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Denver → Chicago

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DEN → MDW1 adulteconomy

22 flight options · 1 airline

Round-trip flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:55 amDEN
2h 20m
Nonstop
12:15 pmMDW
Southwest Airlines
10:50 amMDW
2h 40m
Nonstop
12:30 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
11:05 amDEN
5h 10m
MSP · 1h 25m
5:15 pmMDW
Southwest Airlines
9:50 amMDW
4h 55m
TUL · 1h 5m
1:45 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:45 amDEN
5h 10m
ICT · 2h
4:55 pmMDW
Southwest Airlines
10:50 amMDW
2h 40m
Nonstop
12:30 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
11:15 amDEN
4h 40m
TUL · 1h 10m
4:55 pmMDW
Southwest Airlines
10:50 amMDW
2h 40m
Nonstop
12:30 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:25 pmDEN
5h 5m
CVG · 1h 30m
8:30 pmMDW
Southwest Airlines
10:50 amMDW
2h 40m
Nonstop
12:30 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
11:05 amDEN
5h 10m
MSP · 1h 25m
5:15 pmMDW
Southwest Airlines
10:50 amMDW
2h 40m
Nonstop
12:30 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
11:25 amDEN
4h 45m
MCI · 1h 45m
5:10 pmMDW
Southwest Airlines
10:50 amMDW
2h 40m
Nonstop
12:30 pmDEN

Round-trip total · 1 adult · Taxes included

Show 6 more flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:35 amDEN
4h 30m
COS · 1h 15m
2:05 pmMDW
Southwest Airlines
10:50 amMDW
2h 40m
Nonstop
12:30 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
11:15 amDEN
4h 40m
TUL · 1h 10m
4:55 pmMDW
Southwest Airlines
9:50 amMDW
4h 55m
TUL · 1h 5m
1:45 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
2:25 pmDEN
5h 5m
CVG · 1h 30m
8:30 pmMDW
Southwest Airlines
9:50 amMDW
4h 55m
TUL · 1h 5m
1:45 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
8:35 amDEN
4h 30m
COS · 1h 15m
2:05 pmMDW
Southwest Airlines
9:50 amMDW
4h 55m
TUL · 1h 5m
1:45 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
11:25 amDEN
4h 45m
MCI · 1h 45m
5:10 pmMDW
Southwest Airlines
9:50 amMDW
4h 55m
TUL · 1h 5m
1:45 pmDEN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
8:55 amDEN
2h 20m
Nonstop
12:15 pmMDW
Southwest Airlines
9:50 amMDW
4h 55m
TUL · 1h 5m
1:45 pmDEN

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
8:55 amDEN
2h 20m
Nonstop
12:15 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
11:05 amDEN
5h 10m
MSP · 1h 25m
5:15 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:45 amDEN
5h 10m
ICT · 2h
4:55 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
11:15 amDEN
4h 40m
TUL · 1h 10m
4:55 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
8:35 amDEN
4h 30m
COS · 1h 15m
2:05 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:25 pmDEN
5h 5m
CVG · 1h 30m
8:30 pmMDW

One-way 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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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 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)
2026-11-20 · one waySouthwest AirlinesWN1697$182.252026-10-29T01:04:33Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1697 / WN120$305.502026-10-29T01:04:33Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2832 + WN3127 / WN3051 + WN2162$324.002026-10-29T01:04:33Z
2026-11-20 · one waySouthwest AirlinesWN1699$182.252026-10-29T01:04:33Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1699 / WN120$305.502026-10-29T01:04:33Z
2026-11-20 · one waySouthwest AirlinesWN1369 + WN2694$168.752026-10-29T01:04:33Z
2026-11-20 · one waySouthwest AirlinesWN2832 + WN3127$168.752026-10-29T01:04:33Z
2026-11-20 · one waySouthwest AirlinesWN1111 + WN537$168.752026-10-29T01:04:33Z
2026-11-20 · one waySouthwest AirlinesWN1853 + WN1202$168.752026-10-29T01:04:33Z
2026-11-20 · one waySouthwest AirlinesWN1756 + WN4933$168.752026-10-29T01:04:33Z
2026-11-20 · one waySouthwest AirlinesWN878 + WN878$168.752026-10-29T01:04:33Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1111 + WN537 / WN120$292.002026-10-29T01:04:33Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1853 + WN1202 / WN120$292.002026-10-29T01:04:33Z
2026-11-27 → 2026-12-04Southwest AirlinesWN878 + WN878 / WN120$292.002026-10-29T01:04:33Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2832 + WN3127 / WN120$292.002026-10-29T01:04:33Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1369 + WN2694 / WN120$292.002026-10-29T01:04:33Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1756 + WN4933 / WN120$292.002026-10-29T01:04:33Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1853 + WN1202 / WN3051 + WN2162$324.002026-10-29T01:04:33Z
2026-11-20 → 2026-11-23Southwest AirlinesWN878 + WN878 / WN3051 + WN2162$324.002026-10-29T01:04:33Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1756 + WN4933 / WN3051 + WN2162$324.002026-10-29T01:04:33Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1369 + WN2694 / WN3051 + WN2162$324.002026-10-29T01:04:33Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1697 / WN3051 + WN2162$337.502026-10-29T01:04:33Z

