Denver (DEN) to Chicago (MDW), Nov 21–30, 2026: from $324 round trip

Denver (DEN) to Chicago (MDW), Nov 21–30, 2026: from $324 round trip on Axel, checked Nov 13, 2026. Lowest published fare: $324 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 21–30, 2026, 1 adult, economy, checked Nov 13, 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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Nov 21–30, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $132 a night, $1,187 for 9 nights · 4★ Freehand Chicago, $82 a night, $739 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $244 a night, $2,194.50 for 9 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2026-11-21 → 2026-11-30 · Axel-exclusive $324

• Southwest Airlines WN1111 / WN537: DEN 2026-11-21 10:45:00 → MDW 2026-11-21 16:55:00; 1 stop(s) via ICT; 310 minutes. Local airport times.
  • WN1111: DEN 2026-11-21 10:45:00 → ICT 2026-11-21 13:05:00; layover at ICT: 120 minutes.
  • WN537: ICT 2026-11-21 15:05:00 → MDW 2026-11-21 16:55:00.
• Southwest Airlines WN3051 / WN2162: MDW 2026-11-30 09:50:00 → DEN 2026-11-30 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-11-30 09:50:00 → TUL 2026-11-30 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-11-30 12:55:00 → DEN 2026-11-30 13:45:00.

2026-11-21 → 2026-11-30 · Axel-exclusive $324

• Southwest Airlines WN878 / WN878: DEN 2026-11-21 14:25:00 → MDW 2026-11-21 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
  • WN878: DEN 2026-11-21 14:25:00 → CVG 2026-11-21 18:50:00; layover at CVG: 90 minutes.
  • WN878: CVG 2026-11-21 20:20:00 → MDW 2026-11-21 20:30:00.
• Southwest Airlines WN3051 / WN2162: MDW 2026-11-30 09:50:00 → DEN 2026-11-30 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-11-30 09:50:00 → TUL 2026-11-30 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-11-30 12:55:00 → DEN 2026-11-30 13:45:00.

2026-11-21 → 2026-11-30 · Axel-exclusive $324

• Southwest Airlines WN2832 / WN3127: DEN 2026-11-21 11:05:00 → MDW 2026-11-21 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2026-11-21 11:05:00 → MSP 2026-11-21 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2026-11-21 15:30:00 → MDW 2026-11-21 17:15:00.
• Southwest Airlines WN3051 / WN2162: MDW 2026-11-30 09:50:00 → DEN 2026-11-30 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-11-30 09:50:00 → TUL 2026-11-30 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-11-30 12:55:00 → DEN 2026-11-30 13:45:00.

2026-11-21 → 2026-11-30 · Axel-exclusive $324

• Southwest Airlines WN1756 / WN4933: DEN 2026-11-21 08:35:00 → MDW 2026-11-21 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
  • WN1756: DEN 2026-11-21 08:35:00 → COS 2026-11-21 09:25:00; layover at COS: 75 minutes.
  • WN4933: COS 2026-11-21 10:40:00 → MDW 2026-11-21 14:05:00.
• Southwest Airlines WN3051 / WN2162: MDW 2026-11-30 09:50:00 → DEN 2026-11-30 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-11-30 09:50:00 → TUL 2026-11-30 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-11-30 12:55:00 → DEN 2026-11-30 13:45:00.

2026-11-21 → 2026-11-30 · Axel-exclusive $324

• Southwest Airlines WN1369 / WN2694: DEN 2026-11-21 11:25:00 → MDW 2026-11-21 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
  • WN1369: DEN 2026-11-21 11:25:00 → MCI 2026-11-21 14:05:00; layover at MCI: 105 minutes.
  • WN2694: MCI 2026-11-21 15:50:00 → MDW 2026-11-21 17:10:00.
• Southwest Airlines WN3051 / WN2162: MDW 2026-11-30 09:50:00 → DEN 2026-11-30 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-11-30 09:50:00 → TUL 2026-11-30 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-11-30 12:55:00 → DEN 2026-11-30 13:45:00.

2026-11-21 → 2026-11-30 · Axel-exclusive $338

• Southwest Airlines WN1699: DEN 2026-11-21 14:50:00 → MDW 2026-11-21 18:05:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN3051 / WN2162: MDW 2026-11-30 09:50:00 → DEN 2026-11-30 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-11-30 09:50:00 → TUL 2026-11-30 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-11-30 12:55:00 → DEN 2026-11-30 13:45:00.

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
• Nov 20, 2026 · Return options
• Nov 22, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Nov 21, 2026 · return Nov 30, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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