Kansas City (MCI) to Chicago (MDW), Dec 19, 2026: round trips from $284, one way from $149

Kansas City (MCI) to Chicago (MDW), Dec 19, 2026: round trips from $284, one way from $149 on Axel, checked Oct 29, 2026. Lowest published fares: $284 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 19, 2026 – Jan 1, 2027; $149 one way, Axel-exclusive, Southwest Airlines, nonstop, Dec 19, 2026; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

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 lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Dec 19–20, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $119 total · 4★ Warwick Allerton - Chicago, $120 total · 5★ Sofitel Chicago Magnificent Mile, $321 total
• Hotels in Chicago for these nights (Dec 19–21, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $195 total · 4★ Warwick Allerton - Chicago, $209 total · 5★ Sofitel Chicago Magnificent Mile, $527 total
• Hotels in Chicago for these nights (Dec 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $275 total · 4★ Warwick Allerton - Chicago, $298 total · 5★ Sofitel Chicago Magnificent Mile, $731 total
• Hotels in Chicago for these nights (Dec 19–23, 2026 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $356 total · 4★ Warwick Allerton - Chicago, $387 total · 5★ Sofitel Chicago Magnificent Mile, $937 total
• Hotels in Chicago for these nights (Dec 19–24, 2026 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey, $455 total · 4★ Warwick Allerton - Chicago, $483 total · 5★ Sofitel Chicago Magnificent Mile, $1,144 total
• Hotels in Chicago for these nights (Dec 19–25, 2026 · 6 nights · 2 adults, 1 room): 3★ Hotel Versey, $572 total · 4★ Warwick Allerton - Chicago, $579 total · 5★ Sofitel Chicago Magnificent Mile, $1,343 total
• Hotels in Chicago for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $701 total · 4★ Warwick Allerton - Chicago, $697 total · 5★ Sofitel Chicago Magnificent Mile, $1,553 total
• Hotels in Chicago for these nights (Dec 19–27, 2026 · 8 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $817 total · 4★ Warwick Allerton - Chicago, $811 total · 5★ Sofitel Chicago Magnificent Mile, $1,759 total
• Hotels in Chicago for these nights (Dec 19–28, 2026 · 9 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $911 total · 4★ Warwick Allerton - Chicago, $907 total · 5★ Sofitel Chicago Magnificent Mile, $1,969 total
• Hotels in Chicago for these nights (Dec 19–29, 2026 · 10 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $1,003 total · 4★ Warwick Allerton - Chicago, $1,003 total · 5★ Sofitel Chicago Magnificent Mile, $2,175 total
• Hotels in Chicago for these nights (Dec 19–30, 2026 · 11 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,097 total · 4★ Warwick Allerton - Chicago, $1,097 total · 5★ Sofitel Chicago Magnificent Mile, $2,382 total
• Hotels in Chicago for these nights (Dec 19–31, 2026 · 12 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,204 total · 4★ Warwick Allerton - Chicago, $1,191 total · 5★ Sofitel Chicago Magnificent Mile, $2,585 total
• Hotels in Chicago for these nights (Dec 19 – Jan 1, 2027 · 13 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $1,407 total · 4★ Warwick Allerton - Chicago, $1,394 total · 5★ Sofitel Chicago Magnificent Mile, $3,035 total
• Hotels in Chicago for these nights (Dec 19 – Jan 2, 2027 · 14 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $1,541 total · 4★ Warwick Allerton - Chicago, $1,494 total · 5★ Sofitel Chicago Magnificent Mile, $3,238 total

All hotels in Chicago

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

2026-12-19 · one way · Axel-exclusive $148.75

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.

2026-12-19 · one way · Axel-exclusive $236.25

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.

2026-12-19 → 2026-12-20 · Axel-exclusive $297.50

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN2959: MDW 2026-12-20 07:35:00 → MCI 2026-12-20 09:05:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2026-12-20 · Axel-exclusive $460.00

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-20 10:24:00 → MCI 2026-12-20 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-20 10:24:00 → MSP 2026-12-20 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-20 15:09:00 → MCI 2026-12-20 16:56:00.

