-30 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-11-30 13:11:00 → ATL 2026-11-30 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-11-30 19:06:00 → SJU 2026-11-30 23:44:00.

2026-11-29 → 2026-11-30 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-11-30 14:30:00 → SJU 2026-12-01 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-11-30 14:30:00 → BWI 2026-11-30 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-11-30 19:55:00 → SJU 2026-12-01 01:00:00.

2026-11-29 → 2026-12-01 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-01 13:11:00 → SJU 2026-12-01 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-01 13:11:00 → ATL 2026-12-01 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-01 19:06:00 → SJU 2026-12-01 23:44:00.

2026-11-29 → 2026-12-01 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN3048 / WN3363: MDW 2026-12-01 13:20:00 → SJU 2026-12-01 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2026-12-01 13:20:00 → TPA 2026-12-01 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2026-12-01 18:15:00 → SJU 2026-12-01 22:25:00.

2026-11-29 → 2026-12-02 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 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.

2026-11-29 → 2026-12-02 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 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.

2026-11-29 → 2026-12-03 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-03 13:11:00 → SJU 2026-12-03 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-03 13:11:00 → ATL 2026-12-03 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-03 19:06:00 → SJU 2026-12-03 23:44:00.

2026-11-29 → 2026-12-03 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-12-03 14:30:00 → SJU 2026-12-04 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-12-03 14:30:00 → BWI 2026-12-03 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-12-03 19:55:00 → SJU 2026-12-04 01:00:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-05 13:11:00 → SJU 2026-12-05 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-05 13:11:00 → ATL 2026-12-05 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-05 19:06:00 → SJU 2026-12-05 23:44:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN3002 / WN4122: MDW 2026-12-05 07:50:00 → SJU 2026-12-05 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
  • WN3002: MDW 2026-12-05 07:50:00 → STL 2026-12-05 09:10:00; layover at STL: 175 minutes.
  • WN4122: STL 2026-12-05 12:05:00 → SJU 2026-12-05 18:25:00.

2026-11-29 → 2026-12-06 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-06 13:11:00 → SJU 2026-12-06 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-06 13:11:00 → ATL 2026-12-06 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-06 19:06:00 → SJU 2026-12-06 23:44:00.

2026-11-29 → 2026-12-06 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-12-06 14:30:00 → SJU 2026-12-07 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-12-06 14:30:00 → BWI 2026-12-06 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-12-06 19:55:00 → SJU 2026-12-07 01:00:00.

2026-11-29 → 2026-12-07 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-07 13:11:00 → SJU 2026-12-07 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-07 13:11:00 → ATL 2026-12-07 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-07 19:06:00 → SJU 2026-12-07 23:44:00.

2026-11-29 → 2026-12-07 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-12-07 14:30:00 → SJU 2026-12-08 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-12-07 14:30:00 → BWI 2026-12-07 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-12-07 19:55:00 → SJU 2026-12-08 01:00:00.

2026-11-29 → 2026-12-09 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-09 13:11:00 → SJU 2026-12-09 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-09 13:11:00 → ATL 2026-12-09 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-09 19:06:00 → SJU 2026-12-09 23:44:00.

2026-11-29 → 2026-12-09 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN3048 / WN3363: MDW 2026-12-09 13:20:00 → SJU 2026-12-09 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2026-12-09 13:20:00 → TPA 2026-12-09 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2026-12-09 18:15:00 → SJU 2026-12-09 22:25:00.

2026-11-29 → 2026-12-10 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-10 13:11:00 → SJU 2026-12-10 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-10 13:11:00 → ATL 2026-12-10 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-10 19:06:00 → SJU 2026-12-10 23:44:00.

2026-11-29 → 2026-12-10 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN3002 / WN4122: MDW 2026-12-10 07:50:00 → SJU 2026-12-10 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
  • WN3002: MDW 2026-12-10 07:50:00 → STL 2026-12-10 09:10:00; layover at STL: 175 minutes.
  • WN4122: STL 2026-12-10 12:05:00 → SJU 2026-12-10 18:25:00.

2026-11-29 → 2026-12-11 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-11 13:11:00 → SJU 2026-12-11 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-11 13:11:00 → ATL 2026-12-11 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-11 19:06:00 → SJU 2026-12-11 23:44:00.

2026-11-29 → 2026-12-11 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN3002 / WN4122: MDW 2026-12-11 07:50:00 → SJU 2026-12-11 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
  • WN3002: MDW 2026-12-11 07:50:00 → STL 2026-12-11 09:10:00; layover at STL: 175 minutes.
  • WN4122: STL 2026-12-11 12:05:00 → SJU 2026-12-11 18:25:00.

2026-11-29 → 2026-12-13 · Axel-exclusive $320.63

• Frontier Airlines F92871 / F92779: SJU 2026-11-29 05:01:00 → MDW 2026-11-29 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-29 05:01:00 → ATL 2026-11-29 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-29 10:27:00 → MDW 2026-11-29 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-13 13:11:00 → SJU 2026-12-13 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-13 13:11:00 → ATL 2026-12-13 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-13 19:06:00 → SJU 2026-12-13 23:44:00.

2026-11-29 → 2026-12-13 · Axel-exclusive $444.38

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-29 14:05:00 → MDW 2026-11-29 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-29 14:05:00 → BWI 2026-11-29 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-29 19:10:00 → MDW 2026-11-29 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-12-13 14:30:00 → SJU 2026-12-14 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-12-13 14:30:00 → BWI 2026-12-13 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-12-13 19:55:00 → SJU 2026-12-14 01:00:00.

Explore this route

• All dates for this route
• Nov 28, 2026 · Return options
• Nov 30, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Juan (SJU) to Chicago (MDW) · Nov 29, 2026 · choose your return date: 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 row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested 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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