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Route overview: Denver to Chicago (MDW) flight deals

Denver → Chicago

Dec 29, 2026 · return Jan 2, 2027

DEN → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Tue, Dec 29 – Sat, Jan 2

Southwest Airlines
2:25 pmDEN
5h 5m
CVG · 1h 30m
8:30 pmMDW
Southwest Airlines
10:10 amMDW
5h 10m
MKE · 1h 45m
2:20 pmDEN

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Sat, Jan 2

Southwest Airlines
11:25 amDEN
4h 45m
MCI · 1h 45m
5:10 pmMDW
Southwest Airlines
10:10 amMDW
5h 10m
MKE · 1h 45m
2:20 pmDEN

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Sat, Jan 2

Southwest Airlines
8:35 amDEN
4h 30m
COS · 1h 15m
2:05 pmMDW
Southwest Airlines
10:10 amMDW
5h 10m
MKE · 1h 45m
2:20 pmDEN

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Sat, Jan 2

Southwest Airlines
11:05 amDEN
5h 10m
MSP · 1h 25m
5:15 pmMDW
Southwest Airlines
10:10 amMDW
5h 10m
MKE · 1h 45m
2:20 pmDEN

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Sat, Jan 2

Southwest Airlines
11:15 amDEN
4h 40m
TUL · 1h 10m
4:55 pmMDW
Southwest Airlines
10:10 amMDW
5h 10m
MKE · 1h 45m
2:20 pmDEN

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Sat, Jan 2

Southwest Airlines
2:05 pmDEN
2h 20m
Nonstop
5:25 pmMDW
Southwest Airlines
10:10 amMDW
5h 10m
MKE · 1h 45m
2:20 pmDEN

Round-trip total · 1 adult · Taxes included

Make this trip yours

DEN ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeDec 28, 2026 → Jan 1, 2027Dec 30, 2026 → Jan 3, 2027
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Denver to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-29 → 2027-01-02Southwest AirlinesWN878 + WN878 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-29 → 2027-01-02Southwest AirlinesWN1369 + WN2694 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-29 → 2027-01-02Southwest AirlinesWN1756 + WN4933 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-29 → 2027-01-02Southwest AirlinesWN2832 + WN3127 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-29 → 2027-01-02Southwest AirlinesWN1853 + WN1202 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-29 → 2027-01-02Southwest AirlinesWN1698 / WN598 + WN32$341.602026-10-29T01:04:33Z

2026-12-29 → 2027-01-02 · $327.60

  • Southwest Airlines WN878 / WN878: DEN 2026-12-29 14:25:00 → MDW 2026-12-29 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
    • WN878: DEN 2026-12-29 14:25:00 → CVG 2026-12-29 18:50:00; layover at CVG: 90 minutes.
    • WN878: CVG 2026-12-29 20:20:00 → MDW 2026-12-29 20:30:00.
  • Southwest Airlines WN598 / WN32: MDW 2027-01-02 10:10:00 → DEN 2027-01-02 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2027-01-02 10:10:00 → MKE 2027-01-02 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2027-01-02 12:45:00 → DEN 2027-01-02 14:20:00.

2026-12-29 → 2027-01-02 · $327.60

  • Southwest Airlines WN1369 / WN2694: DEN 2026-12-29 11:25:00 → MDW 2026-12-29 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
    • WN1369: DEN 2026-12-29 11:25:00 → MCI 2026-12-29 14:05:00; layover at MCI: 105 minutes.
    • WN2694: MCI 2026-12-29 15:50:00 → MDW 2026-12-29 17:10:00.
  • Southwest Airlines WN598 / WN32: MDW 2027-01-02 10:10:00 → DEN 2027-01-02 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2027-01-02 10:10:00 → MKE 2027-01-02 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2027-01-02 12:45:00 → DEN 2027-01-02 14:20:00.

2026-12-29 → 2027-01-02 · $327.60

  • Southwest Airlines WN1756 / WN4933: DEN 2026-12-29 08:35:00 → MDW 2026-12-29 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
    • WN1756: DEN 2026-12-29 08:35:00 → COS 2026-12-29 09:25:00; layover at COS: 75 minutes.
    • WN4933: COS 2026-12-29 10:40:00 → MDW 2026-12-29 14:05:00.
  • Southwest Airlines WN598 / WN32: MDW 2027-01-02 10:10:00 → DEN 2027-01-02 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2027-01-02 10:10:00 → MKE 2027-01-02 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2027-01-02 12:45:00 → DEN 2027-01-02 14:20:00.

2026-12-29 → 2027-01-02 · $327.60

  • Southwest Airlines WN2832 / WN3127: DEN 2026-12-29 11:05:00 → MDW 2026-12-29 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
    • WN2832: DEN 2026-12-29 11:05:00 → MSP 2026-12-29 14:05:00; layover at MSP: 85 minutes.
    • WN3127: MSP 2026-12-29 15:30:00 → MDW 2026-12-29 17:15:00.
  • Southwest Airlines WN598 / WN32: MDW 2027-01-02 10:10:00 → DEN 2027-01-02 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2027-01-02 10:10:00 → MKE 2027-01-02 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2027-01-02 12:45:00 → DEN 2027-01-02 14:20:00.

2026-12-29 → 2027-01-02 · $327.60

  • Southwest Airlines WN1853 / WN1202: DEN 2026-12-29 11:15:00 → MDW 2026-12-29 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
    • WN1853: DEN 2026-12-29 11:15:00 → TUL 2026-12-29 13:55:00; layover at TUL: 70 minutes.
    • WN1202: TUL 2026-12-29 15:05:00 → MDW 2026-12-29 16:55:00.
  • Southwest Airlines WN598 / WN32: MDW 2027-01-02 10:10:00 → DEN 2027-01-02 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2027-01-02 10:10:00 → MKE 2027-01-02 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2027-01-02 12:45:00 → DEN 2027-01-02 14:20:00.

2026-12-29 → 2027-01-02 · $341.60

  • Southwest Airlines WN1698: DEN 2026-12-29 14:05:00 → MDW 2026-12-29 17:25:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN598 / WN32: MDW 2027-01-02 10:10:00 → DEN 2027-01-02 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2027-01-02 10:10:00 → MKE 2027-01-02 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2027-01-02 12:45:00 → DEN 2027-01-02 14:20:00.

Explore this route

For AI assistants

  • This page: Denver (DEN) to Chicago (MDW) · Dec 29, 2026 · return Jan 2, 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.