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

Kansas City (MCI) to Chicago (MDW), Dec 20–31, 2026: from $292 round trip

Kansas City (MCI) to Chicago (MDW), Dec 20–31, 2026: from $292 round trip on Axel, checked Nov 10, 2026. Lowest published fare: $292 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 20–31, 2026, 1 adult, economy, checked Nov 10, 2026.

MCI → MDW1 adulteconomyRound trip

6 flight options · 2 airlines

Nonstop flights

Sun, Dec 20 – Thu, Dec 31

Southwest Airlines
9:00 amMCI
1h 25m
Nonstop
10:25 amMDW
Southwest Airlines
11:45 amMDW
1h 30m
Nonstop
1:15 pmMCI

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Thu, Dec 31

Southwest Airlines
4:20 pmMCI
1h 25m
Nonstop
5:45 pmMDW
Southwest Airlines
11:45 amMDW
1h 30m
Nonstop
1:15 pmMCI

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sun, Dec 20 – Thu, Dec 31

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

Availability is checked when you select these flights.

Sun, Dec 20 – Thu, Dec 31

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

Availability is checked when you select these flights.

Sun, Dec 20 – Thu, Dec 31

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

Availability is checked when you select these flights.

Sun, Dec 20 – Thu, Dec 31

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

Availability is checked when you select these flights.

Hotels for these nights (Dec 20–31, 2026 · 11 nights · 2 adults, 1 room): 3★ Hotel Versey $99 a night, $1,085 for 11 nights · 4★ Warwick Allerton - Chicago $97 a night, $1,071 for 11 nights · 5★ Sofitel Chicago Magnificent Mile $206 a night, $2,264 for 11 nights

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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All dates for this routeDec 19, 2026 · Return optionsDec 21, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Kansas City (MCI) to Chicago (MDW), Dec 20–31, 2026: from $292 round trip on Axel, checked Nov 10, 2026. Lowest published fare: $292 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 20–31, 2026, 1 adult, economy, checked Nov 10, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice checked
2026-12-20 → 2026-12-31Southwest AirlinesWN2112 / WN136909:00:00→10:25:00 1h 25m nonstop · 11:45:00→13:15:00 1h 30m nonstopAxel-exclusive $291.55Nov 10, 2026
2026-12-20 → 2026-12-31Delta Air LinesDL3799 + DL4714 / DL5469 + DL540110:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSPAxel-exclusive $450.80Nov 10, 2026
2026-12-20 → 2026-12-31Southwest AirlinesWN2694 / WN136916:20:00→17:45:00 1h 25m nonstop · 11:45:00→13:15:00 1h 30m nonstopAxel-exclusive $291.55Nov 10, 2026
2026-12-20 → 2026-12-31Southwest AirlinesWN294 + WN22 / WN136912:10:00→17:15:00 5h 05m 1 stop via MKE · 11:45:00→13:15:00 1h 30m nonstopAxel-exclusive $322.80Nov 10, 2026
2026-12-20 → 2026-12-31Southwest AirlinesWN2715 + WN4770 / WN136918:05:00→23:00:00 4h 55m 1 stop via STL · 11:45:00→13:15:00 1h 30m nonstopAxel-exclusive $322.80Nov 10, 2026
2026-12-20 → 2026-12-31Southwest AirlinesWN1418 + WN2224 / WN136913:25:00→17:50:00 4h 25m 1 stop via IND · 11:45:00→13:15:00 1h 30m nonstopAxel-exclusive $322.80Nov 10, 2026

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Chicago

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

2026-12-20 → 2026-12-31 · Axel-exclusive $291.55

  • Southwest Airlines WN2112: MCI 2026-12-20 09:00:00 → MDW 2026-12-20 10:25:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1369: MDW 2026-12-31 11:45:00 → MCI 2026-12-31 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $450.80

  • Delta Air Lines DL3799 / DL4714: MCI 2026-12-20 10:43:00 → MDW 2026-12-20 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
    • DL3799: MCI 2026-12-20 10:43:00 → MSP 2026-12-20 12:15:00; layover at MSP: 165 minutes.
    • DL4714: MSP 2026-12-20 15:00:00 → MDW 2026-12-20 16:39:00.
  • Delta Air Lines DL5469 / DL5401: MDW 2026-12-31 10:24:00 → MCI 2026-12-31 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
    • DL5469: MDW 2026-12-31 10:24:00 → MSP 2026-12-31 12:09:00; layover at MSP: 180 minutes.
    • DL5401: MSP 2026-12-31 15:09:00 → MCI 2026-12-31 16:56:00.

2026-12-20 → 2026-12-31 · Axel-exclusive $291.55

  • Southwest Airlines WN2694: MCI 2026-12-20 16:20:00 → MDW 2026-12-20 17:45:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1369: MDW 2026-12-31 11:45:00 → MCI 2026-12-31 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $322.80

  • Southwest Airlines WN294 / WN22: MCI 2026-12-20 12:10:00 → MDW 2026-12-20 17:15:00; 1 stop(s) via MKE; 305 minutes. Local airport times.
    • WN294: MCI 2026-12-20 12:10:00 → MKE 2026-12-20 13:40:00; layover at MKE: 160 minutes.
    • WN22: MKE 2026-12-20 16:20:00 → MDW 2026-12-20 17:15:00.
  • Southwest Airlines WN1369: MDW 2026-12-31 11:45:00 → MCI 2026-12-31 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $322.80

  • Southwest Airlines WN2715 / WN4770: MCI 2026-12-20 18:05:00 → MDW 2026-12-20 23:00:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2715: MCI 2026-12-20 18:05:00 → STL 2026-12-20 19:10:00; layover at STL: 160 minutes.
    • WN4770: STL 2026-12-20 21:50:00 → MDW 2026-12-20 23:00:00.
  • Southwest Airlines WN1369: MDW 2026-12-31 11:45:00 → MCI 2026-12-31 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $322.80

  • Southwest Airlines WN1418 / WN2224: MCI 2026-12-20 13:25:00 → MDW 2026-12-20 17:50:00; 1 stop(s) via IND; 265 minutes. Local airport times.
    • WN1418: MCI 2026-12-20 13:25:00 → IND 2026-12-20 15:45:00; layover at IND: 115 minutes.
    • WN2224: IND 2026-12-20 17:40:00 → MDW 2026-12-20 17:50:00.
  • Southwest Airlines WN1369: MDW 2026-12-31 11:45:00 → MCI 2026-12-31 13:15:00; nonstop; 90 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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For AI assistants

  • This page: Kansas City (MCI) to Chicago (MDW) · Dec 20, 2026 · return Dec 31, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
  • Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • 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. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. 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.