Denver (DEN) to Chicago (MDW), Nov 26–27, 2026: from $338 round trip

Lowest published fare: $338 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 26–27, 2026, 1 adult, economy, checked Oct 29, 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

2026-11-26 → 2026-11-27 · Axel-exclusive $351.00

• Southwest Airlines WN1699: DEN 2026-11-26 14:40:00 → MDW 2026-11-26 17:55:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-26 → 2026-11-27 · Axel-exclusive $351.00

• Southwest Airlines WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-26 → 2026-11-27 · Axel-exclusive $337.50

• Southwest Airlines WN1369 / WN2694: DEN 2026-11-26 11:25:00 → MDW 2026-11-26 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
  • WN1369: DEN 2026-11-26 11:25:00 → MCI 2026-11-26 14:05:00; layover at MCI: 105 minutes.
  • WN2694: MCI 2026-11-26 15:50:00 → MDW 2026-11-26 17:10:00.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-26 → 2026-11-27 · Axel-exclusive $337.50

• Southwest Airlines WN878 / WN878: DEN 2026-11-26 14:25:00 → MDW 2026-11-26 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
  • WN878: DEN 2026-11-26 14:25:00 → CVG 2026-11-26 18:50:00; layover at CVG: 90 minutes.
  • WN878: CVG 2026-11-26 20:20:00 → MDW 2026-11-26 20:30:00.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-26 → 2026-11-27 · Axel-exclusive $337.50

• Southwest Airlines WN1111 / WN537: DEN 2026-11-26 10:45:00 → MDW 2026-11-26 16:55:00; 1 stop(s) via ICT; 310 minutes. Local airport times.
  • WN1111: DEN 2026-11-26 10:45:00 → ICT 2026-11-26 13:05:00; layover at ICT: 120 minutes.
  • WN537: ICT 2026-11-26 15:05:00 → MDW 2026-11-26 16:55:00.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-26 → 2026-11-27 · Axel-exclusive $337.50

• Southwest Airlines WN1756 / WN4933: DEN 2026-11-26 08:35:00 → MDW 2026-11-26 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
  • WN1756: DEN 2026-11-26 08:35:00 → COS 2026-11-26 09:25:00; layover at COS: 75 minutes.
  • WN4933: COS 2026-11-26 10:40:00 → MDW 2026-11-26 14:05:00.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-26 → 2026-11-27 · Axel-exclusive $337.50

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-26 11:05:00 → MDW 2026-11-26 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-26 11:05:00 → MSP 2026-11-26 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-26 15:30:00 → MDW 2026-11-26 17:15:00.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

2026-11-26 → 2026-11-27 · Axel-exclusive $337.50

• Southwest Airlines WN1853 / WN1202: DEN 2026-11-26 11:15:00 → MDW 2026-11-26 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
  • WN1853: DEN 2026-11-26 11:15:00 → TUL 2026-11-26 13:55:00; layover at TUL: 70 minutes.
  • WN1202: TUL 2026-11-26 15:05:00 → MDW 2026-11-26 16:55:00.
• Southwest Airlines WN4606: MDW 2026-11-27 16:25:00 → DEN 2026-11-27 18:10:00; nonstop; 165 minutes. Local airport times.

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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• Nov 27, 2026 · Return options
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For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Nov 26, 2026 · return Nov 27, 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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