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Denver → Chicago

Dec 19, 2026 · return Dec 20, 2026

DEN → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Sat, Dec 19 – Sun, Dec 20

Southwest Airlines
8:45 amDEN
2h 20m
Nonstop
12:05 pmMDW
Southwest Airlines
4:25 pmMDW
2h 45m
Nonstop
6:10 pmDEN

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Sun, Dec 20

Southwest Airlines
2:50 pmDEN
2h 15m
Nonstop
6:05 pmMDW
Southwest Airlines
4:25 pmMDW
2h 45m
Nonstop
6:10 pmDEN

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Dec 19 – Sun, Dec 20

Southwest Airlines
10:45 amDEN
5h 10m
ICT · 2h
4:55 pmMDW
Southwest Airlines
4:25 pmMDW
2h 45m
Nonstop
6:10 pmDEN

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Sun, Dec 20

Southwest Airlines
11:25 amDEN
4h 45m
MCI · 1h 45m
5:10 pmMDW
Southwest Airlines
4:25 pmMDW
2h 45m
Nonstop
6:10 pmDEN

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Sun, Dec 20

Southwest Airlines
2:25 pmDEN
5h 5m
CVG · 1h 30m
8:30 pmMDW
Southwest Airlines
4:25 pmMDW
2h 45m
Nonstop
6:10 pmDEN

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Sun, Dec 20

Southwest Airlines
11:15 amDEN
4h 40m
TUL · 1h 10m
4:55 pmMDW
Southwest Airlines
4:25 pmMDW
2h 45m
Nonstop
6:10 pmDEN

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Sun, Dec 20

Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 pmMDW
Southwest Airlines
10:05 amMDW
5h 10m
OMA · 1h 55m
2:15 pmDEN

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Sun, Dec 20

Southwest Airlines
8:35 amDEN
4h 30m
COS · 1h 15m
2:05 pmMDW
Southwest Airlines
4:25 pmMDW
2h 45m
Nonstop
6:10 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
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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)
2026-12-19 → 2026-12-20Southwest AirlinesWN1697 / WN4606$364.002026-10-29T01:04:33Z
2026-12-19 → 2026-12-20Southwest AirlinesWN1699 / WN4606$364.002026-10-29T01:04:33Z
2026-12-19 → 2026-12-20Southwest AirlinesWN1111 + WN537 / WN4606$350.002026-10-29T01:04:33Z
2026-12-19 → 2026-12-20Southwest AirlinesWN1369 + WN2694 / WN4606$350.002026-10-29T01:04:33Z
2026-12-19 → 2026-12-20Southwest AirlinesWN878 + WN878 / WN4606$350.002026-10-29T01:04:33Z
2026-12-19 → 2026-12-20Southwest AirlinesWN1853 + WN1202 / WN4606$350.002026-10-29T01:04:33Z
2026-12-19 → 2026-12-20Southwest AirlinesWN1699 / WN1523 + WN2509$350.002026-10-29T01:04:33Z
2026-12-19 → 2026-12-20Southwest AirlinesWN1756 + WN4933 / WN4606$350.002026-10-29T01:04:33Z

2026-12-19 → 2026-12-20 · $364.00

  • Southwest Airlines WN1697: DEN 2026-12-19 08:45:00 → MDW 2026-12-19 12:05:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN4606: MDW 2026-12-20 16:25:00 → DEN 2026-12-20 18:10:00; nonstop; 165 minutes. Local airport times.

2026-12-19 → 2026-12-20 · $364.00

  • 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 WN4606: MDW 2026-12-20 16:25:00 → DEN 2026-12-20 18:10:00; nonstop; 165 minutes. Local airport times.

2026-12-19 → 2026-12-20 · $350.00

  • 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 WN4606: MDW 2026-12-20 16:25:00 → DEN 2026-12-20 18:10:00; nonstop; 165 minutes. Local airport times.

2026-12-19 → 2026-12-20 · $350.00

  • 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 WN4606: MDW 2026-12-20 16:25:00 → DEN 2026-12-20 18:10:00; nonstop; 165 minutes. Local airport times.

2026-12-19 → 2026-12-20 · $350.00

  • 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 WN4606: MDW 2026-12-20 16:25:00 → DEN 2026-12-20 18:10:00; nonstop; 165 minutes. Local airport times.

2026-12-19 → 2026-12-20 · $350.00

  • 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 WN4606: MDW 2026-12-20 16:25:00 → DEN 2026-12-20 18:10:00; nonstop; 165 minutes. Local airport times.

2026-12-19 → 2026-12-20 · $350.00

  • Southwest Airlines WN1699: DEN 2026-12-19 14:40:00 → MDW 2026-12-19 17:55:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN1523 / WN2509: MDW 2026-12-20 10:05:00 → DEN 2026-12-20 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
    • WN1523: MDW 2026-12-20 10:05:00 → OMA 2026-12-20 11:40:00; layover at OMA: 115 minutes.
    • WN2509: OMA 2026-12-20 13:35:00 → DEN 2026-12-20 14:15:00.

2026-12-19 → 2026-12-20 · $350.00

  • 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 WN4606: MDW 2026-12-20 16:25:00 → DEN 2026-12-20 18:10:00; nonstop; 165 minutes. Local airport times.

More dates for this route