San Juan (SJU) to Chicago (MDW), Nov 22, 2026: round trips from $321, one way from $194

San Juan (SJU) to Chicago (MDW), Nov 22, 2026: round trips from $321, one way from $194 on Axel, checked Nov 13, 2026. Lowest published fares: $321 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 22–30, 2026; $194 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 22, 2026; 1 adult, economy, checked Nov 13, 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, labelled with the check date 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 check dates 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 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 22–23, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $105 a night · 4★ Freehand Chicago, $87 a night · 5★ Sofitel Chicago Magnificent Mile, $210 a night
• Hotels in Chicago for these nights (Nov 22–24, 2026 · 2 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $96 a night, $192 for 2 nights · 4★ Freehand Chicago, $86 a night, $172 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $210 a night, $420 for 2 nights
• Hotels in Chicago for these nights (Nov 22–25, 2026 · 3 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $93 a night, $279 for 3 nights · 4★ Freehand Chicago, $81 a night, $244 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $208 a night, $623 for 3 nights
• Hotels in Chicago for these nights (Nov 22–26, 2026 · 4 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $95 a night, $378 for 4 nights · 4★ Freehand Chicago, $79 a night, $315 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $208 a night, $833 for 4 nights
• Hotels in Chicago for these nights (Nov 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $99 a night, $494 for 5 nights · 4★ Freehand Chicago, $80 a night, $399 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $206 a night, $1,032 for 5 nights
• Hotels in Chicago for these nights (Nov 22–28, 2026 · 6 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $112 a night, $671 for 6 nights · 4★ Freehand Chicago, $81 a night, $484 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $223 a night, $1,335 for 6 nights
• Hotels in Chicago for these nights (Nov 22–29, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $121 a night, $847 for 7 nights · 4★ Freehand Chicago, $81 a night, $569 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $233 a night, $1,632 for 7 nights
• Hotels in Chicago for these nights (Nov 22–30, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $124 a night, $989 for 8 nights · 4★ Freehand Chicago, $82 a night, $654 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $243 a night, $1,941 for 8 nights
• Hotels in Chicago for these nights (Nov 22 – Dec 1, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $123 a night, $1,103 for 9 nights · 4★ Freehand Chicago, $82 a night, $738 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $251 a night, $2,258 for 9 nights
• Hotels in Chicago for these nights (Nov 22 – Dec 2, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $124 a night, $1,243 for 10 nights · 4★ Freehand Chicago, $82 a night, $822 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $257 a night, $2,567 for 10 nights
• Hotels in Chicago for these nights (Nov 22 – Dec 3, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $124 a night, $1,362 for 11 nights · 4★ Freehand Chicago, $82 a night, $906 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $260 a night, $2,864 for 11 nights
• Hotels in Chicago for these nights (Nov 22 – Dec 4, 2026 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $123 a night, $1,481 for 12 nights · 4★ Freehand Chicago, $82 a night, $985 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $258 a night, $3,098 for 12 nights
• Hotels in Chicago for these nights (Nov 22 – Dec 5, 2026 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $126 a night, $1,636 for 13 nights · 4★ Freehand Chicago, $82 a night, $1,069 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $261 a night, $3,395 for 13 nights
• Hotels in Chicago for these nights (Nov 22 – Dec 6, 2026 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $129 a night, $1,802 for 14 nights · 4★ Freehand Chicago, $82 a night, $1,152 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $265 a night, $3,704 for 14 nights

All hotels in Chicago

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

2026-11-22 · one way · Axel-exclusive $194

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

2026-11-22 · one way · Axel-exclusive $269

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 20:15:00.

2026-11-22 → 2026-11-23 · Axel-exclusive $356

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

2026-11-22 → 2026-11-23 · Axel-exclusive $494

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-11-23 14:30:00 → SJU 2026-11-24 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-11-23 14:30:00 → BWI 2026-11-23 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-11-23 19:55:00 → SJU 2026-11-24 01:00:00.

2026-11-22 → 2026-11-24 · Axel-exclusive $356

• Frontier Airlines F92871 / F92779: SJU 2026-11-22 05:01:00 → MDW 2026-11-22 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-22 05:01:00 → ATL 2026-11-22 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-22 10:27:00 → MDW 2026-11-22 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-11-24 13:11:00 → SJU 2026-11-24 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-11-24 13:11:00 → ATL 2026-11-24 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-11-24 19:06:00 → SJU 2026-11-24 23:44:00.

2026-11-22 → 2026-11-24 · Axel-exclusive $494

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 20:15:00.
• Southwest Airlines WN3048 / WN3363: MDW 2026-11-24 13:20:00 → SJU 2026-11-24 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2026-11-24 13:20:00 → TPA 2026-11-24 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2026-11-24 18:15:00 → SJU 2026-11-24 22:25:00.