2026-12-19 → 2026-12-21 · Axel-exclusive $297.50

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN2959: MDW 2026-12-21 07:35:00 → MCI 2026-12-21 09:05:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $460.00

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-21 10:24:00 → MCI 2026-12-21 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-21 10:24:00 → MSP 2026-12-21 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-21 15:09:00 → MCI 2026-12-21 16:56:00.

2026-12-19 → 2026-12-22 · Axel-exclusive $297.50

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN249: MDW 2026-12-22 15:45:00 → MCI 2026-12-22 17:15:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2026-12-22 · Axel-exclusive $460.00

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-22 10:24:00 → MCI 2026-12-22 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-22 10:24:00 → MSP 2026-12-22 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-22 15:09:00 → MCI 2026-12-22 16:56:00.

2026-12-19 → 2026-12-23 · Axel-exclusive $297.50

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN2959: MDW 2026-12-23 07:35:00 → MCI 2026-12-23 09:05:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2026-12-23 · Axel-exclusive $460.00

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-23 10:24:00 → MCI 2026-12-23 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-23 10:24:00 → MSP 2026-12-23 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-23 15:09:00 → MCI 2026-12-23 16:56:00.

2026-12-19 → 2026-12-25 · Axel-exclusive $297.50

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN2959: MDW 2026-12-25 07:35:00 → MCI 2026-12-25 09:05:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $460.00

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-25 10:24:00 → MCI 2026-12-25 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-25 10:24:00 → MSP 2026-12-25 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-25 15:09:00 → MCI 2026-12-25 16:56:00.

2026-12-19 → 2026-12-26 · Axel-exclusive $297.50

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1742: MDW 2026-12-26 17:10:00 → MCI 2026-12-26 18:40:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $460.00

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-26 10:24:00 → MCI 2026-12-26 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-26 10:24:00 → MSP 2026-12-26 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-26 15:09:00 → MCI 2026-12-26 16:56:00.

2026-12-19 → 2026-12-27 · Axel-exclusive $297.50

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN2959: MDW 2026-12-27 07:35:00 → MCI 2026-12-27 09:05:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $460.00

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-27 10:24:00 → MCI 2026-12-27 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-27 10:24:00 → MSP 2026-12-27 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-27 15:09:00 → MCI 2026-12-27 16:56:00.

2026-12-19 → 2026-12-29 · Axel-exclusive $291.55

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1856: MDW 2026-12-29 21:40:00 → MCI 2026-12-29 23:15:00; nonstop; 95 minutes. Local airport times.

2026-12-19 → 2026-12-29 · Axel-exclusive $450.80

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-29 10:24:00 → MCI 2026-12-29 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-29 10:24:00 → MSP 2026-12-29 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-29 15:09:00 → MCI 2026-12-29 16:56:00.

2026-12-19 → 2026-12-30 · Axel-exclusive $291.55

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1369: MDW 2026-12-30 11:45:00 → MCI 2026-12-30 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2026-12-30 · Axel-exclusive $450.80

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-30 10:24:00 → MCI 2026-12-30 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-30 10:24:00 → MSP 2026-12-30 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-30 15:09:00 → MCI 2026-12-30 16:56:00.

2026-12-19 → 2026-12-31 · Axel-exclusive $291.55

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 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.

2026-12-19 → 2026-12-31 · Axel-exclusive $450.80

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 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.

2026-12-19 → 2027-01-02 · Axel-exclusive $284.41

• Southwest Airlines WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1742: MDW 2027-01-02 17:10:00 → MCI 2027-01-02 18:40:00; nonstop; 90 minutes. Local airport times.

2026-12-19 → 2027-01-02 · Axel-exclusive $439.76

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-19 10:43:00 → MDW 2026-12-19 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-19 10:43:00 → MSP 2026-12-19 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-19 15:00:00 → MDW 2026-12-19 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2027-01-02 10:24:00 → MCI 2027-01-02 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2027-01-02 10:24:00 → MSP 2027-01-02 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2027-01-02 15:09:00 → MCI 2027-01-02 16:56:00.

Explore this route

• All dates for this route
• Dec 18, 2026 · Return options
• Dec 20, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Kansas City (MCI) to Chicago (MDW) · Dec 19, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. 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 lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested 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.

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