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Chicago → Denver

Jan 21, 2027 · return Jan 28, 2027

MDW → DEN1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
2:35 pmMDW
2h 40m
Nonstop
4:15 pmDEN
Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
10:50 amMDW
2h 40m
Nonstop
12:30 pmDEN
Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Thu, Jan 28

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

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
10:15 amMDW
5h 10m
OKC · 1h 15m
2:25 pmDEN
Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
1:50 pmMDW
5h 55m
CLE · 1h 15m
6:45 pmDEN
Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
9:50 amMDW
4h 55m
TUL · 1h 5m
1:45 pmDEN
Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
10:10 amMDW
5h 10m
MKE · 1h 45m
2:20 pmDEN
Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
5:10 pmMDW
5h 35m
MCI · 2h 15m
9:45 pmDEN
Southwest Airlines
2:40 pmDEN
2h 15m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ DEN

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)
2027-01-21 → 2027-01-28Southwest AirlinesWN4606 / WN1699$266.002026-10-29T01:29:06Z
2027-01-21 → 2027-01-28Southwest AirlinesWN120 / WN1699$266.002026-10-29T01:29:06Z
2027-01-21 → 2027-01-28Southwest AirlinesWN1523 + WN2509 / WN1699$256.502026-10-29T01:29:06Z
2027-01-21 → 2027-01-28Southwest AirlinesWN526 + WN3273 / WN1699$256.502026-10-29T01:29:06Z
2027-01-21 → 2027-01-28Southwest AirlinesWN4479 + WN757 / WN1699$256.502026-10-29T01:29:06Z
2027-01-21 → 2027-01-28Southwest AirlinesWN3051 + WN2162 / WN1699$256.502026-10-29T01:29:06Z
2027-01-21 → 2027-01-28Southwest AirlinesWN598 + WN32 / WN1699$256.502026-10-29T01:29:06Z
2027-01-21 → 2027-01-28Southwest AirlinesWN1742 + WN2668 / WN1699$256.502026-10-29T01:29:06Z

2027-01-21 → 2027-01-28 · $266.00

  • Southwest Airlines WN4606: MDW 2027-01-21 14:35:00 → DEN 2027-01-21 16:15:00; nonstop; 160 minutes. Local airport times.
  • Southwest Airlines WN1699: DEN 2027-01-28 14:40:00 → MDW 2027-01-28 17:55:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $266.00

  • Southwest Airlines WN120: MDW 2027-01-21 10:50:00 → DEN 2027-01-21 12:30:00; nonstop; 160 minutes. Local airport times.
  • Southwest Airlines WN1699: DEN 2027-01-28 14:40:00 → MDW 2027-01-28 17:55:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $256.50

  • Southwest Airlines WN1523 / WN2509: MDW 2027-01-21 10:05:00 → DEN 2027-01-21 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
    • WN1523: MDW 2027-01-21 10:05:00 → OMA 2027-01-21 11:40:00; layover at OMA: 115 minutes.
    • WN2509: OMA 2027-01-21 13:35:00 → DEN 2027-01-21 14:15:00.
  • Southwest Airlines WN1699: DEN 2027-01-28 14:40:00 → MDW 2027-01-28 17:55:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $256.50

  • Southwest Airlines WN526 / WN3273: MDW 2027-01-21 10:15:00 → DEN 2027-01-21 14:25:00; 1 stop(s) via OKC; 310 minutes. Local airport times.
    • WN526: MDW 2027-01-21 10:15:00 → OKC 2027-01-21 12:25:00; layover at OKC: 75 minutes.
    • WN3273: OKC 2027-01-21 13:40:00 → DEN 2027-01-21 14:25:00.
  • Southwest Airlines WN1699: DEN 2027-01-28 14:40:00 → MDW 2027-01-28 17:55:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $256.50

  • Southwest Airlines WN4479 / WN757: MDW 2027-01-21 13:50:00 → DEN 2027-01-21 18:45:00; 1 stop(s) via CLE; 355 minutes. Local airport times.
    • WN4479: MDW 2027-01-21 13:50:00 → CLE 2027-01-21 16:10:00; layover at CLE: 75 minutes.
    • WN757: CLE 2027-01-21 17:25:00 → DEN 2027-01-21 18:45:00.
  • Southwest Airlines WN1699: DEN 2027-01-28 14:40:00 → MDW 2027-01-28 17:55:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $256.50

  • Southwest Airlines WN3051 / WN2162: MDW 2027-01-21 09:50:00 → DEN 2027-01-21 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
    • WN3051: MDW 2027-01-21 09:50:00 → TUL 2027-01-21 11:50:00; layover at TUL: 65 minutes.
    • WN2162: TUL 2027-01-21 12:55:00 → DEN 2027-01-21 13:45:00.
  • Southwest Airlines WN1699: DEN 2027-01-28 14:40:00 → MDW 2027-01-28 17:55:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $256.50

  • Southwest Airlines WN598 / WN32: MDW 2027-01-21 10:10:00 → DEN 2027-01-21 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
    • WN598: MDW 2027-01-21 10:10:00 → MKE 2027-01-21 11:00:00; layover at MKE: 105 minutes.
    • WN32: MKE 2027-01-21 12:45:00 → DEN 2027-01-21 14:20:00.
  • Southwest Airlines WN1699: DEN 2027-01-28 14:40:00 → MDW 2027-01-28 17:55:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $256.50

  • Southwest Airlines WN1742 / WN2668: MDW 2027-01-21 17:10:00 → DEN 2027-01-21 21:45:00; 1 stop(s) via MCI; 335 minutes. Local airport times.
    • WN1742: MDW 2027-01-21 17:10:00 → MCI 2027-01-21 18:40:00; layover at MCI: 135 minutes.
    • WN2668: MCI 2027-01-21 20:55:00 → DEN 2027-01-21 21:45:00.
  • Southwest Airlines WN1699: DEN 2027-01-28 14:40:00 → MDW 2027-01-28 17:55:00; nonstop; 135 minutes. Local airport times.

More dates for this route