2026-11-20 · one way · $182.25

  • Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $305.50

  • Southwest Airlines WN1697: DEN 2026-11-27 08:55:00 → MDW 2026-11-27 12:15:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $324.00

  • Southwest Airlines WN2832 / WN3127: DEN 2026-11-20 11:05:00 → MDW 2026-11-20 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
    • WN2832: DEN 2026-11-20 11:05:00 → MSP 2026-11-20 14:05:00; layover at MSP: 85 minutes.
    • WN3127: MSP 2026-11-20 15:30:00 → MDW 2026-11-20 17:15:00.
  • Southwest Airlines WN3051 / WN2162: MDW 2026-11-23 09:50:00 → DEN 2026-11-23 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
    • WN3051: MDW 2026-11-23 09:50:00 → TUL 2026-11-23 11:50:00; layover at TUL: 65 minutes.
    • WN2162: TUL 2026-11-23 12:55:00 → DEN 2026-11-23 13:45:00.

2026-11-20 · one way · $182.25

  • Southwest Airlines WN1699: DEN 2026-11-20 14:40:00 → MDW 2026-11-20 17:55:00; nonstop; 135 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $305.50

  • Southwest Airlines WN1699: DEN 2026-11-27 14:40:00 → MDW 2026-11-27 17:55:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-20 · one way · $168.75

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

2026-11-20 · one way · $168.75

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

2026-11-20 · one way · $168.75

  • Southwest Airlines WN1111 / WN537: DEN 2026-11-20 10:45:00 → MDW 2026-11-20 16:55:00; 1 stop(s) via ICT; 310 minutes. Local airport times.
    • WN1111: DEN 2026-11-20 10:45:00 → ICT 2026-11-20 13:05:00; layover at ICT: 120 minutes.
    • WN537: ICT 2026-11-20 15:05:00 → MDW 2026-11-20 16:55:00.

2026-11-20 · one way · $168.75

  • Southwest Airlines WN1853 / WN1202: DEN 2026-11-20 11:15:00 → MDW 2026-11-20 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
    • WN1853: DEN 2026-11-20 11:15:00 → TUL 2026-11-20 13:55:00; layover at TUL: 70 minutes.
    • WN1202: TUL 2026-11-20 15:05:00 → MDW 2026-11-20 16:55:00.

2026-11-20 · one way · $168.75

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

2026-11-20 · one way · $168.75

  • Southwest Airlines WN878 / WN878: DEN 2026-11-20 14:25:00 → MDW 2026-11-20 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
    • WN878: DEN 2026-11-20 14:25:00 → CVG 2026-11-20 18:50:00; layover at CVG: 90 minutes.
    • WN878: CVG 2026-11-20 20:20:00 → MDW 2026-11-20 20:30:00.

2026-11-27 → 2026-12-04 · $292.00

  • Southwest Airlines WN1111 / WN537: DEN 2026-11-27 10:45:00 → MDW 2026-11-27 16:55:00; 1 stop(s) via ICT; 310 minutes. Local airport times.
    • WN1111: DEN 2026-11-27 10:45:00 → ICT 2026-11-27 13:05:00; layover at ICT: 120 minutes.
    • WN537: ICT 2026-11-27 15:05:00 → MDW 2026-11-27 16:55:00.
  • Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $292.00

  • Southwest Airlines WN1853 / WN1202: DEN 2026-11-27 11:15:00 → MDW 2026-11-27 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
    • WN1853: DEN 2026-11-27 11:15:00 → TUL 2026-11-27 13:55:00; layover at TUL: 70 minutes.
    • WN1202: TUL 2026-11-27 15:05:00 → MDW 2026-11-27 16:55:00.
  • Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $292.00

  • Southwest Airlines WN878 / WN878: DEN 2026-11-27 14:25:00 → MDW 2026-11-27 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
    • WN878: DEN 2026-11-27 14:25:00 → CVG 2026-11-27 18:50:00; layover at CVG: 90 minutes.
    • WN878: CVG 2026-11-27 20:20:00 → MDW 2026-11-27 20:30:00.
  • Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $292.00

  • Southwest Airlines WN2832 / WN3127: DEN 2026-11-27 11:05:00 → MDW 2026-11-27 17:15:00; 1 stop(s) via MSP; 310 minutes. Local airport times.
    • WN2832: DEN 2026-11-27 11:05:00 → MSP 2026-11-27 14:05:00; layover at MSP: 85 minutes.
    • WN3127: MSP 2026-11-27 15:30:00 → MDW 2026-11-27 17:15:00.
  • Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $292.00

