Washington (DCA) to Chicago (MDW) · Nov 6, 2026 · return Nov 9, 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: Washington, DC to Chicago (MDW) flight deals

2026-11-06 → 2026-11-09 · Axel-exclusive $290.00

• Southwest Airlines WN1532: DCA 2026-11-06 06:00:00 → MDW 2026-11-06 07:05:00; nonstop; 125 minutes. Local airport times.
• Southwest Airlines WN3593: MDW 2026-11-09 13:30:00 → DCA 2026-11-09 16:15:00; nonstop; 105 minutes. Local airport times.

2026-11-06 → 2026-11-09 · Axel-exclusive $350.00

• Delta Air Lines DL1558 / DL4688: DCA 2026-11-06 09:45:00 → MDW 2026-11-06 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
  • DL1558: DCA 2026-11-06 09:45:00 → DTW 2026-11-06 11:22:00; layover at DTW: 82 minutes.
  • DL4688: DTW 2026-11-06 12:44:00 → MDW 2026-11-06 13:01:00.
• Delta Air Lines DL4688 / DL2030: MDW 2026-11-09 13:31:00 → DCA 2026-11-09 18:39:00; 1 stop(s) via DTW; 248 minutes. Local airport times.
  • DL4688: MDW 2026-11-09 13:31:00 → DTW 2026-11-09 15:44:00; layover at DTW: 83 minutes.
  • DL2030: DTW 2026-11-09 17:07:00 → DCA 2026-11-09 18:39:00.

2026-11-06 → 2026-11-09 · Axel-exclusive $295.00

• Southwest Airlines WN1532: DCA 2026-11-06 06:10:00 → MDW 2026-11-06 07:15:00; nonstop; 125 minutes. Local airport times.
• Southwest Airlines WN2910 / WN523: MDW 2026-11-09 08:15:00 → DCA 2026-11-09 13:45:00; 1 stop(s) via CMH; 270 minutes. Local airport times.
  • WN2910: MDW 2026-11-09 08:15:00 → CMH 2026-11-09 10:30:00; layover at CMH: 120 minutes.
  • WN523: CMH 2026-11-09 12:30:00 → DCA 2026-11-09 13:45:00.

2026-11-06 → 2026-11-09 · Axel-exclusive $300.00

• Southwest Airlines WN1548 / WN4770: DCA 2026-11-06 18:55:00 → MDW 2026-11-06 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
  • WN1548: DCA 2026-11-06 18:55:00 → STL 2026-11-06 20:25:00; layover at STL: 85 minutes.
  • WN4770: STL 2026-11-06 21:50:00 → MDW 2026-11-06 23:00:00.
• Southwest Airlines WN2910 / WN523: MDW 2026-11-09 08:15:00 → DCA 2026-11-09 13:45:00; 1 stop(s) via CMH; 270 minutes. Local airport times.
  • WN2910: MDW 2026-11-09 08:15:00 → CMH 2026-11-09 10:30:00; layover at CMH: 120 minutes.
  • WN523: CMH 2026-11-09 12:30:00 → DCA 2026-11-09 13:45:00.

2026-11-06 → 2026-11-09 · Axel-exclusive $300.00

• Southwest Airlines WN1515 / WN2062: DCA 2026-11-06 12:35:00 → MDW 2026-11-06 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
  • WN1515: DCA 2026-11-06 12:35:00 → BNA 2026-11-06 13:30:00; layover at BNA: 75 minutes.
  • WN2062: BNA 2026-11-06 14:45:00 → MDW 2026-11-06 16:15:00.
• Southwest Airlines WN2910 / WN523: MDW 2026-11-09 08:15:00 → DCA 2026-11-09 13:45:00; 1 stop(s) via CMH; 270 minutes. Local airport times.
  • WN2910: MDW 2026-11-09 08:15:00 → CMH 2026-11-09 10:30:00; layover at CMH: 120 minutes.
  • WN523: CMH 2026-11-09 12:30:00 → DCA 2026-11-09 13:45:00.

Explore this route

• All dates for this route
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For AI assistants

• This page: Washington (DCA) to Chicago (MDW) · Nov 6, 2026 · return Nov 9, 2026: 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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