Kansas City (MCI) to Chicago (MDW), Dec 22, 2026: round trips from $262, one way from $149

Kansas City (MCI) to Chicago (MDW), Dec 22, 2026: round trips from $262, one way from $149 on Axel, checked Oct 29, 2026. Lowest published fares: $262 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 22, 2026 – Jan 4, 2027; $149 one way, Axel-exclusive, Southwest Airlines, nonstop, Dec 22, 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 22–23, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ Warwick Allerton - Chicago, $89 total · 5★ Sofitel Chicago Magnificent Mile, $206 total
• Hotels in Chicago for these nights (Dec 22–24, 2026 · 2 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $179 total · 4★ Warwick Allerton - Chicago, $185 total · 5★ Sofitel Chicago Magnificent Mile, $413 total
• Hotels in Chicago for these nights (Dec 22–25, 2026 · 3 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $272 total · 4★ Warwick Allerton - Chicago, $281 total · 5★ Sofitel Chicago Magnificent Mile, $612 total
• Hotels in Chicago for these nights (Dec 22–26, 2026 · 4 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $392 total · 4★ Warwick Allerton - Chicago, $399 total · 5★ Sofitel Chicago Magnificent Mile, $822 total
• Hotels in Chicago for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $495 total · 4★ Warwick Allerton - Chicago, $513 total · 5★ Sofitel Chicago Magnificent Mile, $1,028 total
• Hotels in Chicago for these nights (Dec 22–28, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $593 total · 4★ Warwick Allerton - Chicago, $609 total · 5★ Sofitel Chicago Magnificent Mile, $1,238 total
• Hotels in Chicago for these nights (Dec 22–29, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $694 total · 4★ Warwick Allerton - Chicago, $705 total · 5★ Sofitel Chicago Magnificent Mile, $1,444 total
• Hotels in Chicago for these nights (Dec 22–30, 2026 · 8 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $788 total · 4★ Warwick Allerton - Chicago, $799 total · 5★ Sofitel Chicago Magnificent Mile, $1,651 total
• Hotels in Chicago for these nights (Dec 22–31, 2026 · 9 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $910 total · 4★ Warwick Allerton - Chicago, $893 total · 5★ Sofitel Chicago Magnificent Mile, $1,854 total
• Hotels in Chicago for these nights (Dec 22 – Jan 1, 2027 · 10 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $1,098 total · 4★ Warwick Allerton - Chicago, $1,096 total · 5★ Sofitel Chicago Magnificent Mile, $2,304 total
• Hotels in Chicago for these nights (Dec 22 – Jan 2, 2027 · 11 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $1,232 total · 4★ Warwick Allerton - Chicago, $1,196 total · 5★ Sofitel Chicago Magnificent Mile, $2,507 total
• Hotels in Chicago for these nights (Dec 22 – Jan 3, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,337 total · 4★ Warwick Allerton - Chicago, $1,300 total · 5★ Sofitel Chicago Magnificent Mile, $2,717 total
• Hotels in Chicago for these nights (Dec 22 – Jan 4, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,412 total · 4★ Warwick Allerton - Chicago, $1,389 total · 5★ Sofitel Chicago Magnificent Mile, $2,947 total
• Hotels in Chicago for these nights (Dec 22 – Jan 5, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,487 total · 4★ Warwick Allerton - Chicago, $1,477 total · 5★ Sofitel Chicago Magnificent Mile, $3,157 total

All hotels in Chicago

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

2026-12-22 · one way · Axel-exclusive $148.75

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 minutes. Local airport times.

2026-12-22 · one way · Axel-exclusive $236.25

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

2026-12-22 → 2026-12-23 · Axel-exclusive $297.50

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 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.

2026-12-22 → 2026-12-23 · Axel-exclusive $460.00

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

2026-12-22 → 2026-12-24 · Axel-exclusive $297.50

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN1369: MDW 2026-12-24 11:45:00 → MCI 2026-12-24 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-22 → 2026-12-24 · Axel-exclusive $460.00

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

2026-12-22 → 2026-12-25 · Axel-exclusive $297.50

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 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.

