Denver (DEN) to Chicago (MDW) · Nov 30, 2026 · return Dec 14, 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: Denver to Chicago (MDW) flight deals

2026-11-30 → 2026-12-14 · Axel-exclusive $282.00

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-30 11:05:00 → MDW 2026-11-30 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-30 11:05:00 → MSP 2026-11-30 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-30 15:30:00 → MDW 2026-11-30 17:15:00.
• Southwest Airlines WN1523 / WN2509: MDW 2026-12-14 10:05:00 → DEN 2026-12-14 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2026-12-14 10:05:00 → OMA 2026-12-14 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2026-12-14 13:35:00 → DEN 2026-12-14 14:15:00.

2026-11-30 → 2026-12-14 · Axel-exclusive $282.00

• Southwest Airlines WN1756 / WN4933: DEN 2026-11-30 08:35:00 → MDW 2026-11-30 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
  • WN1756: DEN 2026-11-30 08:35:00 → COS 2026-11-30 09:25:00; layover at COS: 75 minutes.
  • WN4933: COS 2026-11-30 10:40:00 → MDW 2026-11-30 14:05:00.
• Southwest Airlines WN1523 / WN2509: MDW 2026-12-14 10:05:00 → DEN 2026-12-14 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2026-12-14 10:05:00 → OMA 2026-12-14 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2026-12-14 13:35:00 → DEN 2026-12-14 14:15:00.

2026-11-30 → 2026-12-14 · Axel-exclusive $282.00

• Southwest Airlines WN1853 / WN1202: DEN 2026-11-30 11:15:00 → MDW 2026-11-30 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
  • WN1853: DEN 2026-11-30 11:15:00 → TUL 2026-11-30 13:55:00; layover at TUL: 70 minutes.
  • WN1202: TUL 2026-11-30 15:05:00 → MDW 2026-11-30 16:55:00.
• Southwest Airlines WN1523 / WN2509: MDW 2026-12-14 10:05:00 → DEN 2026-12-14 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2026-12-14 10:05:00 → OMA 2026-12-14 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2026-12-14 13:35:00 → DEN 2026-12-14 14:15:00.

2026-11-30 → 2026-12-14 · Axel-exclusive $282.00

• Southwest Airlines WN1369 / WN2694: DEN 2026-11-30 11:25:00 → MDW 2026-11-30 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
  • WN1369: DEN 2026-11-30 11:25:00 → MCI 2026-11-30 14:05:00; layover at MCI: 105 minutes.
  • WN2694: MCI 2026-11-30 15:50:00 → MDW 2026-11-30 17:10:00.
• Southwest Airlines WN1523 / WN2509: MDW 2026-12-14 10:05:00 → DEN 2026-12-14 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2026-12-14 10:05:00 → OMA 2026-12-14 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2026-12-14 13:35:00 → DEN 2026-12-14 14:15:00.

2026-11-30 → 2026-12-14 · Axel-exclusive $282.00

• Southwest Airlines WN878 / WN878: DEN 2026-11-30 14:25:00 → MDW 2026-11-30 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
  • WN878: DEN 2026-11-30 14:25:00 → CVG 2026-11-30 18:50:00; layover at CVG: 90 minutes.
  • WN878: CVG 2026-11-30 20:20:00 → MDW 2026-11-30 20:30:00.
• Southwest Airlines WN1523 / WN2509: MDW 2026-12-14 10:05:00 → DEN 2026-12-14 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2026-12-14 10:05:00 → OMA 2026-12-14 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2026-12-14 13:35:00 → DEN 2026-12-14 14:15:00.

2026-11-30 → 2026-12-14 · Axel-exclusive $295.50

• Southwest Airlines WN1699: DEN 2026-11-30 14:40:00 → MDW 2026-11-30 17:55:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN1523 / WN2509: MDW 2026-12-14 10:05:00 → DEN 2026-12-14 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2026-12-14 10:05:00 → OMA 2026-12-14 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2026-12-14 13:35:00 → DEN 2026-12-14 14:15:00.

Explore this route

• All dates for this route
• Nov 29, 2026 · Return options
• Dec 1, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Nov 30, 2026 · return Dec 14, 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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