  • Southwest Airlines WN1369 / WN2694: DEN 2026-11-27 11:25:00 → MDW 2026-11-27 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
    • WN1369: DEN 2026-11-27 11:25:00 → MCI 2026-11-27 14:05:00; layover at MCI: 105 minutes.
    • WN2694: MCI 2026-11-27 15:50:00 → MDW 2026-11-27 17:10:00.
  • Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $292.00

  • Southwest Airlines WN1756 / WN4933: DEN 2026-11-27 08:35:00 → MDW 2026-11-27 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
    • WN1756: DEN 2026-11-27 08:35:00 → COS 2026-11-27 09:25:00; layover at COS: 75 minutes.
    • WN4933: COS 2026-11-27 10:40:00 → MDW 2026-11-27 14:05:00.
  • Southwest Airlines WN120: MDW 2026-12-04 10:50:00 → DEN 2026-12-04 12:30:00; nonstop; 160 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $324.00

  • Southwest Airlines WN1853 / WN1202: DEN 2026-11-20 11:15:00 → MDW 2026-11-20 16:55:00; 1 stop(s) via TUL; 280 minutes. Local airport times.
    • WN1853: DEN 2026-11-20 11:15:00 → TUL 2026-11-20 13:55:00; layover at TUL: 70 minutes.
    • WN1202: TUL 2026-11-20 15:05:00 → MDW 2026-11-20 16:55:00.
  • Southwest Airlines WN3051 / WN2162: MDW 2026-11-23 09:50:00 → DEN 2026-11-23 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
    • WN3051: MDW 2026-11-23 09:50:00 → TUL 2026-11-23 11:50:00; layover at TUL: 65 minutes.
    • WN2162: TUL 2026-11-23 12:55:00 → DEN 2026-11-23 13:45:00.

2026-11-20 → 2026-11-23 · $324.00

  • Southwest Airlines WN878 / WN878: DEN 2026-11-20 14:25:00 → MDW 2026-11-20 20:30:00; 1 stop(s) via CVG; 305 minutes. Local airport times.
    • WN878: DEN 2026-11-20 14:25:00 → CVG 2026-11-20 18:50:00; layover at CVG: 90 minutes.
    • WN878: CVG 2026-11-20 20:20:00 → MDW 2026-11-20 20:30:00.
  • Southwest Airlines WN3051 / WN2162: MDW 2026-11-23 09:50:00 → DEN 2026-11-23 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
    • WN3051: MDW 2026-11-23 09:50:00 → TUL 2026-11-23 11:50:00; layover at TUL: 65 minutes.
    • WN2162: TUL 2026-11-23 12:55:00 → DEN 2026-11-23 13:45:00.

2026-11-20 → 2026-11-23 · $324.00

  • Southwest Airlines WN1756 / WN4933: DEN 2026-11-20 08:35:00 → MDW 2026-11-20 14:05:00; 1 stop(s) via COS; 270 minutes. Local airport times.
    • WN1756: DEN 2026-11-20 08:35:00 → COS 2026-11-20 09:25:00; layover at COS: 75 minutes.
    • WN4933: COS 2026-11-20 10:40:00 → MDW 2026-11-20 14:05:00.
  • Southwest Airlines WN3051 / WN2162: MDW 2026-11-23 09:50:00 → DEN 2026-11-23 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
    • WN3051: MDW 2026-11-23 09:50:00 → TUL 2026-11-23 11:50:00; layover at TUL: 65 minutes.
    • WN2162: TUL 2026-11-23 12:55:00 → DEN 2026-11-23 13:45:00.

2026-11-20 → 2026-11-23 · $324.00

  • Southwest Airlines WN1369 / WN2694: DEN 2026-11-20 11:25:00 → MDW 2026-11-20 17:10:00; 1 stop(s) via MCI; 285 minutes. Local airport times.
    • WN1369: DEN 2026-11-20 11:25:00 → MCI 2026-11-20 14:05:00; layover at MCI: 105 minutes.
    • WN2694: MCI 2026-11-20 15:50:00 → MDW 2026-11-20 17:10:00.
  • Southwest Airlines WN3051 / WN2162: MDW 2026-11-23 09:50:00 → DEN 2026-11-23 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
    • WN3051: MDW 2026-11-23 09:50:00 → TUL 2026-11-23 11:50:00; layover at TUL: 65 minutes.
    • WN2162: TUL 2026-11-23 12:55:00 → DEN 2026-11-23 13:45:00.

2026-11-20 → 2026-11-23 · $337.50

  • Southwest Airlines WN1697: DEN 2026-11-20 08:55:00 → MDW 2026-11-20 12:15:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN3051 / WN2162: MDW 2026-11-23 09:50:00 → DEN 2026-11-23 13:45:00; 1 stop(s) via TUL; 295 minutes. Local airport times.
    • WN3051: MDW 2026-11-23 09:50:00 → TUL 2026-11-23 11:50:00; layover at TUL: 65 minutes.
    • WN2162: TUL 2026-11-23 12:55:00 → DEN 2026-11-23 13:45:00.

More dates for this route