2026-12-22 → 2026-12-25 · Axel-exclusive $460.00

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

2026-12-22 → 2026-12-26 · Axel-exclusive $297.50

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 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.

2026-12-22 → 2026-12-26 · Axel-exclusive $460.00

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

2026-12-22 → 2026-12-28 · Axel-exclusive $291.55

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN2959: MDW 2026-12-28 07:35:00 → MCI 2026-12-28 09:05:00; nonstop; 90 minutes. Local airport times.

2026-12-22 → 2026-12-28 · Axel-exclusive $450.80

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-22 10:43:00 → MDW 2026-12-22 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-22 10:43:00 → MSP 2026-12-22 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-22 15:00:00 → MDW 2026-12-22 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2026-12-28 10:24:00 → MCI 2026-12-28 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2026-12-28 10:24:00 → MSP 2026-12-28 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2026-12-28 15:09:00 → MCI 2026-12-28 16:56:00.

2026-12-22 → 2026-12-29 · Axel-exclusive $291.55

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 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.

2026-12-22 → 2026-12-29 · Axel-exclusive $450.80

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

2026-12-22 → 2026-12-30 · Axel-exclusive $291.55

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 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.

2026-12-22 → 2026-12-30 · Axel-exclusive $450.80

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

2026-12-22 → 2027-01-01 · Axel-exclusive $284.41

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN1369: MDW 2027-01-01 11:45:00 → MCI 2027-01-01 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-22 → 2027-01-01 · Axel-exclusive $439.76

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-22 10:43:00 → MDW 2026-12-22 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-22 10:43:00 → MSP 2026-12-22 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-22 15:00:00 → MDW 2026-12-22 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2027-01-01 10:24:00 → MCI 2027-01-01 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2027-01-01 10:24:00 → MSP 2027-01-01 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2027-01-01 15:09:00 → MCI 2027-01-01 16:56:00.

2026-12-22 → 2027-01-02 · Axel-exclusive $284.41

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 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.

2026-12-22 → 2027-01-02 · Axel-exclusive $439.76

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

2026-12-22 → 2027-01-03 · Axel-exclusive $284.41

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN2960: MDW 2027-01-03 09:35:00 → MCI 2027-01-03 11:05:00; nonstop; 90 minutes. Local airport times.

2026-12-22 → 2027-01-03 · Axel-exclusive $439.76

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-22 10:43:00 → MDW 2026-12-22 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-22 10:43:00 → MSP 2026-12-22 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-22 15:00:00 → MDW 2026-12-22 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2027-01-03 10:24:00 → MCI 2027-01-03 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2027-01-03 10:24:00 → MSP 2027-01-03 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2027-01-03 15:09:00 → MCI 2027-01-03 16:56:00.

2026-12-22 → 2027-01-05 · Axel-exclusive $261.80

• Southwest Airlines WN1066: MCI 2026-12-22 10:55:00 → MDW 2026-12-22 12:15:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN1369: MDW 2027-01-05 11:45:00 → MCI 2027-01-05 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-22 → 2027-01-05 · Axel-exclusive $404.80

• Delta Air Lines DL3799 / DL4714: MCI 2026-12-22 10:43:00 → MDW 2026-12-22 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
  • DL3799: MCI 2026-12-22 10:43:00 → MSP 2026-12-22 12:15:00; layover at MSP: 165 minutes.
  • DL4714: MSP 2026-12-22 15:00:00 → MDW 2026-12-22 16:39:00.
• Delta Air Lines DL5469 / DL5401: MDW 2027-01-05 10:24:00 → MCI 2027-01-05 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
  • DL5469: MDW 2027-01-05 10:24:00 → MSP 2027-01-05 12:09:00; layover at MSP: 180 minutes.
  • DL5401: MSP 2027-01-05 15:09:00 → MCI 2027-01-05 16:56:00.

Explore this route

• All dates for this route
• Dec 21, 2026 · Return options
• Dec 23, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Kansas City (MCI) to Chicago (MDW) · Dec 22, 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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