Philadelphia (PHL) to Chicago (MDW) · Jan 18, 2027 · return Jan 20, 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: Philadelphia to Chicago (MDW) flight deals

2027-01-18 → 2027-01-20 · Axel-exclusive $266.00

• Southwest Airlines WN2108: PHL 2027-01-18 18:15:00 → MDW 2027-01-18 19:30:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN4363: MDW 2027-01-20 07:35:00 → PHL 2027-01-20 10:25:00; nonstop; 110 minutes. Local airport times.

2027-01-18 → 2027-01-20 · Axel-exclusive $171.00

• Frontier Airlines F91147 / F92291: PHL 2027-01-18 17:14:00 → MDW 2027-01-18 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
  • F91147: PHL 2027-01-18 17:14:00 → ATL 2027-01-18 19:54:00; layover at ATL: 174 minutes.
  • F92291: ATL 2027-01-18 22:48:00 → MDW 2027-01-18 23:47:00.
• Frontier Airlines F92144 / F92552: MDW 2027-01-20 12:28:00 → PHL 2027-01-20 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
  • F92144: MDW 2027-01-20 12:28:00 → ATL 2027-01-20 15:41:00; layover at ATL: 197 minutes.
  • F92552: ATL 2027-01-20 18:58:00 → PHL 2027-01-20 21:07:00.

2027-01-18 → 2027-01-20 · Axel-exclusive $313.50

• Delta Air Lines DL2968 / DL4688: PHL 2027-01-18 09:43:00 → MDW 2027-01-18 13:01:00; 1 stop(s) via DTW; 258 minutes. Local airport times.
  • DL2968: PHL 2027-01-18 09:43:00 → DTW 2027-01-18 11:35:00; layover at DTW: 69 minutes.
  • DL4688: DTW 2027-01-18 12:44:00 → MDW 2027-01-18 13:01:00.
• Delta Air Lines DL4688 / DL1686: MDW 2027-01-20 13:31:00 → PHL 2027-01-20 19:30:00; 1 stop(s) via DTW; 299 minutes. Local airport times.
  • DL4688: MDW 2027-01-20 13:31:00 → DTW 2027-01-20 15:44:00; layover at DTW: 125 minutes.
  • DL1686: DTW 2027-01-20 17:49:00 → PHL 2027-01-20 19:30:00.

2027-01-18 → 2027-01-20 · Axel-exclusive $266.00

• Southwest Airlines WN3372: PHL 2027-01-18 07:30:00 → MDW 2027-01-18 08:50:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4363: MDW 2027-01-20 07:35:00 → PHL 2027-01-20 10:25:00; nonstop; 110 minutes. Local airport times.

2027-01-18 → 2027-01-20 · Axel-exclusive $258.88

• Southwest Airlines WN3375 / WN287: PHL 2027-01-18 06:00:00 → MDW 2027-01-18 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN3375: PHL 2027-01-18 06:00:00 → STL 2027-01-18 07:45:00; layover at STL: 190 minutes.
  • WN287: STL 2027-01-18 10:55:00 → MDW 2027-01-18 12:05:00.
• Southwest Airlines WN4363: MDW 2027-01-20 07:35:00 → PHL 2027-01-20 10:25:00; nonstop; 110 minutes. Local airport times.

2027-01-18 → 2027-01-20 · Axel-exclusive $258.88

• Southwest Airlines WN2080 / WN651: PHL 2027-01-18 14:55:00 → MDW 2027-01-18 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
  • WN2080: PHL 2027-01-18 14:55:00 → BNA 2027-01-18 16:10:00; layover at BNA: 200 minutes.
  • WN651: BNA 2027-01-18 19:30:00 → MDW 2027-01-18 21:05:00.
• Southwest Airlines WN4363: MDW 2027-01-20 07:35:00 → PHL 2027-01-20 10:25:00; nonstop; 110 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 17, 2027 · Return options
• Jan 19, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Philadelphia (PHL) to Chicago (MDW) · Jan 18, 2027 · return Jan 20, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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