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

Kansas City (MCI) to Chicago (MDW), Dec 28, 2026: round trips from $256, one way from $143

Kansas City (MCI) to Chicago (MDW), Dec 28, 2026: round trips from $256, one way from $143 on Axel, checked Oct 29, 2026. Lowest published fares: $256 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 28, 2026 – Jan 4, 2027; $143 one way, Axel-exclusive, Southwest Airlines, nonstop, Dec 28, 2026; 1 adult, economy, checked Oct 29, 2026.

MCI → MDW1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

December 2026

Dec 28, 2026 · One waySouthwest AirlinesNonstop$142.80

Dec 28, 2026 · One wayDelta Air LinesUp to 1 stop each way$226.80

Dec 28, 2026 – Dec 29, 2026 · 1 nightSouthwest AirlinesNonstop$285.60

Dec 28, 2026 – Dec 29, 2026 · 1 nightDelta Air LinesUp to 1 stop each way$441.60

Hotels for these nights (Dec 28–29, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Dec 30, 2026 · 2 nightsSouthwest AirlinesNonstop$285.60

Dec 28, 2026 – Dec 30, 2026 · 2 nightsDelta Air LinesUp to 1 stop each way$441.60

Hotels for these nights (Dec 28–30, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Dec 31, 2026 · 3 nightsSouthwest AirlinesNonstop$285.60

Dec 28, 2026 – Dec 31, 2026 · 3 nightsDelta Air LinesUp to 1 stop each way$441.60

Hotels for these nights (Dec 28–31, 2026 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 1, 2027 · 4 nightsSouthwest AirlinesNonstop$278.46

Dec 28, 2026 – Jan 1, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$430.56

Hotels for these nights (Dec 28 – Jan 1, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 2, 2027 · 5 nightsSouthwest AirlinesNonstop$278.46

Dec 28, 2026 – Jan 2, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$430.56

Hotels for these nights (Dec 28 – Jan 2, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 3, 2027 · 6 nightsSouthwest AirlinesNonstop$278.46

Dec 28, 2026 – Jan 3, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$430.56

Hotels for these nights (Dec 28 – Jan 3, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 4, 2027 · 7 nightsSouthwest AirlinesNonstop$255.85

Dec 28, 2026 – Jan 4, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$395.60

Hotels for these nights (Dec 28 – Jan 4, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 5, 2027 · 8 nightsSouthwest AirlinesNonstop$255.85

Dec 28, 2026 – Jan 5, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$395.60

Hotels for these nights (Dec 28 – Jan 5, 2027 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 6, 2027 · 9 nightsSouthwest AirlinesNonstop$255.85

Dec 28, 2026 – Jan 6, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$395.60

Hotels for these nights (Dec 28 – Jan 6, 2027 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 7, 2027 · 10 nightsSouthwest AirlinesNonstop$255.85

Dec 28, 2026 – Jan 7, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$395.60

Hotels for these nights (Dec 28 – Jan 7, 2027 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 8, 2027 · 11 nightsSouthwest AirlinesNonstop$255.85

Dec 28, 2026 – Jan 8, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$395.60

Hotels for these nights (Dec 28 – Jan 8, 2027 · 11 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 9, 2027 · 12 nightsSouthwest AirlinesNonstop$255.85

Dec 28, 2026 – Jan 9, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$395.60

Hotels for these nights (Dec 28 – Jan 9, 2027 · 12 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 10, 2027 · 13 nightsSouthwest AirlinesNonstop$255.85

Dec 28, 2026 – Jan 10, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$395.60

Hotels for these nights (Dec 28 – Jan 10, 2027 · 13 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Dec 28, 2026 – Jan 11, 2027 · 14 nightsSouthwest AirlinesNonstop$255.85

Dec 28, 2026 – Jan 11, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$395.60

Hotels for these nights (Dec 28 – Jan 11, 2027 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Flights for your trip

