Miami (MIA) to Chicago (MDW), Dec 18–20, 2026: from $150 one way

Miami (MIA) to Chicago (MDW), Dec 18–20, 2026: from $150 one way on Axel, checked Oct 29, 2026. Lowest published fare: $150 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 18, 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.

Route overview: Miami or Fort Lauderdale to Chicago (MDW) flight deals

2026-12-18 · one way · Axel-exclusive $165.00

• Southwest Airlines WN942: MIA 2026-12-18 12:35:00 → MDW 2026-12-18 14:50:00; nonstop; 195 minutes. Local airport times.

2026-12-18 · one way · Axel-exclusive $185.00

• Delta Air Lines DL3188 / DL1728: MIA 2026-12-18 11:40:00 → MDW 2026-12-18 16:18:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3188: MIA 2026-12-18 11:40:00 → ATL 2026-12-18 13:34:00; layover at ATL: 111 minutes.
  • DL1728: ATL 2026-12-18 15:25:00 → MDW 2026-12-18 16:18:00.

2026-12-19 · one way · Axel-exclusive $231.00

• Southwest Airlines WN2466: MIA 2026-12-19 15:00:00 → MDW 2026-12-19 17:10:00; nonstop; 190 minutes. Local airport times.

2026-12-20 · one way · Axel-exclusive $231.00

• Southwest Airlines WN3082: MIA 2026-12-20 18:25:00 → MDW 2026-12-20 20:45:00; nonstop; 200 minutes. Local airport times.

2026-12-18 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3081: MIA 2026-12-18 06:45:00 → MDW 2026-12-18 08:55:00; nonstop; 190 minutes. Local airport times.

2026-12-19 · one way · Axel-exclusive $231.00

• Southwest Airlines WN3082: MIA 2026-12-19 18:25:00 → MDW 2026-12-19 20:45:00; nonstop; 200 minutes. Local airport times.

2026-12-20 · one way · Axel-exclusive $231.00

• Southwest Airlines WN3081: MIA 2026-12-20 06:45:00 → MDW 2026-12-20 08:55:00; nonstop; 190 minutes. Local airport times.

2026-12-18 · one way · Axel-exclusive $150.00

• Southwest Airlines WN1425 / WN1070: MIA 2026-12-18 06:30:00 → MDW 2026-12-18 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-12-18 06:30:00 → BWI 2026-12-18 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-12-18 11:05:00 → MDW 2026-12-18 12:15:00.

2026-12-18 · one way · Axel-exclusive $150.00

• Southwest Airlines WN1194 / WN1718: MIA 2026-12-18 14:40:00 → MDW 2026-12-18 19:40:00; 1 stop(s) via CMH; 360 minutes. Local airport times.
  • WN1194: MIA 2026-12-18 14:40:00 → CMH 2026-12-18 17:20:00; layover at CMH: 130 minutes.
  • WN1718: CMH 2026-12-18 19:30:00 → MDW 2026-12-18 19:40:00.

2026-12-18 · one way · Axel-exclusive $150.00

• Southwest Airlines WN4483 / WN2803: MIA 2026-12-18 06:50:00 → MDW 2026-12-18 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
  • WN4483: MIA 2026-12-18 06:50:00 → MCO 2026-12-18 08:00:00; layover at MCO: 130 minutes.
  • WN2803: MCO 2026-12-18 10:10:00 → MDW 2026-12-18 12:05:00.

2026-12-18 · one way · Axel-exclusive $150.00

• Southwest Airlines WN3046 / WN3556: MIA 2026-12-18 15:05:00 → MDW 2026-12-18 20:10:00; 1 stop(s) via PIT; 365 minutes. Local airport times.
  • WN3046: MIA 2026-12-18 15:05:00 → PIT 2026-12-18 17:45:00; layover at PIT: 115 minutes.
  • WN3556: PIT 2026-12-18 19:40:00 → MDW 2026-12-18 20:10:00.

2026-12-18 · one way · Axel-exclusive $185.00

• Delta Air Lines DL2638 / DL4688: MIA 2026-12-18 08:05:00 → MDW 2026-12-18 13:01:00; 1 stop(s) via DTW; 356 minutes. Local airport times.
  • DL2638: MIA 2026-12-18 08:05:00 → DTW 2026-12-18 11:10:00; layover at DTW: 94 minutes.
  • DL4688: DTW 2026-12-18 12:44:00 → MDW 2026-12-18 13:01:00.

2026-12-20 · one way · Axel-exclusive $210.00

• Southwest Airlines WN4483 / WN2803: MIA 2026-12-20 06:50:00 → MDW 2026-12-20 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
  • WN4483: MIA 2026-12-20 06:50:00 → MCO 2026-12-20 08:00:00; layover at MCO: 130 minutes.
  • WN2803: MCO 2026-12-20 10:10:00 → MDW 2026-12-20 12:05:00.

