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Chicago → Cancun

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MDW → CUN1 adulteconomy

18 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
3:45 pmMDW
3h 40m
Nonstop
8:25 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
1:02 pmMDW
7h 6m
ATL · 2h 28m
9:08 pmCUN
Delta Air Lines
4:20 pmCUN
7h 2m
ATL · 2h 20m
10:22 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:45 pmMDW
3h 40m
Nonstop
8:25 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
10:15 amMDW
8h 30m
HOU · 3h 45m
7:45 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:35 amMDW
6h 25m
MCI · 1h 40m
3:00 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:35 amMDW
8h 50m
MCO · 4h
4:25 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
8:50 amMDW
8h 5m
BWI · 2h 30m
5:55 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:50 amMDW
8h 5m
BWI · 2h 30m
5:55 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Show 4 more flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:35 amMDW
6h 25m
MCI · 1h 40m
3:00 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:15 amMDW
8h 30m
HOU · 3h 45m
7:45 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:35 amMDW
8h 50m
MCO · 4h
4:25 pmCUN
Southwest Airlines
8:20 amCUN
3h 30m
Nonstop
10:50 amMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
1:02 pmMDW
7h 6m
ATL · 2h 28m
9:08 pmCUN
Delta Air Lines
4:20 pmCUN
7h 2m
ATL · 2h 20m
10:22 pmMDW

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
3:45 pmMDW
3h 40m
Nonstop
8:25 pmCUN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
1:02 pmMDW
7h 6m
ATL · 2h 28m
9:08 pmCUN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
8:50 amMDW
8h 5m
BWI · 2h 30m
5:55 pmCUN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:15 amMDW
8h 30m
HOU · 3h 45m
7:45 pmCUN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
6:35 amMDW
8h 50m
MCO · 4h
4:25 pmCUN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:35 amMDW
6h 25m
MCI · 1h 40m
3:00 pmCUN

One-way total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ CUN

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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  • 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
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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 AirlinesWN218$223.252026-10-29T01:29:05Z
2026-11-20 → 2026-11-23Southwest AirlinesWN218 / WN219$463.282026-10-29T01:29:05Z
2026-11-20 · one wayDelta Air LinesDL2417 + DL1939$232.752026-10-29T01:29:05Z
2026-11-20 → 2026-11-23Delta Air LinesDL2417 + DL1939 / DL1962 + DL1076$473.932026-10-29T01:29:05Z
2026-11-27 → 2026-12-04Southwest AirlinesWN218 / WN219$474.152026-10-29T01:29:05Z
2026-11-20 · one waySouthwest AirlinesWN1123 + WN1609$199.502026-10-29T01:29:05Z
2026-11-20 · one waySouthwest AirlinesWN4395 + WN305$199.502026-10-29T01:29:05Z
2026-11-20 · one waySouthwest AirlinesWN2964 + WN923$199.502026-10-29T01:29:05Z
2026-11-20 · one waySouthwest AirlinesWN2959 + WN144$199.502026-10-29T01:29:05Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4395 + WN305 / WN219$439.532026-10-29T01:29:05Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2959 + WN144 / WN219$439.532026-10-29T01:29:05Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2964 + WN923 / WN219$439.532026-10-29T01:29:05Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1123 + WN1609 / WN219$439.532026-10-29T01:29:05Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1123 + WN1609 / WN219$444.652026-10-29T01:29:05Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2959 + WN144 / WN219$444.652026-10-29T01:29:05Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4395 + WN305 / WN219$444.652026-10-29T01:29:05Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2964 + WN923 / WN219$444.652026-10-29T01:29:05Z
2026-11-27 → 2026-12-04Delta Air LinesDL2417 + DL1939 / DL1962 + DL1076$485.052026-10-29T01:29:05Z

2026-11-20 · one way · $223.25

  • Southwest Airlines WN218: MDW 2026-11-20 15:45:00 → CUN 2026-11-20 20:25:00; nonstop; 220 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $463.28

  • Southwest Airlines WN218: MDW 2026-11-20 15:45:00 → CUN 2026-11-20 20:25:00; nonstop; 220 minutes. Local airport times.
  • Southwest Airlines WN219: CUN 2026-11-23 08:20:00 → MDW 2026-11-23 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-20 · one way · $232.75

  • Delta Air Lines DL2417 / DL1939: MDW 2026-11-20 13:02:00 → CUN 2026-11-20 21:08:00; 1 stop(s) via ATL; 426 minutes. Local airport times.
    • DL2417: MDW 2026-11-20 13:02:00 → ATL 2026-11-20 16:01:00; layover at ATL: 148 minutes.
    • DL1939: ATL 2026-11-20 18:29:00 → CUN 2026-11-20 21:08:00.

