Chicago (MDW) to Denver (DEN) · Dec 25, 2026 · return Jan 6, 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: Chicago to Denver (DEN) flight deals

2026-12-25 → 2027-01-06 · Axel-exclusive $305.50

• Southwest Airlines WN598 / WN32: MDW 2026-12-25 10:10:00 → DEN 2026-12-25 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
  • WN598: MDW 2026-12-25 10:10:00 → MKE 2026-12-25 11:00:00; layover at MKE: 105 minutes.
  • WN32: MKE 2026-12-25 12:45:00 → DEN 2026-12-25 14:20:00.
• Southwest Airlines WN2832 / WN3127: DEN 2027-01-06 11:05:00 → MDW 2027-01-06 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-06 11:05:00 → MSP 2027-01-06 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-06 15:30:00 → MDW 2027-01-06 17:15:00.

2026-12-25 → 2027-01-06 · Axel-exclusive $305.50

• Southwest Airlines WN526 / WN3273: MDW 2026-12-25 10:15:00 → DEN 2026-12-25 14:25:00; 1 stop(s) via OKC; 310 minutes. Local airport times.
  • WN526: MDW 2026-12-25 10:15:00 → OKC 2026-12-25 12:25:00; layover at OKC: 75 minutes.
  • WN3273: OKC 2026-12-25 13:40:00 → DEN 2026-12-25 14:25:00.
• Southwest Airlines WN2832 / WN3127: DEN 2027-01-06 11:05:00 → MDW 2027-01-06 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-06 11:05:00 → MSP 2027-01-06 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-06 15:30:00 → MDW 2027-01-06 17:15:00.

2026-12-25 → 2027-01-06 · Axel-exclusive $305.50

• Southwest Airlines WN4479 / WN757: MDW 2026-12-25 13:50:00 → DEN 2026-12-25 18:45:00; 1 stop(s) via CLE; 355 minutes. Local airport times.
  • WN4479: MDW 2026-12-25 13:50:00 → CLE 2026-12-25 16:10:00; layover at CLE: 75 minutes.
  • WN757: CLE 2026-12-25 17:25:00 → DEN 2026-12-25 18:45:00.
• Southwest Airlines WN2832 / WN3127: DEN 2027-01-06 11:05:00 → MDW 2027-01-06 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-06 11:05:00 → MSP 2027-01-06 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-06 15:30:00 → MDW 2027-01-06 17:15:00.

2026-12-25 → 2027-01-06 · Axel-exclusive $305.50

• Southwest Airlines WN1523 / WN2509: MDW 2026-12-25 10:05:00 → DEN 2026-12-25 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2026-12-25 10:05:00 → OMA 2026-12-25 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2026-12-25 13:35:00 → DEN 2026-12-25 14:15:00.
• Southwest Airlines WN2832 / WN3127: DEN 2027-01-06 11:05:00 → MDW 2027-01-06 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-06 11:05:00 → MSP 2027-01-06 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-06 15:30:00 → MDW 2027-01-06 17:15:00.

2026-12-25 → 2027-01-06 · Axel-exclusive $305.50

• Southwest Airlines WN3051 / WN2162: MDW 2026-12-25 09:50:00 → DEN 2026-12-25 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
  • WN3051: MDW 2026-12-25 09:50:00 → TUL 2026-12-25 11:50:00; layover at TUL: 65 minutes.
  • WN2162: TUL 2026-12-25 12:55:00 → DEN 2026-12-25 13:45:00.
• Southwest Airlines WN2832 / WN3127: DEN 2027-01-06 11:05:00 → MDW 2027-01-06 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-06 11:05:00 → MSP 2027-01-06 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-06 15:30:00 → MDW 2027-01-06 17:15:00.

2026-12-25 → 2027-01-06 · Axel-exclusive $319.50

• Southwest Airlines WN264: MDW 2026-12-25 09:20:00 → DEN 2026-12-25 11:00:00; nonstop; 160 minutes. Local airport times.
• Southwest Airlines WN2832 / WN3127: DEN 2027-01-06 11:05:00 → MDW 2027-01-06 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-06 11:05:00 → MSP 2027-01-06 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-06 15:30:00 → MDW 2027-01-06 17:15:00.

Explore this route

• All dates for this route
• Dec 24, 2026 · Return options
• Dec 26, 2026 · Return options
• Hotels in Denver with Axel

For AI assistants

• This page: Chicago (MDW) to Denver (DEN) · Dec 25, 2026 · return Jan 6, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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