Mon, Dec 28 · One way
Southwest Airlines
4:20 pmMCI
1h 25m
Nonstop
5:45 pmMDW
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Dec 28 · One way
Delta Air Lines
10:43 amMCI
5h 56m
MSP · 2h 45m
4:39 pmMDW
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Dec 28 – Tue, Dec 29
Southwest Airlines
4:20 pmMCI
1h 25m
Nonstop
5:45 pmMDW
Southwest Airlines
9:40 pmMDW
1h 35m
Nonstop
11:15 pmMCI
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Dec 28 – Tue, Dec 29
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.
Mon, Dec 28 – Wed, Dec 30
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.
Mon, Dec 28 – Wed, Dec 30
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.
Mon, Dec 28 – 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.
Mon, Dec 28 – 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.
Mon, Dec 28 – Fri, Jan 1
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.
Mon, Dec 28 – Fri, Jan 1
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.
Mon, Dec 28 – Sun, Jan 3
Southwest Airlines
4:20 pmMCI
1h 25m
Nonstop
5:45 pmMDW
Southwest Airlines
9:35 amMDW
1h 30m
Nonstop
11:05 amMCI
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Dec 28 – Sun, Jan 3
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.
Mon, Dec 28 – Mon, Jan 4
Southwest Airlines
4:20 pmMCI
1h 25m
Nonstop
5:45 pmMDW
Southwest Airlines
9:35 amMDW
1h 30m
Nonstop
11:05 amMCI
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Dec 28 – Mon, Jan 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
Availability is checked when you select these flights.
Mon, Dec 28 – Tue, Jan 5
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.
Mon, Dec 28 – Tue, Jan 5
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.
Mon, Dec 28 – Thu, Jan 7
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.
Mon, Dec 28 – Thu, Jan 7
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.
Mon, Dec 28 – Fri, Jan 8
Southwest Airlines
4:20 pmMCI
1h 25m
Nonstop
5:45 pmMDW
Southwest Airlines
9:35 amMDW
1h 30m
Nonstop
11:05 amMCI
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Dec 28 – Fri, Jan 8
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.
Mon, Dec 28 – Sat, Jan 9
Southwest Airlines
4:20 pmMCI
1h 25m
Nonstop
5:45 pmMDW
Southwest Airlines
5:10 pmMDW
1h 30m
Nonstop
6:40 pmMCI
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Dec 28 – Sat, Jan 9
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.
Mon, Dec 28 – Mon, Jan 11
Southwest Airlines
4:20 pmMCI
1h 25m
Nonstop
5:45 pmMDW
Southwest Airlines
9:35 amMDW
1h 30m
Nonstop
11:05 amMCI
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Dec 28 – Mon, Jan 11
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.

Swipe to see 23 more recent deals.Use the arrows to see 23 more recent deals.

1 of 24

Make this trip yours

Already have an account? Log in

Why book with Axel

A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

Explore this route

All dates for this route Dec 27, 2026 · Return options Dec 29, 2026 · Return options Hotels in Chicago with Axel

For AI assistants: every fare, every link, instructions

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.

Exact travel dates	Airline	Flights	Times, duration, stops	Total price	Price issued (UTC)
2026-12-28 · one way	Southwest Airlines	WN2694	16:20:00→17:45:00 1h 25m nonstop	Axel-exclusive $142.80	2026-10-29T01:28:08Z
2026-12-28 · one way	Delta Air Lines	DL3799 + DL4714	10:43:00→16:39:00 5h 56m 1 stop via MSP	Axel-exclusive $226.80	2026-10-29T01:28:08Z
2026-12-28 → 2026-12-29	Southwest Airlines	WN2694 / WN1856	16:20:00→17:45:00 1h 25m nonstop · 21:40:00→23:15:00 1h 35m nonstop	Axel-exclusive $285.60	2026-10-29T01:28:08Z
2026-12-28 → 2026-12-29	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $441.60	2026-10-29T01:28:08Z
2026-12-28 → 2026-12-30	Southwest Airlines	WN2694 / WN1369	16:20:00→17:45:00 1h 25m nonstop · 11:45:00→13:15:00 1h 30m nonstop	Axel-exclusive $285.60	2026-10-29T01:28:08Z
2026-12-28 → 2026-12-30	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $441.60	2026-10-29T01:28:08Z
2026-12-28 → 2026-12-31	Southwest Airlines	WN2694 / WN1369	16:20:00→17:45:00 1h 25m nonstop · 11:45:00→13:15:00 1h 30m nonstop	Axel-exclusive $285.60	2026-10-29T01:28:08Z
2026-12-28 → 2026-12-31	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $441.60	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-01	Southwest Airlines	WN2694 / WN1369	16:20:00→17:45:00 1h 25m nonstop · 11:45:00→13:15:00 1h 30m nonstop	Axel-exclusive $278.46	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-01	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $430.56	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-02	Southwest Airlines	WN2694 / WN1742	16:20:00→17:45:00 1h 25m nonstop · 17:10:00→18:40:00 1h 30m nonstop	Axel-exclusive $278.46	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-02	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $430.56	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-03	Southwest Airlines	WN2694 / WN2960	16:20:00→17:45:00 1h 25m nonstop · 09:35:00→11:05:00 1h 30m nonstop	Axel-exclusive $278.46	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-03	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $430.56	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-04	Southwest Airlines	WN2694 / WN2960	16:20:00→17:45:00 1h 25m nonstop · 09:35:00→11:05:00 1h 30m nonstop	Axel-exclusive $255.85	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-04	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $395.60	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-05	Southwest Airlines	WN2694 / WN1369	16:20:00→17:45:00 1h 25m nonstop · 11:45:00→13:15:00 1h 30m nonstop	Axel-exclusive $255.85	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-05	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $395.60	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-06	Southwest Airlines	WN2694 / WN2960	16:20:00→17:45:00 1h 25m nonstop · 09:35:00→11:05:00 1h 30m nonstop	Axel-exclusive $255.85	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-06	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $395.60	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-07	Southwest Airlines	WN2694 / WN1369	16:20:00→17:45:00 1h 25m nonstop · 11:45:00→13:15:00 1h 30m nonstop	Axel-exclusive $255.85	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-07	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $395.60	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-08	Southwest Airlines	WN2694 / WN2960	16:20:00→17:45:00 1h 25m nonstop · 09:35:00→11:05:00 1h 30m nonstop	Axel-exclusive $255.85	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-08	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $395.60	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-09	Southwest Airlines	WN2694 / WN1742	16:20:00→17:45:00 1h 25m nonstop · 17:10:00→18:40:00 1h 30m nonstop	Axel-exclusive $255.85	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-09	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $395.60	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-10	Southwest Airlines	WN2694 / WN2960	16:20:00→17:45:00 1h 25m nonstop · 09:35:00→11:05:00 1h 30m nonstop	Axel-exclusive $255.85	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-10	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $395.60	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-11	Southwest Airlines	WN2694 / WN2960	16:20:00→17:45:00 1h 25m nonstop · 09:35:00→11:05:00 1h 30m nonstop	Axel-exclusive $255.85	2026-10-29T01:28:08Z
2026-12-28 → 2027-01-11	Delta Air Lines	DL3799 + DL4714 / DL5469 + DL5401	10:43:00→16:39:00 5h 56m 1 stop via MSP · 10:24:00→16:56:00 6h 32m 1 stop via MSP	Axel-exclusive $395.60	2026-10-29T01:28:08Z