2026-12-20 · one way · Axel-exclusive $210.00

• Southwest Airlines WN1194 / WN1718: MIA 2026-12-20 14:40:00 → MDW 2026-12-20 19:40:00; 1 stop(s) via CMH; 360 minutes. Local airport times.
  • WN1194: MIA 2026-12-20 14:40:00 → CMH 2026-12-20 17:20:00; layover at CMH: 130 minutes.
  • WN1718: CMH 2026-12-20 19:30:00 → MDW 2026-12-20 19:40:00.

2026-12-19 · one way · Axel-exclusive $210.00

• Southwest Airlines WN1425 / WN1070: MIA 2026-12-19 06:30:00 → MDW 2026-12-19 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-12-19 06:30:00 → BWI 2026-12-19 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-12-19 11:05:00 → MDW 2026-12-19 12:15:00.

2026-12-20 · one way · Axel-exclusive $210.00

• Southwest Airlines WN3046 / WN3556: MIA 2026-12-20 15:05:00 → MDW 2026-12-20 20:10:00; 1 stop(s) via PIT; 365 minutes. Local airport times.
  • WN3046: MIA 2026-12-20 15:05:00 → PIT 2026-12-20 17:45:00; layover at PIT: 115 minutes.
  • WN3556: PIT 2026-12-20 19:40:00 → MDW 2026-12-20 20:10:00.

2026-12-19 · one way · Axel-exclusive $210.00

• Southwest Airlines WN1194 / WN1718: MIA 2026-12-19 14:40:00 → MDW 2026-12-19 19:40:00; 1 stop(s) via CMH; 360 minutes. Local airport times.
  • WN1194: MIA 2026-12-19 14:40:00 → CMH 2026-12-19 17:20:00; layover at CMH: 130 minutes.
  • WN1718: CMH 2026-12-19 19:30:00 → MDW 2026-12-19 19:40:00.

2026-12-19 · one way · Axel-exclusive $210.00

• Southwest Airlines WN4483 / WN2803: MIA 2026-12-19 06:50:00 → MDW 2026-12-19 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
  • WN4483: MIA 2026-12-19 06:50:00 → MCO 2026-12-19 08:00:00; layover at MCO: 130 minutes.
  • WN2803: MCO 2026-12-19 10:10:00 → MDW 2026-12-19 12:05:00.

2026-12-20 · one way · Axel-exclusive $210.00

• Southwest Airlines WN1425 / WN1070: MIA 2026-12-20 06:30:00 → MDW 2026-12-20 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-12-20 06:30:00 → BWI 2026-12-20 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-12-20 11:05:00 → MDW 2026-12-20 12:15:00.

2026-12-19 · one way · Axel-exclusive $210.00

• Southwest Airlines WN3046 / WN3556: MIA 2026-12-19 15:05:00 → MDW 2026-12-19 20:10:00; 1 stop(s) via PIT; 365 minutes. Local airport times.
  • WN3046: MIA 2026-12-19 15:05:00 → PIT 2026-12-19 17:45:00; layover at PIT: 115 minutes.
  • WN3556: PIT 2026-12-19 19:40:00 → MDW 2026-12-19 20:10:00.

2026-12-20 · one way · Axel-exclusive $259.00

• Delta Air Lines DL3188 / DL1728: MIA 2026-12-20 11:40:00 → MDW 2026-12-20 16:18:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3188: MIA 2026-12-20 11:40:00 → ATL 2026-12-20 13:34:00; layover at ATL: 111 minutes.
  • DL1728: ATL 2026-12-20 15:25:00 → MDW 2026-12-20 16:18:00.

2026-12-19 · one way · Axel-exclusive $259.00

• Delta Air Lines DL2638 / DL4688: MIA 2026-12-19 08:05:00 → MDW 2026-12-19 13:01:00; 1 stop(s) via DTW; 356 minutes. Local airport times.
  • DL2638: MIA 2026-12-19 08:05:00 → DTW 2026-12-19 11:10:00; layover at DTW: 94 minutes.
  • DL4688: DTW 2026-12-19 12:44:00 → MDW 2026-12-19 13:01:00.

2026-12-20 · one way · Axel-exclusive $259.00

• Delta Air Lines DL2638 / DL4688: MIA 2026-12-20 08:05:00 → MDW 2026-12-20 13:01:00; 1 stop(s) via DTW; 356 minutes. Local airport times.
  • DL2638: MIA 2026-12-20 08:05:00 → DTW 2026-12-20 11:10:00; layover at DTW: 94 minutes.
  • DL4688: DTW 2026-12-20 12:44:00 → MDW 2026-12-20 13:01:00.

2026-12-19 · one way · Axel-exclusive $259.00

• Delta Air Lines DL3188 / DL1728: MIA 2026-12-19 11:40:00 → MDW 2026-12-19 16:18:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3188: MIA 2026-12-19 11:40:00 → ATL 2026-12-19 13:34:00; layover at ATL: 111 minutes.
  • DL1728: ATL 2026-12-19 15:25:00 → MDW 2026-12-19 16:18:00.

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.

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