Denver (DEN) to Chicago (MDW) · Jan 8, 2027 · return Jan 18, 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

2027-01-08 → 2027-01-18 · Axel-exclusive $228.00

• Southwest Airlines WN1853 / WN1202: DEN 2027-01-08 11:15:00 → MDW 2027-01-08 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
  • WN1853: DEN 2027-01-08 11:15:00 → TUL 2027-01-08 13:55:00; layover at TUL: 70 minutes.
  • WN1202: TUL 2027-01-08 15:05:00 → MDW 2027-01-08 16:55:00.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-18 10:05:00 → DEN 2027-01-18 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-18 10:05:00 → OMA 2027-01-18 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-18 13:35:00 → DEN 2027-01-18 14:15:00.

2027-01-08 → 2027-01-18 · Axel-exclusive $228.00

• Southwest Airlines WN2832 / WN3127: DEN 2027-01-08 11:05:00 → MDW 2027-01-08 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
  • WN2832: DEN 2027-01-08 11:05:00 → MSP 2027-01-08 14:05:00; layover at MSP: 85 minutes.
  • WN3127: MSP 2027-01-08 15:30:00 → MDW 2027-01-08 17:15:00.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-18 10:05:00 → DEN 2027-01-18 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-18 10:05:00 → OMA 2027-01-18 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-18 13:35:00 → DEN 2027-01-18 14:15:00.

2027-01-08 → 2027-01-18 · Axel-exclusive $228.00

• Southwest Airlines WN1369 / WN2694: DEN 2027-01-08 11:25:00 → MDW 2027-01-08 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
  • WN1369: DEN 2027-01-08 11:25:00 → MCI 2027-01-08 14:05:00; layover at MCI: 105 minutes.
  • WN2694: MCI 2027-01-08 15:50:00 → MDW 2027-01-08 17:10:00.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-18 10:05:00 → DEN 2027-01-18 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-18 10:05:00 → OMA 2027-01-18 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-18 13:35:00 → DEN 2027-01-18 14:15:00.

2027-01-08 → 2027-01-18 · Axel-exclusive $228.00

• Southwest Airlines WN1111 / WN537: DEN 2027-01-08 10:45:00 → MDW 2027-01-08 16:55:00; 1 stop(s) via ICT; 310 minutes. Local airport times.
  • WN1111: DEN 2027-01-08 10:45:00 → ICT 2027-01-08 13:05:00; layover at ICT: 120 minutes.
  • WN537: ICT 2027-01-08 15:05:00 → MDW 2027-01-08 16:55:00.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-18 10:05:00 → DEN 2027-01-18 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-18 10:05:00 → OMA 2027-01-18 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-18 13:35:00 → DEN 2027-01-18 14:15:00.

2027-01-08 → 2027-01-18 · Axel-exclusive $228.00

• Southwest Airlines WN878 / WN878: DEN 2027-01-08 14:25:00 → MDW 2027-01-08 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
  • WN878: DEN 2027-01-08 14:25:00 → CVG 2027-01-08 18:50:00; layover at CVG: 90 minutes.
  • WN878: CVG 2027-01-08 20:20:00 → MDW 2027-01-08 20:30:00.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-18 10:05:00 → DEN 2027-01-18 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-18 10:05:00 → OMA 2027-01-18 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-18 13:35:00 → DEN 2027-01-18 14:15:00.

2027-01-08 → 2027-01-18 · Axel-exclusive $237.50

• Southwest Airlines WN1697: DEN 2027-01-08 08:55:00 → MDW 2027-01-08 12:15:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-18 10:05:00 → DEN 2027-01-18 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-18 10:05:00 → OMA 2027-01-18 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-18 13:35:00 → DEN 2027-01-18 14:15:00.

Explore this route

• All dates for this route
• Jan 7, 2027 · Return options
• Jan 9, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Jan 8, 2027 · return Jan 18, 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.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Denver to Chicago (MDW) flight deals · Flight search guide.
• 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.

Feedback (optional): Missing info · Axel issue