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Route overview: Denver to Chicago (MDW) flight deals

Denver → Chicago

Dec 19, 2026 · return Jan 2, 2027

DEN → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Sat, Dec 19 – 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

Sat, Dec 19 – 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

Sat, Dec 19 – Sat, Jan 2

Southwest Airlines
10:45 amDEN
5h 10m
ICT · 2h
4:55 pmMDW
Southwest Airlines
10:10 amMDW
5h 10m
MKE · 1h 45m
2:20 pmDEN

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – 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

Sat, Dec 19 – 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

Sat, Dec 19 – Sat, Jan 2

Southwest Airlines
2:50 pmDEN
2h 15m
Nonstop
6:05 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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All dates for this routeDec 18, 2026 → Jan 1, 2027Dec 20, 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.

Route overview: Denver to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-19 → 2027-01-02Southwest AirlinesWN1756 + WN4933 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-19 → 2027-01-02Southwest AirlinesWN1369 + WN2694 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-19 → 2027-01-02Southwest AirlinesWN1111 + WN537 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-19 → 2027-01-02Southwest AirlinesWN878 + WN878 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-19 → 2027-01-02Southwest AirlinesWN1853 + WN1202 / WN598 + WN32$327.602026-10-29T01:04:33Z
2026-12-19 → 2027-01-02Southwest AirlinesWN1699 / WN598 + WN32$341.602026-10-29T01:04:33Z

2026-12-19 → 2027-01-02 · $327.60

  • Southwest Airlines WN1756 / WN4933: DEN 2026-12-19 08:35:00 → MDW 2026-12-19 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
    • WN1756: DEN 2026-12-19 08:35:00 → COS 2026-12-19 09:25:00; layover at COS: 75 minutes.
    • WN4933: COS 2026-12-19 10:40:00 → MDW 2026-12-19 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.

2026-12-19 → 2027-01-02 · $327.60

  • Southwest Airlines WN1369 / WN2694: DEN 2026-12-19 11:25:00 → MDW 2026-12-19 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
    • WN1369: DEN 2026-12-19 11:25:00 → MCI 2026-12-19 14:05:00; layover at MCI: 105 minutes.
    • WN2694: MCI 2026-12-19 15:50:00 → MDW 2026-12-19 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.

2026-12-19 → 2027-01-02 · $327.60

  • Southwest Airlines WN1111 / WN537: DEN 2026-12-19 10:45:00 → MDW 2026-12-19 16:55:00; 1 stop(s) via ICT; 310 minutes. Local airport times.
    • WN1111: DEN 2026-12-19 10:45:00 → ICT 2026-12-19 13:05:00; layover at ICT: 120 minutes.
    • WN537: ICT 2026-12-19 15:05:00 → MDW 2026-12-19 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.

2026-12-19 → 2027-01-02 · $327.60

  • Southwest Airlines WN878 / WN878: DEN 2026-12-19 14:25:00 → MDW 2026-12-19 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
    • WN878: DEN 2026-12-19 14:25:00 → CVG 2026-12-19 18:50:00; layover at CVG: 90 minutes.
    • WN878: CVG 2026-12-19 20:20:00 → MDW 2026-12-19 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.

2026-12-19 → 2027-01-02 · $327.60

  • Southwest Airlines WN1853 / WN1202: DEN 2026-12-19 11:15:00 → MDW 2026-12-19 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
    • WN1853: DEN 2026-12-19 11:15:00 → TUL 2026-12-19 13:55:00; layover at TUL: 70 minutes.
    • WN1202: TUL 2026-12-19 15:05:00 → MDW 2026-12-19 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.

2026-12-19 → 2027-01-02 · $341.60

  • Southwest Airlines WN1699: DEN 2026-12-19 14:50:00 → MDW 2026-12-19 18:05:00; nonstop; 135 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.

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