2026-11-20 → 2026-11-23 · $473.93

  • Delta Air Lines DL2417 / DL1939: MDW 2026-11-20 13:02:00 → CUN 2026-11-20 21:08:00; 1 stop(s) via ATL; 426 minutes. Local airport times.
    • DL2417: MDW 2026-11-20 13:02:00 → ATL 2026-11-20 16:01:00; layover at ATL: 148 minutes.
    • DL1939: ATL 2026-11-20 18:29:00 → CUN 2026-11-20 21:08:00.
  • Delta Air Lines DL1962 / DL1076: CUN 2026-11-23 16:20:00 → MDW 2026-11-23 22:22:00; 1 stop(s) via ATL; 422 minutes. Local airport times.
    • DL1962: CUN 2026-11-23 16:20:00 → ATL 2026-11-23 19:05:00; layover at ATL: 140 minutes.
    • DL1076: ATL 2026-11-23 21:25:00 → MDW 2026-11-23 22:22:00.

2026-11-27 → 2026-12-04 · $474.15

  • Southwest Airlines WN218: MDW 2026-11-27 15:45:00 → CUN 2026-11-27 20:25:00; nonstop; 220 minutes. Local airport times.
  • Southwest Airlines WN219: CUN 2026-12-04 08:20:00 → MDW 2026-12-04 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-20 · one way · $199.50

  • Southwest Airlines WN1123 / WN1609: MDW 2026-11-20 08:50:00 → CUN 2026-11-20 17:55:00; 1 stop(s) via BWI; 485 minutes. Local airport times.
    • WN1123: MDW 2026-11-20 08:50:00 → BWI 2026-11-20 11:40:00; layover at BWI: 150 minutes.
    • WN1609: BWI 2026-11-20 14:10:00 → CUN 2026-11-20 17:55:00.

2026-11-20 · one way · $199.50

  • Southwest Airlines WN4395 / WN305: MDW 2026-11-20 10:15:00 → CUN 2026-11-20 19:45:00; 1 stop(s) via HOU; 510 minutes. Local airport times.
    • WN4395: MDW 2026-11-20 10:15:00 → HOU 2026-11-20 12:50:00; layover at HOU: 225 minutes.
    • WN305: HOU 2026-11-20 16:35:00 → CUN 2026-11-20 19:45:00.

2026-11-20 · one way · $199.50

  • Southwest Airlines WN2964 / WN923: MDW 2026-11-20 06:35:00 → CUN 2026-11-20 16:25:00; 1 stop(s) via MCO; 530 minutes. Local airport times.
    • WN2964: MDW 2026-11-20 06:35:00 → MCO 2026-11-20 10:20:00; layover at MCO: 240 minutes.
    • WN923: MCO 2026-11-20 14:20:00 → CUN 2026-11-20 16:25:00.

2026-11-20 · one way · $199.50

  • Southwest Airlines WN2959 / WN144: MDW 2026-11-20 07:35:00 → CUN 2026-11-20 15:00:00; 1 stop(s) via MCI; 385 minutes. Local airport times.
    • WN2959: MDW 2026-11-20 07:35:00 → MCI 2026-11-20 09:05:00; layover at MCI: 100 minutes.
    • WN144: MCI 2026-11-20 10:45:00 → CUN 2026-11-20 15:00:00.

2026-11-20 → 2026-11-23 · $439.53

  • Southwest Airlines WN4395 / WN305: MDW 2026-11-20 10:15:00 → CUN 2026-11-20 19:45:00; 1 stop(s) via HOU; 510 minutes. Local airport times.
    • WN4395: MDW 2026-11-20 10:15:00 → HOU 2026-11-20 12:50:00; layover at HOU: 225 minutes.
    • WN305: HOU 2026-11-20 16:35:00 → CUN 2026-11-20 19:45:00.
  • Southwest Airlines WN219: CUN 2026-11-23 08:20:00 → MDW 2026-11-23 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $439.53

  • Southwest Airlines WN2959 / WN144: MDW 2026-11-20 07:35:00 → CUN 2026-11-20 15:00:00; 1 stop(s) via MCI; 385 minutes. Local airport times.
    • WN2959: MDW 2026-11-20 07:35:00 → MCI 2026-11-20 09:05:00; layover at MCI: 100 minutes.
    • WN144: MCI 2026-11-20 10:45:00 → CUN 2026-11-20 15:00:00.
  • Southwest Airlines WN219: CUN 2026-11-23 08:20:00 → MDW 2026-11-23 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $439.53

