Miami (MIA) to Chicago (MDW) · Jan 17, 2027 · return Jan 31, 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: Miami or Fort Lauderdale to Chicago (MDW) flight deals

2027-01-17 → 2027-01-31 · Axel-exclusive $310.00

• Southwest Airlines WN3082: MIA 2027-01-17 18:25:00 → MDW 2027-01-17 20:45:00; nonstop; 200 minutes. Local airport times.
• Southwest Airlines WN1399: MDW 2027-01-31 12:55:00 → MIA 2027-01-31 16:55:00; nonstop; 180 minutes. Local airport times.

2027-01-17 → 2027-01-31 · Axel-exclusive $345.00

• Delta Air Lines DL3188 / DL1728: MIA 2027-01-17 11:40:00 → MDW 2027-01-17 16:18:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3188: MIA 2027-01-17 11:40:00 → ATL 2027-01-17 13:34:00; layover at ATL: 111 minutes.
  • DL1728: ATL 2027-01-17 15:25:00 → MDW 2027-01-17 16:18:00.
• Delta Air Lines DL4688 / DL2548: MDW 2027-01-31 13:31:00 → MIA 2027-01-31 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
  • DL4688: MDW 2027-01-31 13:31:00 → DTW 2027-01-31 15:44:00; layover at DTW: 150 minutes.
  • DL2548: DTW 2027-01-31 18:14:00 → MIA 2027-01-31 21:16:00.

2027-01-17 → 2027-01-31 · Axel-exclusive $310.00

• Southwest Airlines WN3081: MIA 2027-01-17 06:45:00 → MDW 2027-01-17 08:55:00; nonstop; 190 minutes. Local airport times.
• Southwest Airlines WN1399: MDW 2027-01-31 12:55:00 → MIA 2027-01-31 16:55:00; nonstop; 180 minutes. Local airport times.

2027-01-17 → 2027-01-31 · Axel-exclusive $295.00

• Southwest Airlines WN1425 / WN1070: MIA 2027-01-17 06:30:00 → MDW 2027-01-17 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2027-01-17 06:30:00 → BWI 2027-01-17 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2027-01-17 11:05:00 → MDW 2027-01-17 12:15:00.
• Southwest Airlines WN1399: MDW 2027-01-31 12:55:00 → MIA 2027-01-31 16:55:00; nonstop; 180 minutes. Local airport times.

2027-01-17 → 2027-01-31 · Axel-exclusive $295.00

• Southwest Airlines WN3081: MIA 2027-01-17 06:50:00 → MDW 2027-01-17 09:00:00; nonstop; 190 minutes. Local airport times.
• Southwest Airlines WN3002 / WN301: MDW 2027-01-31 07:40:00 → MIA 2027-01-31 15:05:00; 1 stop(s) via PIT; 385 minutes. Local airport times.
  • WN3002: MDW 2027-01-31 07:40:00 → PIT 2027-01-31 10:00:00; layover at PIT: 145 minutes.
  • WN301: PIT 2027-01-31 12:25:00 → MIA 2027-01-31 15:05:00.

2027-01-17 → 2027-01-31 · Axel-exclusive $295.00

• Southwest Airlines WN3046 / WN3556: MIA 2027-01-17 15:05:00 → MDW 2027-01-17 20:10:00; 1 stop(s) via PIT; 365 minutes. Local airport times.
  • WN3046: MIA 2027-01-17 15:05:00 → PIT 2027-01-17 17:45:00; layover at PIT: 115 minutes.
  • WN3556: PIT 2027-01-17 19:40:00 → MDW 2027-01-17 20:10:00.
• Southwest Airlines WN1399: MDW 2027-01-31 12:55:00 → MIA 2027-01-31 16:55:00; nonstop; 180 minutes. Local airport times.

2027-01-17 → 2027-01-31 · Axel-exclusive $295.00

• Southwest Airlines WN4483 / WN2803: MIA 2027-01-17 06:50:00 → MDW 2027-01-17 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
  • WN4483: MIA 2027-01-17 06:50:00 → MCO 2027-01-17 08:00:00; layover at MCO: 130 minutes.
  • WN2803: MCO 2027-01-17 10:10:00 → MDW 2027-01-17 12:05:00.
• Southwest Airlines WN1399: MDW 2027-01-31 12:55:00 → MIA 2027-01-31 16:55:00; nonstop; 180 minutes. Local airport times.

2027-01-17 → 2027-01-31 · Axel-exclusive $345.00

• Delta Air Lines DL2638 / DL4688: MIA 2027-01-17 08:05:00 → MDW 2027-01-17 13:01:00; 1 stop(s) via DTW; 356 minutes. Local airport times.
  • DL2638: MIA 2027-01-17 08:05:00 → DTW 2027-01-17 11:10:00; layover at DTW: 94 minutes.
  • DL4688: DTW 2027-01-17 12:44:00 → MDW 2027-01-17 13:01:00.
• Delta Air Lines DL4688 / DL2548: MDW 2027-01-31 13:31:00 → MIA 2027-01-31 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
  • DL4688: MDW 2027-01-31 13:31:00 → DTW 2027-01-31 15:44:00; layover at DTW: 150 minutes.
  • DL2548: DTW 2027-01-31 18:14:00 → MIA 2027-01-31 21:16:00.

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
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