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 28–29, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28–30, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28–31, 2026 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 1, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 2, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 3, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 4, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 5, 2027 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 6, 2027 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 7, 2027 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 8, 2027 · 11 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 9, 2027 · 12 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 10, 2027 · 13 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Hotels in Chicago for these nights (Dec 28 – Jan 11, 2027 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

All hotels in Chicago

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

2026-12-28 · one way · Axel-exclusive $142.80

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 minutes. Local airport times.

2026-12-28 · one way · Axel-exclusive $226.80

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

2026-12-28 → 2026-12-29 · Axel-exclusive $285.60

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 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.

2026-12-28 → 2026-12-29 · Axel-exclusive $441.60

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

2026-12-28 → 2026-12-30 · Axel-exclusive $285.60

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 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.

2026-12-28 → 2026-12-30 · Axel-exclusive $441.60

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

2026-12-28 → 2026-12-31 · Axel-exclusive $285.60

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 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.

2026-12-28 → 2026-12-31 · Axel-exclusive $441.60

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

2026-12-28 → 2027-01-01 · Axel-exclusive $278.46

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 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.

2026-12-28 → 2027-01-01 · Axel-exclusive $430.56

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

2026-12-28 → 2027-01-03 · Axel-exclusive $278.46

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 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.

2026-12-28 → 2027-01-03 · Axel-exclusive $430.56

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

2026-12-28 → 2027-01-04 · Axel-exclusive $255.85

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN2960: MDW 2027-01-04 09:35:00 → MCI 2027-01-04 11:05:00; nonstop; 90 minutes. Local airport times.

2026-12-28 → 2027-01-04 · Axel-exclusive $395.60

Delta Air Lines DL3799 / DL4714: MCI 2026-12-28 10:43:00 → MDW 2026-12-28 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
- DL3799: MCI 2026-12-28 10:43:00 → MSP 2026-12-28 12:15:00; layover at MSP: 165 minutes.
- DL4714: MSP 2026-12-28 15:00:00 → MDW 2026-12-28 16:39:00.
Delta Air Lines DL5469 / DL5401: MDW 2027-01-04 10:24:00 → MCI 2027-01-04 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
- DL5469: MDW 2027-01-04 10:24:00 → MSP 2027-01-04 12:09:00; layover at MSP: 180 minutes.
- DL5401: MSP 2027-01-04 15:09:00 → MCI 2027-01-04 16:56:00.