  • Southwest Airlines WN2964 / WN923: MDW 2026-11-20 06:35:00 → CUN 2026-11-20 16:25:00; 1 stop(s) via MCO; 530 minutes. Local airport times.
    • WN2964: MDW 2026-11-20 06:35:00 → MCO 2026-11-20 10:20:00; layover at MCO: 240 minutes.
    • WN923: MCO 2026-11-20 14:20:00 → CUN 2026-11-20 16:25:00.
  • Southwest Airlines WN219: CUN 2026-11-23 08:20:00 → MDW 2026-11-23 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $439.53

  • Southwest Airlines WN1123 / WN1609: MDW 2026-11-20 08:50:00 → CUN 2026-11-20 17:55:00; 1 stop(s) via BWI; 485 minutes. Local airport times.
    • WN1123: MDW 2026-11-20 08:50:00 → BWI 2026-11-20 11:40:00; layover at BWI: 150 minutes.
    • WN1609: BWI 2026-11-20 14:10:00 → CUN 2026-11-20 17:55:00.
  • Southwest Airlines WN219: CUN 2026-11-23 08:20:00 → MDW 2026-11-23 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $444.65

  • Southwest Airlines WN1123 / WN1609: MDW 2026-11-27 08:50:00 → CUN 2026-11-27 17:55:00; 1 stop(s) via BWI; 485 minutes. Local airport times.
    • WN1123: MDW 2026-11-27 08:50:00 → BWI 2026-11-27 11:40:00; layover at BWI: 150 minutes.
    • WN1609: BWI 2026-11-27 14:10:00 → CUN 2026-11-27 17:55:00.
  • Southwest Airlines WN219: CUN 2026-12-04 08:20:00 → MDW 2026-12-04 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $444.65

  • Southwest Airlines WN2959 / WN144: MDW 2026-11-27 07:35:00 → CUN 2026-11-27 15:00:00; 1 stop(s) via MCI; 385 minutes. Local airport times.
    • WN2959: MDW 2026-11-27 07:35:00 → MCI 2026-11-27 09:05:00; layover at MCI: 100 minutes.
    • WN144: MCI 2026-11-27 10:45:00 → CUN 2026-11-27 15:00:00.
  • Southwest Airlines WN219: CUN 2026-12-04 08:20:00 → MDW 2026-12-04 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $444.65

  • Southwest Airlines WN4395 / WN305: MDW 2026-11-27 10:15:00 → CUN 2026-11-27 19:45:00; 1 stop(s) via HOU; 510 minutes. Local airport times.
    • WN4395: MDW 2026-11-27 10:15:00 → HOU 2026-11-27 12:50:00; layover at HOU: 225 minutes.
    • WN305: HOU 2026-11-27 16:35:00 → CUN 2026-11-27 19:45:00.
  • Southwest Airlines WN219: CUN 2026-12-04 08:20:00 → MDW 2026-12-04 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $444.65

  • Southwest Airlines WN2964 / WN923: MDW 2026-11-27 06:35:00 → CUN 2026-11-27 16:25:00; 1 stop(s) via MCO; 530 minutes. Local airport times.
    • WN2964: MDW 2026-11-27 06:35:00 → MCO 2026-11-27 10:20:00; layover at MCO: 240 minutes.
    • WN923: MCO 2026-11-27 14:20:00 → CUN 2026-11-27 16:25:00.
  • Southwest Airlines WN219: CUN 2026-12-04 08:20:00 → MDW 2026-12-04 10:50:00; nonstop; 210 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $485.05

  • Delta Air Lines DL2417 / DL1939: MDW 2026-11-27 13:02:00 → CUN 2026-11-27 21:08:00; 1 stop(s) via ATL; 426 minutes. Local airport times.
    • DL2417: MDW 2026-11-27 13:02:00 → ATL 2026-11-27 16:01:00; layover at ATL: 148 minutes.
    • DL1939: ATL 2026-11-27 18:29:00 → CUN 2026-11-27 21:08:00.
  • Delta Air Lines DL1962 / DL1076: CUN 2026-12-04 16:20:00 → MDW 2026-12-04 22:22:00; 1 stop(s) via ATL; 422 minutes. Local airport times.
    • DL1962: CUN 2026-12-04 16:20:00 → ATL 2026-12-04 19:05:00; layover at ATL: 140 minutes.
    • DL1076: ATL 2026-12-04 21:25:00 → MDW 2026-12-04 22:22:00.

More dates for this route