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Kansas City → Chicago

Jan 21, 2027 · return Feb 4, 2027

MCI → MDW1 adulteconomyRound trip

6 flight options · 2 airlines

Nonstop flights

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
5:35 amMCI
1h 25m
Nonstop
7:00 amMDW
Southwest Airlines
11:45 amMDW
1h 30m
Nonstop
1:15 pmMCI

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
3:50 pmMCI
1h 20m
Nonstop
5:10 pmMDW
Southwest Airlines
11:45 amMDW
1h 30m
Nonstop
1:15 pmMCI

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Thu, Feb 4

Delta Air Lines
10:43 amMCI
5h 56m
MSP · 2h 45m
4:39 pmMDW
Delta Air Lines
10:24 amMDW
6h 32m
MSP · 3h
4:56 pmMCI

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
1:25 pmMCI
4h 25m
IND · 1h 55m
5:50 pmMDW
Southwest Airlines
11:45 amMDW
1h 30m
Nonstop
1:15 pmMCI

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
6:05 pmMCI
4h 55m
STL · 2h 40m
11:00 pmMDW
Southwest Airlines
11:45 amMDW
1h 30m
Nonstop
1:15 pmMCI

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
12:10 pmMCI
5h 5m
MKE · 2h 40m
5:15 pmMDW
Southwest Airlines
11:45 amMDW
1h 30m
Nonstop
1:15 pmMCI

Round-trip total · 1 adult · Taxes included

Make this trip yours

MCI ⇄ 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)
2027-01-21 → 2027-02-04Southwest AirlinesWN2690 / WN1369$226.102026-10-29T01:28:08Z
2027-01-21 → 2027-02-04Delta Air LinesDL3799 + DL4714 / DL5469 + DL5401$349.602026-10-29T01:28:08Z
2027-01-21 → 2027-02-04Southwest AirlinesWN2694 / WN1369$226.102026-10-29T01:28:08Z
2027-01-21 → 2027-02-04Southwest AirlinesWN1418 + WN2224 / WN1369$249.852026-10-29T01:28:08Z
2027-01-21 → 2027-02-04Southwest AirlinesWN2715 + WN4770 / WN1369$249.852026-10-29T01:28:08Z
2027-01-21 → 2027-02-04Southwest AirlinesWN294 + WN22 / WN1369$249.852026-10-29T01:28:08Z

2027-01-21 → 2027-02-04 · $226.10

  • Southwest Airlines WN2690: MCI 2027-01-21 05:35:00 → MDW 2027-01-21 07:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1369: MDW 2027-02-04 11:45:00 → MCI 2027-02-04 13:15:00; nonstop; 90 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $349.60

  • Delta Air Lines DL3799 / DL4714: MCI 2027-01-21 10:43:00 → MDW 2027-01-21 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
    • DL3799: MCI 2027-01-21 10:43:00 → MSP 2027-01-21 12:15:00; layover at MSP: 165 minutes.
    • DL4714: MSP 2027-01-21 15:00:00 → MDW 2027-01-21 16:39:00.
  • Delta Air Lines DL5469 / DL5401: MDW 2027-02-04 10:24:00 → MCI 2027-02-04 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
    • DL5469: MDW 2027-02-04 10:24:00 → MSP 2027-02-04 12:09:00; layover at MSP: 180 minutes.
    • DL5401: MSP 2027-02-04 15:09:00 → MCI 2027-02-04 16:56:00.

2027-01-21 → 2027-02-04 · $226.10

  • Southwest Airlines WN2694: MCI 2027-01-21 15:50:00 → MDW 2027-01-21 17:10:00; nonstop; 80 minutes. Local airport times.
  • Southwest Airlines WN1369: MDW 2027-02-04 11:45:00 → MCI 2027-02-04 13:15:00; nonstop; 90 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $249.85

  • Southwest Airlines WN1418 / WN2224: MCI 2027-01-21 13:25:00 → MDW 2027-01-21 17:50:00; 1 stop(s) via IND; 265 minutes. Local airport times.
    • WN1418: MCI 2027-01-21 13:25:00 → IND 2027-01-21 15:45:00; layover at IND: 115 minutes.
    • WN2224: IND 2027-01-21 17:40:00 → MDW 2027-01-21 17:50:00.
  • Southwest Airlines WN1369: MDW 2027-02-04 11:45:00 → MCI 2027-02-04 13:15:00; nonstop; 90 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $249.85

  • Southwest Airlines WN2715 / WN4770: MCI 2027-01-21 18:05:00 → MDW 2027-01-21 23:00:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2715: MCI 2027-01-21 18:05:00 → STL 2027-01-21 19:10:00; layover at STL: 160 minutes.
    • WN4770: STL 2027-01-21 21:50:00 → MDW 2027-01-21 23:00:00.
  • Southwest Airlines WN1369: MDW 2027-02-04 11:45:00 → MCI 2027-02-04 13:15:00; nonstop; 90 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $249.85

  • Southwest Airlines WN294 / WN22: MCI 2027-01-21 12:10:00 → MDW 2027-01-21 17:15:00; 1 stop(s) via MKE; 305 minutes. Local airport times.
    • WN294: MCI 2027-01-21 12:10:00 → MKE 2027-01-21 13:40:00; layover at MKE: 160 minutes.
    • WN22: MKE 2027-01-21 16:20:00 → MDW 2027-01-21 17:15:00.
  • Southwest Airlines WN1369: MDW 2027-02-04 11:45:00 → MCI 2027-02-04 13:15:00; nonstop; 90 minutes. Local airport times.

More dates for this route