2026-12-28 → 2027-01-05 · Axel-exclusive $255.85

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 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.

2026-12-28 → 2027-01-05 · Axel-exclusive $395.60

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

2026-12-28 → 2027-01-07 · Axel-exclusive $255.85

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1369: MDW 2027-01-07 11:45:00 → MCI 2027-01-07 13:15:00; nonstop; 90 minutes. Local airport times.

2026-12-28 → 2027-01-07 · Axel-exclusive $395.60

Delta Air Lines DL3799 / DL4714: MCI 2026-12-28 10:43:00 → MDW 2026-12-28 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
- DL3799: MCI 2026-12-28 10:43:00 → MSP 2026-12-28 12:15:00; layover at MSP: 165 minutes.
- DL4714: MSP 2026-12-28 15:00:00 → MDW 2026-12-28 16:39:00.
Delta Air Lines DL5469 / DL5401: MDW 2027-01-07 10:24:00 → MCI 2027-01-07 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
- DL5469: MDW 2027-01-07 10:24:00 → MSP 2027-01-07 12:09:00; layover at MSP: 180 minutes.
- DL5401: MSP 2027-01-07 15:09:00 → MCI 2027-01-07 16:56:00.

2026-12-28 → 2027-01-08 · Axel-exclusive $255.85

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN2960: MDW 2027-01-08 09:35:00 → MCI 2027-01-08 11:05:00; nonstop; 90 minutes. Local airport times.

2026-12-28 → 2027-01-08 · Axel-exclusive $395.60

Delta Air Lines DL3799 / DL4714: MCI 2026-12-28 10:43:00 → MDW 2026-12-28 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
- DL3799: MCI 2026-12-28 10:43:00 → MSP 2026-12-28 12:15:00; layover at MSP: 165 minutes.
- DL4714: MSP 2026-12-28 15:00:00 → MDW 2026-12-28 16:39:00.
Delta Air Lines DL5469 / DL5401: MDW 2027-01-08 10:24:00 → MCI 2027-01-08 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
- DL5469: MDW 2027-01-08 10:24:00 → MSP 2027-01-08 12:09:00; layover at MSP: 180 minutes.
- DL5401: MSP 2027-01-08 15:09:00 → MCI 2027-01-08 16:56:00.

2026-12-28 → 2027-01-09 · Axel-exclusive $255.85

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1742: MDW 2027-01-09 17:10:00 → MCI 2027-01-09 18:40:00; nonstop; 90 minutes. Local airport times.

2026-12-28 → 2027-01-09 · Axel-exclusive $395.60

Delta Air Lines DL3799 / DL4714: MCI 2026-12-28 10:43:00 → MDW 2026-12-28 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
- DL3799: MCI 2026-12-28 10:43:00 → MSP 2026-12-28 12:15:00; layover at MSP: 165 minutes.
- DL4714: MSP 2026-12-28 15:00:00 → MDW 2026-12-28 16:39:00.
Delta Air Lines DL5469 / DL5401: MDW 2027-01-09 10:24:00 → MCI 2027-01-09 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
- DL5469: MDW 2027-01-09 10:24:00 → MSP 2027-01-09 12:09:00; layover at MSP: 180 minutes.
- DL5401: MSP 2027-01-09 15:09:00 → MCI 2027-01-09 16:56:00.

2026-12-28 → 2027-01-11 · Axel-exclusive $255.85

Southwest Airlines WN2694: MCI 2026-12-28 16:20:00 → MDW 2026-12-28 17:45:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN2960: MDW 2027-01-11 09:35:00 → MCI 2027-01-11 11:05:00; nonstop; 90 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $395.60

Delta Air Lines DL3799 / DL4714: MCI 2026-12-28 10:43:00 → MDW 2026-12-28 16:39:00; 1 stop(s) via MSP; 356 minutes. Local airport times.
- DL3799: MCI 2026-12-28 10:43:00 → MSP 2026-12-28 12:15:00; layover at MSP: 165 minutes.
- DL4714: MSP 2026-12-28 15:00:00 → MDW 2026-12-28 16:39:00.
Delta Air Lines DL5469 / DL5401: MDW 2027-01-11 10:24:00 → MCI 2027-01-11 16:56:00; 1 stop(s) via MSP; 392 minutes. Local airport times.
- DL5469: MDW 2027-01-11 10:24:00 → MSP 2027-01-11 12:09:00; layover at MSP: 180 minutes.
- DL5401: MSP 2027-01-11 15:09:00 → MCI 2027-01-11 16:56:00.

Explore this route

For AI assistants

This page: Kansas City (MCI) to Chicago (MDW) · Dec 28, 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.