Charleston (CHS) to Chicago (MDW) · Jan 25, 2027 · return Jan 30, 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: Charleston to Chicago (MDW) flight deals

2027-01-25 → 2027-01-30 · Axel-exclusive $256.50

• Southwest Airlines WN1178: CHS 2027-01-25 19:00:00 → MDW 2027-01-25 20:20:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN988: MDW 2027-01-30 13:00:00 → CHS 2027-01-30 16:05:00; nonstop; 125 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $313.50

• Delta Air Lines DL5017 / DL4677: CHS 2027-01-25 13:06:00 → MDW 2027-01-25 18:01:00; 1 stop(s) via DTW; 355 minutes. Local airport times.
  • DL5017: CHS 2027-01-25 13:06:00 → DTW 2027-01-25 15:20:00; layover at DTW: 140 minutes.
  • DL4677: DTW 2027-01-25 17:40:00 → MDW 2027-01-25 18:01:00.
• Delta Air Lines DL1063 / DL3179: MDW 2027-01-30 11:28:00 → CHS 2027-01-30 17:54:00; 1 stop(s) via ATL; 326 minutes. Local airport times.
  • DL1063: MDW 2027-01-30 11:28:00 → ATL 2027-01-30 14:22:00; layover at ATL: 140 minutes.
  • DL3179: ATL 2027-01-30 16:42:00 → CHS 2027-01-30 17:54:00.

2027-01-25 → 2027-01-30 · Axel-exclusive $256.50

• Southwest Airlines WN1306: CHS 2027-01-25 06:40:00 → MDW 2027-01-25 07:55:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN988: MDW 2027-01-30 13:00:00 → CHS 2027-01-30 16:05:00; nonstop; 125 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $268.38

• Southwest Airlines WN4375 / WN1070: CHS 2027-01-25 07:20:00 → MDW 2027-01-25 12:15:00; 1 stop(s) via BWI; 355 minutes. Local airport times.
  • WN4375: CHS 2027-01-25 07:20:00 → BWI 2027-01-25 08:50:00; layover at BWI: 135 minutes.
  • WN1070: BWI 2027-01-25 11:05:00 → MDW 2027-01-25 12:15:00.
• Southwest Airlines WN988: MDW 2027-01-30 13:00:00 → CHS 2027-01-30 16:05:00; nonstop; 125 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $268.38

• Southwest Airlines WN1959 / WN2062: CHS 2027-01-25 11:00:00 → MDW 2027-01-25 16:15:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
  • WN1959: CHS 2027-01-25 11:00:00 → BNA 2027-01-25 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2027-01-25 14:45:00 → MDW 2027-01-25 16:15:00.
• Southwest Airlines WN988: MDW 2027-01-30 13:00:00 → CHS 2027-01-30 16:05:00; nonstop; 125 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $313.50

• Delta Air Lines DL1437 / DL1728: CHS 2027-01-25 12:55:00 → MDW 2027-01-25 16:18:00; 1 stop(s) via ATL; 263 minutes. Local airport times.
  • DL1437: CHS 2027-01-25 12:55:00 → ATL 2027-01-25 14:09:00; layover at ATL: 76 minutes.
  • DL1728: ATL 2027-01-25 15:25:00 → MDW 2027-01-25 16:18:00.
• Delta Air Lines DL1063 / DL3179: MDW 2027-01-30 11:28:00 → CHS 2027-01-30 17:54:00; 1 stop(s) via ATL; 326 minutes. Local airport times.
  • DL1063: MDW 2027-01-30 11:28:00 → ATL 2027-01-30 14:22:00; layover at ATL: 140 minutes.
  • DL3179: ATL 2027-01-30 16:42:00 → CHS 2027-01-30 17:54:00.

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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For AI assistants

• This page: Charleston (CHS) to Chicago (MDW) · Jan 25, 2027 · return Jan 30, 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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