2026-11-22 → 2026-11-25 · Axel-exclusive $356

• Frontier Airlines F92871 / F92779: SJU 2026-11-22 05:01:00 → MDW 2026-11-22 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-22 05:01:00 → ATL 2026-11-22 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-22 10:27:00 → MDW 2026-11-22 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-11-25 13:11:00 → SJU 2026-11-25 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-11-25 13:11:00 → ATL 2026-11-25 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-11-25 19:06:00 → SJU 2026-11-25 23:44:00.

2026-11-22 → 2026-11-25 · Axel-exclusive $494

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

2026-11-22 → 2026-11-26 · Axel-exclusive $356

• Frontier Airlines F92871 / F92779: SJU 2026-11-22 05:01:00 → MDW 2026-11-22 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-22 05:01:00 → ATL 2026-11-22 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-22 10:27:00 → MDW 2026-11-22 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-11-26 13:11:00 → SJU 2026-11-26 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-11-26 13:11:00 → ATL 2026-11-26 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-11-26 19:06:00 → SJU 2026-11-26 23:44:00.

2026-11-22 → 2026-11-26 · Axel-exclusive $494

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-11-26 14:30:00 → SJU 2026-11-27 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-11-26 14:30:00 → BWI 2026-11-26 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-11-26 19:55:00 → SJU 2026-11-27 01:00:00.

2026-11-22 → 2026-11-28 · Axel-exclusive $356

• Frontier Airlines F92871 / F92779: SJU 2026-11-22 05:01:00 → MDW 2026-11-22 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-22 05:01:00 → ATL 2026-11-22 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-22 10:27:00 → MDW 2026-11-22 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-11-28 13:11:00 → SJU 2026-11-28 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-11-28 13:11:00 → ATL 2026-11-28 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-11-28 19:06:00 → SJU 2026-11-28 23:44:00.

2026-11-22 → 2026-11-28 · Axel-exclusive $494

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 20:15:00.
• Southwest Airlines WN3002 / WN4122: MDW 2026-11-28 07:50:00 → SJU 2026-11-28 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
  • WN3002: MDW 2026-11-28 07:50:00 → STL 2026-11-28 09:10:00; layover at STL: 175 minutes.
  • WN4122: STL 2026-11-28 12:05:00 → SJU 2026-11-28 18:25:00.

2026-11-22 → 2026-11-29 · Axel-exclusive $356

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

2026-11-22 → 2026-11-29 · Axel-exclusive $494

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-11-29 14:30:00 → SJU 2026-11-30 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-11-29 14:30:00 → BWI 2026-11-29 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-11-29 19:55:00 → SJU 2026-11-30 01:00:00.

2026-11-22 → 2026-11-30 · Axel-exclusive $321

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

2026-11-22 → 2026-11-30 · Axel-exclusive $444

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 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.

2026-11-22 → 2026-12-02 · Axel-exclusive $321

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

2026-11-22 → 2026-12-02 · Axel-exclusive $444

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 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.

2026-11-22 → 2026-12-03 · Axel-exclusive $321

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

2026-11-22 → 2026-12-03 · Axel-exclusive $444

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 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.

2026-11-22 → 2026-12-04 · Axel-exclusive $321

• Frontier Airlines F92871 / F92779: SJU 2026-11-22 05:01:00 → MDW 2026-11-22 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-11-22 05:01:00 → ATL 2026-11-22 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-11-22 10:27:00 → MDW 2026-11-22 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2026-12-04 13:11:00 → SJU 2026-12-04 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2026-12-04 13:11:00 → ATL 2026-12-04 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2026-12-04 19:06:00 → SJU 2026-12-04 23:44:00.

2026-11-22 → 2026-12-04 · Axel-exclusive $444

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 20:15:00.
• Southwest Airlines WN14 / WN4052: MDW 2026-12-04 14:30:00 → SJU 2026-12-05 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
  • WN14: MDW 2026-12-04 14:30:00 → BWI 2026-12-04 17:15:00; layover at BWI: 160 minutes.
  • WN4052: BWI 2026-12-04 19:55:00 → SJU 2026-12-05 01:00:00.

2026-11-22 → 2026-12-06 · Axel-exclusive $321

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

2026-11-22 → 2026-12-06 · Axel-exclusive $444

• Southwest Airlines WN4916 / WN1072: SJU 2026-11-22 14:05:00 → MDW 2026-11-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-11-22 14:05:00 → BWI 2026-11-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-11-22 19:10:00 → MDW 2026-11-22 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.

Explore this route

• All dates for this route
• Nov 21, 2026 · Return options
• Nov 23, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Juan (SJU) to Chicago (MDW) · Nov 22, 2026 · choose your return date: 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 row is one exact trip for this departure (both dates with the year, the total and its displayed check date); 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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