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Denver → Chicago

Dec 16, 2026 · return Dec 26, 2026

DEN → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Wed, Dec 16 – Sat, Dec 26

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

Wed, Dec 16 – Sat, Dec 26

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

Wed, Dec 16 – Sat, Dec 26

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

Wed, Dec 16 – Sat, Dec 26

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

Wed, Dec 16 – Sat, Dec 26

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

Wed, Dec 16 – Sat, Dec 26

Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 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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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-16 → 2026-12-26Southwest AirlinesWN1853 + WN1202 / WN598 + WN32$288.002026-10-29T01:04:33Z
2026-12-16 → 2026-12-26Southwest AirlinesWN2832 + WN3127 / WN598 + WN32$288.002026-10-29T01:04:33Z
2026-12-16 → 2026-12-26Southwest AirlinesWN1756 + WN4933 / WN598 + WN32$288.002026-10-29T01:04:33Z
2026-12-16 → 2026-12-26Southwest AirlinesWN878 + WN878 / WN598 + WN32$288.002026-10-29T01:04:33Z
2026-12-16 → 2026-12-26Southwest AirlinesWN1369 + WN2694 / WN598 + WN32$288.002026-10-29T01:04:33Z
2026-12-16 → 2026-12-26Southwest AirlinesWN1699 / WN598 + WN32$298.002026-10-29T01:04:33Z

2026-12-16 → 2026-12-26 · $288.00

  • Southwest Airlines WN1853 / WN1202: DEN 2026-12-16 11:15:00 → MDW 2026-12-16 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
    • WN1853: DEN 2026-12-16 11:15:00 → TUL 2026-12-16 13:55:00; layover at TUL: 70 minutes.
    • WN1202: TUL 2026-12-16 15:05:00 → MDW 2026-12-16 16:55:00.
  • Southwest Airlines WN598 / WN32: MDW 2026-12-26 10:10:00 → DEN 2026-12-26 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2026-12-26 10:10:00 → MKE 2026-12-26 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2026-12-26 12:45:00 → DEN 2026-12-26 14:20:00.

2026-12-16 → 2026-12-26 · $288.00

  • Southwest Airlines WN2832 / WN3127: DEN 2026-12-16 11:05:00 → MDW 2026-12-16 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
    • WN2832: DEN 2026-12-16 11:05:00 → MSP 2026-12-16 14:05:00; layover at MSP: 85 minutes.
    • WN3127: MSP 2026-12-16 15:30:00 → MDW 2026-12-16 17:15:00.
  • Southwest Airlines WN598 / WN32: MDW 2026-12-26 10:10:00 → DEN 2026-12-26 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2026-12-26 10:10:00 → MKE 2026-12-26 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2026-12-26 12:45:00 → DEN 2026-12-26 14:20:00.

2026-12-16 → 2026-12-26 · $288.00

  • Southwest Airlines WN1756 / WN4933: DEN 2026-12-16 08:35:00 → MDW 2026-12-16 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
    • WN1756: DEN 2026-12-16 08:35:00 → COS 2026-12-16 09:25:00; layover at COS: 75 minutes.
    • WN4933: COS 2026-12-16 10:40:00 → MDW 2026-12-16 14:05:00.
  • Southwest Airlines WN598 / WN32: MDW 2026-12-26 10:10:00 → DEN 2026-12-26 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2026-12-26 10:10:00 → MKE 2026-12-26 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2026-12-26 12:45:00 → DEN 2026-12-26 14:20:00.

2026-12-16 → 2026-12-26 · $288.00

  • Southwest Airlines WN878 / WN878: DEN 2026-12-16 14:25:00 → MDW 2026-12-16 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
    • WN878: DEN 2026-12-16 14:25:00 → CVG 2026-12-16 18:50:00; layover at CVG: 90 minutes.
    • WN878: CVG 2026-12-16 20:20:00 → MDW 2026-12-16 20:30:00.
  • Southwest Airlines WN598 / WN32: MDW 2026-12-26 10:10:00 → DEN 2026-12-26 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2026-12-26 10:10:00 → MKE 2026-12-26 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2026-12-26 12:45:00 → DEN 2026-12-26 14:20:00.

2026-12-16 → 2026-12-26 · $288.00

  • Southwest Airlines WN1369 / WN2694: DEN 2026-12-16 11:25:00 → MDW 2026-12-16 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
    • WN1369: DEN 2026-12-16 11:25:00 → MCI 2026-12-16 14:05:00; layover at MCI: 105 minutes.
    • WN2694: MCI 2026-12-16 15:50:00 → MDW 2026-12-16 17:10:00.
  • Southwest Airlines WN598 / WN32: MDW 2026-12-26 10:10:00 → DEN 2026-12-26 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2026-12-26 10:10:00 → MKE 2026-12-26 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2026-12-26 12:45:00 → DEN 2026-12-26 14:20:00.

2026-12-16 → 2026-12-26 · $298.00

  • Southwest Airlines WN1699: DEN 2026-12-16 14:40:00 → MDW 2026-12-16 17:55:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN598 / WN32: MDW 2026-12-26 10:10:00 → DEN 2026-12-26 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2026-12-26 10:10:00 → MKE 2026-12-26 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2026-12-26 12:45:00 → DEN 2026-12-26 14:20:00.

More dates for this route