Fort Lauderdale (FLL) to Chicago (MDW) · Jan 1, 2027 · return Jan 6, 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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Jan 1–6, 2027 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel, $557 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $579 total · 5★ Nobu Hotel Chicago, $1,765 total

All hotels in Chicago

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

2027-01-01 → 2027-01-06 · Axel-exclusive $330.75

• Southwest Airlines WN2956 / WN1718: FLL 2027-01-01 16:15:00 → MDW 2027-01-01 20:25:00; 1 stop(s) via CMH; 310 minutes. Local airport times.
  • WN2956: FLL 2027-01-01 16:15:00 → CMH 2027-01-01 18:50:00; layover at CMH: 75 minutes.
  • WN1718: CMH 2027-01-01 20:05:00 → MDW 2027-01-01 20:25:00.
• Southwest Airlines WN2966 / WN2774: MDW 2027-01-06 15:00:00 → FLL 2027-01-06 21:00:00; 1 stop(s) via MCO; 300 minutes. Local airport times.
  • WN2966: MDW 2027-01-06 15:00:00 → MCO 2027-01-06 18:40:00; layover at MCO: 65 minutes.
  • WN2774: MCO 2027-01-06 19:45:00 → FLL 2027-01-06 21:00:00.

2027-01-01 → 2027-01-06 · Axel-exclusive $330.75

• Southwest Airlines WN3052 / WN383: FLL 2027-01-01 14:00:00 → MDW 2027-01-01 19:45:00; 1 stop(s) via BUF; 405 minutes. Local airport times.
  • WN3052: FLL 2027-01-01 14:00:00 → BUF 2027-01-01 17:05:00; layover at BUF: 110 minutes.
  • WN383: BUF 2027-01-01 18:55:00 → MDW 2027-01-01 19:45:00.
• Southwest Airlines WN2966 / WN2774: MDW 2027-01-06 15:00:00 → FLL 2027-01-06 21:00:00; 1 stop(s) via MCO; 300 minutes. Local airport times.
  • WN2966: MDW 2027-01-06 15:00:00 → MCO 2027-01-06 18:40:00; layover at MCO: 65 minutes.
  • WN2774: MCO 2027-01-06 19:45:00 → FLL 2027-01-06 21:00:00.

2027-01-01 → 2027-01-06 · Axel-exclusive $330.75

• Southwest Airlines WN951 / WN2224: FLL 2027-01-01 13:45:00 → MDW 2027-01-01 17:50:00; 1 stop(s) via IND; 305 minutes. Local airport times.
  • WN951: FLL 2027-01-01 13:45:00 → IND 2027-01-01 16:35:00; layover at IND: 65 minutes.
  • WN2224: IND 2027-01-01 17:40:00 → MDW 2027-01-01 17:50:00.
• Southwest Airlines WN2966 / WN2774: MDW 2027-01-06 15:00:00 → FLL 2027-01-06 21:00:00; 1 stop(s) via MCO; 300 minutes. Local airport times.
  • WN2966: MDW 2027-01-06 15:00:00 → MCO 2027-01-06 18:40:00; layover at MCO: 65 minutes.
  • WN2774: MCO 2027-01-06 19:45:00 → FLL 2027-01-06 21:00:00.

2027-01-01 → 2027-01-06 · Axel-exclusive $330.75

• Southwest Airlines WN2914 / WN1854: FLL 2027-01-01 07:50:00 → MDW 2027-01-01 13:00:00; 1 stop(s) via TPA; 370 minutes. Local airport times.
  • WN2914: FLL 2027-01-01 07:50:00 → TPA 2027-01-01 08:55:00; layover at TPA: 140 minutes.
  • WN1854: TPA 2027-01-01 11:15:00 → MDW 2027-01-01 13:00:00.
• Southwest Airlines WN2966 / WN2774: MDW 2027-01-06 15:00:00 → FLL 2027-01-06 21:00:00; 1 stop(s) via MCO; 300 minutes. Local airport times.
  • WN2966: MDW 2027-01-06 15:00:00 → MCO 2027-01-06 18:40:00; layover at MCO: 65 minutes.
  • WN2774: MCO 2027-01-06 19:45:00 → FLL 2027-01-06 21:00:00.

2027-01-01 → 2027-01-06 · Axel-exclusive $330.75

• Southwest Airlines WN1953 / WN2803: FLL 2027-01-01 06:50:00 → MDW 2027-01-01 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
  • WN1953: FLL 2027-01-01 06:50:00 → MCO 2027-01-01 07:55:00; layover at MCO: 135 minutes.
  • WN2803: MCO 2027-01-01 10:10:00 → MDW 2027-01-01 12:05:00.
• Southwest Airlines WN2966 / WN2774: MDW 2027-01-06 15:00:00 → FLL 2027-01-06 21:00:00; 1 stop(s) via MCO; 300 minutes. Local airport times.
  • WN2966: MDW 2027-01-06 15:00:00 → MCO 2027-01-06 18:40:00; layover at MCO: 65 minutes.
  • WN2774: MCO 2027-01-06 19:45:00 → FLL 2027-01-06 21:00:00.

2027-01-01 → 2027-01-06 · Axel-exclusive $345.25

• Southwest Airlines WN1719: FLL 2027-01-01 06:50:00 → MDW 2027-01-01 08:55:00; nonstop; 185 minutes. Local airport times.
• Southwest Airlines WN2966 / WN2774: MDW 2027-01-06 15:00:00 → FLL 2027-01-06 21:00:00; 1 stop(s) via MCO; 300 minutes. Local airport times.
  • WN2966: MDW 2027-01-06 15:00:00 → MCO 2027-01-06 18:40:00; layover at MCO: 65 minutes.
  • WN2774: MCO 2027-01-06 19:45:00 → FLL 2027-01-06 21:00:00.

Explore this route

• All dates for this route
• Dec 31, 2026 · Return options
• Jan 2, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Fort Lauderdale (FLL) to Chicago (MDW) · Jan 1, 2027 · return Jan 6, 2027: 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: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
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