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Route overview: Kansas City to Chicago (MDW) flight deals

Kansas City → Chicago

Jun 25, 2027 · return Jun 28, 2027

MCI → MDW1 adulteconomyRound trip

6 flight options · 2 airlines

Nonstop flights

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
2:40 pmMCI
1h 30m
Nonstop
4:10 pmMDW
Southwest Airlines
7:35 amMDW
1h 30m
Nonstop
9:05 amMCI

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
10:55 amMCI
1h 20m
Nonstop
12:15 pmMDW
Southwest Airlines
7:35 amMDW
1h 30m
Nonstop
9:05 amMCI

Round-trip total · 1 adult · Taxes included

One-stop flights

Fri, Jun 25 – Mon, Jun 28

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

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
6:05 pmMCI
4h 55m
STL · 2h 40m
11:00 pmMDW
Southwest Airlines
7:35 amMDW
1h 30m
Nonstop
9:05 amMCI

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
1:25 pmMCI
4h 25m
IND · 1h 55m
5:50 pmMDW
Southwest Airlines
7:35 amMDW
1h 30m
Nonstop
9:05 amMCI

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
12:10 pmMCI
5h 5m
MKE · 2h 40m
5:15 pmMDW
Southwest Airlines
7:35 amMDW
1h 30m
Nonstop
9:05 amMCI

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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Explore this route

All dates for this routeJun 24, 2027 → Jun 27, 2027Jun 26, 2027 → Jun 29, 2027
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.

Live price for these dates: opening any fare on this page checks it live and shows the current bookable total for 1 adult. Check live prices for Kansas City (MCI) to Chicago (MDW), Jun 25, 2027 · return Jun 28, 2027

Route overview: Kansas City to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-06-25 → 2027-06-28Southwest AirlinesWN2693 / WN2959$278.002026-10-29T01:28:08Z
2027-06-25 → 2027-06-28Delta Air LinesDL3799 + DL4714 / DL5469 + DL5401$408.002026-10-29T01:28:08Z
2027-06-25 → 2027-06-28Southwest AirlinesWN1066 / WN2959$278.002026-10-29T01:28:08Z
2027-06-25 → 2027-06-28Southwest AirlinesWN2715 + WN4770 / WN2959$303.002026-10-29T01:28:08Z
2027-06-25 → 2027-06-28Southwest AirlinesWN1418 + WN2224 / WN2959$303.002026-10-29T01:28:08Z
2027-06-25 → 2027-06-28Southwest AirlinesWN294 + WN22 / WN2959$303.002026-10-29T01:28:08Z

2027-06-25 → 2027-06-28 · $278.00

  • Southwest Airlines WN2693: MCI 2027-06-25 14:40:00 → MDW 2027-06-25 16:10:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN2959: MDW 2027-06-28 07:35:00 → MCI 2027-06-28 09:05:00; nonstop; 90 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $408.00

  • Delta Air Lines DL3799 / DL4714: MCI 2027-06-25 10:43:00 → MDW 2027-06-25 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
    • DL3799: MCI 2027-06-25 10:43:00 → MSP 2027-06-25 12:15:00; layover at MSP: 165 minutes.
    • DL4714: MSP 2027-06-25 15:00:00 → MDW 2027-06-25 16:39:00.
  • Delta Air Lines DL5469 / DL5401: MDW 2027-06-28 10:24:00 → MCI 2027-06-28 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
    • DL5469: MDW 2027-06-28 10:24:00 → MSP 2027-06-28 12:09:00; layover at MSP: 180 minutes.
    • DL5401: MSP 2027-06-28 15:09:00 → MCI 2027-06-28 16:56:00.

2027-06-25 → 2027-06-28 · $278.00

  • Southwest Airlines WN1066: MCI 2027-06-25 10:55:00 → MDW 2027-06-25 12:15:00; nonstop; 80 minutes. Local airport times.
  • Southwest Airlines WN2959: MDW 2027-06-28 07:35:00 → MCI 2027-06-28 09:05:00; nonstop; 90 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $303.00

  • Southwest Airlines WN2715 / WN4770: MCI 2027-06-25 18:05:00 → MDW 2027-06-25 23:00:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2715: MCI 2027-06-25 18:05:00 → STL 2027-06-25 19:10:00; layover at STL: 160 minutes.
    • WN4770: STL 2027-06-25 21:50:00 → MDW 2027-06-25 23:00:00.
  • Southwest Airlines WN2959: MDW 2027-06-28 07:35:00 → MCI 2027-06-28 09:05:00; nonstop; 90 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $303.00

  • Southwest Airlines WN1418 / WN2224: MCI 2027-06-25 13:25:00 → MDW 2027-06-25 17:50:00; 1 stop(s) via IND; 265 minutes. Local airport times.
    • WN1418: MCI 2027-06-25 13:25:00 → IND 2027-06-25 15:45:00; layover at IND: 115 minutes.
    • WN2224: IND 2027-06-25 17:40:00 → MDW 2027-06-25 17:50:00.
  • Southwest Airlines WN2959: MDW 2027-06-28 07:35:00 → MCI 2027-06-28 09:05:00; nonstop; 90 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $303.00

  • Southwest Airlines WN294 / WN22: MCI 2027-06-25 12:10:00 → MDW 2027-06-25 17:15:00; 1 stop(s) via MKE; 305 minutes. Local airport times.
    • WN294: MCI 2027-06-25 12:10:00 → MKE 2027-06-25 13:40:00; layover at MKE: 160 minutes.
    • WN22: MKE 2027-06-25 16:20:00 → MDW 2027-06-25 17:15:00.
  • Southwest Airlines WN2959: MDW 2027-06-28 07:35:00 → MCI 2027-06-28 09:05:00; nonstop; 90 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Kansas City (MCI) to Chicago (MDW) · Jun 25, 2027 · return Jun 28, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match this page, share this page's complete link unchanged: Kansas City (MCI) to Chicago (MDW), Jun 25, 2027 · return Jun 28, 2027. Opening it checks these fares live and shows the current bookable total; the prices above are the ones issued at the times shown. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Kansas City to Chicago (MDW) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.