Denver (DEN) to Chicago (MDW) · Jan 27, 2027 · return Jan 28, 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: Denver to Chicago (MDW) flight deals

2027-01-27 → 2027-01-28 · Axel-exclusive $247.00

• Southwest Airlines WN1697: DEN 2027-01-27 08:45:00 → MDW 2027-01-27 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-27 → 2027-01-28 · Axel-exclusive $247.00

• Southwest Airlines WN1699: DEN 2027-01-27 17:35:00 → MDW 2027-01-27 20:50:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-27 → 2027-01-28 · Axel-exclusive $237.50

• Southwest Airlines WN1756 / WN4933: DEN 2027-01-27 08:35:00 → MDW 2027-01-27 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
  • WN1756: DEN 2027-01-27 08:35:00 → COS 2027-01-27 09:25:00; layover at COS: 75 minutes.
  • WN4933: COS 2027-01-27 10:40:00 → MDW 2027-01-27 14:05:00.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-27 → 2027-01-28 · Axel-exclusive $237.50

• Southwest Airlines WN1853 / WN1202: DEN 2027-01-27 11:15:00 → MDW 2027-01-27 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
  • WN1853: DEN 2027-01-27 11:15:00 → TUL 2027-01-27 13:55:00; layover at TUL: 70 minutes.
  • WN1202: TUL 2027-01-27 15:05:00 → MDW 2027-01-27 16:55:00.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-27 → 2027-01-28 · Axel-exclusive $237.50

• Southwest Airlines WN878 / WN878: DEN 2027-01-27 14:25:00 → MDW 2027-01-27 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
  • WN878: DEN 2027-01-27 14:25:00 → CVG 2027-01-27 18:50:00; layover at CVG: 90 minutes.
  • WN878: CVG 2027-01-27 20:20:00 → MDW 2027-01-27 20:30:00.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-27 → 2027-01-28 · Axel-exclusive $237.50

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-27 11:05:00 → MDW 2027-01-27 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-27 11:05:00 → MSP 2027-01-27 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-27 15:30:00 → MDW 2027-01-27 17:15:00.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-27 → 2027-01-28 · Axel-exclusive $237.50

• Southwest Airlines WN1111 / WN537: DEN 2027-01-27 10:45:00 → MDW 2027-01-27 16:55:00; 1 stop(s) via ICT; 310 minutes. Local airport times.
  • WN1111: DEN 2027-01-27 10:45:00 → ICT 2027-01-27 13:05:00; layover at ICT: 120 minutes.
  • WN537: ICT 2027-01-27 15:05:00 → MDW 2027-01-27 16:55:00.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-27 → 2027-01-28 · Axel-exclusive $237.50

• Southwest Airlines WN1369 / WN2694: DEN 2027-01-27 11:25:00 → MDW 2027-01-27 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
  • WN1369: DEN 2027-01-27 11:25:00 → MCI 2027-01-27 14:05:00; layover at MCI: 105 minutes.
  • WN2694: MCI 2027-01-27 15:50:00 → MDW 2027-01-27 17:10:00.
• Southwest Airlines WN120: MDW 2027-01-28 10:50:00 → DEN 2027-01-28 12:30:00; nonstop; 160 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 26, 2027 · Return options
• Jan 28, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Jan 27, 2027 · return Jan 28, 2027: 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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• 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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