# Chicago (MDW) to Kahului (OGG)

Lowest published fares for the months ahead: $600 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 3–6, 2026; $325 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 1, 2026; 73 priced flights on 73 exact dates, 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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### Chicago (MDW) to Kahului (OGG): November 2026

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · [Compare return dates departing Nov 20, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/nov-20) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $675](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/november-20-2026/return/november-23-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-11-20.WN.1.WN2691-WN1593.LAS%7EOGG-MDW.2026-11-23.WN.1.WN3263-WN3895.SJC) |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · [Compare return dates departing Nov 21, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/nov-21) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $750](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/november-21-2026/return/november-28-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-11-21.WN.1.WN3020-WN3157.SAN%7EOGG-MDW.2026-11-28.WN.1.WN3263-WN3895.SJC) |
| Nov 24, 2026 · One way · [Compare return dates departing Nov 24, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/nov-24) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $406](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/november-24-2026/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2026-11-24.WN.1.WN3020-WN3157.SAN) |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · [Compare return dates departing Nov 24, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/nov-24) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $750](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/november-24-2026/return/november-29-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-11-24.WN.1.WN3020-WN3157.SAN%7EOGG-MDW.2026-11-29.WN.1.WN3261-WN3443.PHX) |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · [Compare return dates departing Nov 26, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/nov-26) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $750](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/november-26-2026/return/november-29-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-11-26.WN.1.WN3020-WN3157.SAN%7EOGG-MDW.2026-11-29.WN.1.WN3261-WN3443.PHX) |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · [Compare return dates departing Nov 27, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/nov-27) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $675](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/november-27-2026/return/november-30-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-11-27.WN.1.WN3020-WN3157.SAN%7EOGG-MDW.2026-11-30.WN.1.WN3263-WN3895.SJC) |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · [Compare return dates departing Nov 28, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/nov-28) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $675](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/november-28-2026/return/december-5-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-11-28.WN.1.WN3020-WN3157.SAN%7EOGG-MDW.2026-12-05.WN.1.WN3263-WN3895.SJC) |

### Chicago (MDW) to Kahului (OGG): December 2026

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Dec 1, 2026 · One way · [Compare return dates departing Dec 1, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-1) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-1-2026/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-01.WN.1.WN3020-WN3157.SAN) |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · [Compare return dates departing Dec 3, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-3) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-3-2026/return/december-6-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-03.WN.1.WN3020-WN3157.SAN%7EOGG-MDW.2026-12-06.WN.1.WN3261-WN3443.PHX) |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · [Compare return dates departing Dec 4, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-4) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-4-2026/return/december-7-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-04.WN.1.WN3020-WN3157.SAN%7EOGG-MDW.2026-12-07.WN.1.WN3261-WN3443.PHX) |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · [Compare return dates departing Dec 5, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-5) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-5-2026/return/december-12-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-05.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-12.WN.1.WN3261-WN3443.PHX) |
| Dec 8, 2026 · One way · [Compare return dates departing Dec 8, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-8) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-8-2026/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-08.WN.1.WN2995-WN2618.PHX) |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · [Compare return dates departing Dec 10, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-10) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-10-2026/return/december-13-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-10.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-13.WN.1.WN3261-WN3443.PHX) |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · [Compare return dates departing Dec 11, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-11) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-11-2026/return/december-14-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-11.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-14.WN.1.WN3261-WN3443.PHX) |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · [Compare return dates departing Dec 12, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-12) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $735](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-12-2026/return/december-19-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-12.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-19.WN.1.WN3261-WN3443.PHX) |
| Dec 15, 2026 · One way · [Compare return dates departing Dec 15, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-15) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-15-2026/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-15.WN.1.WN2995-WN2618.PHX) |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · [Compare return dates departing Dec 17, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-17) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $735](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-17-2026/return/december-20-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-17.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-20.WN.1.WN3261-WN3443.PHX) |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · [Compare return dates departing Dec 18, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-18) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $735](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-18-2026/return/december-21-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-18.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-21.WN.1.WN3261-WN3443.PHX) |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · [Compare return dates departing Dec 19, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-19) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $870](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-19-2026/return/december-26-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-19.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-26.WN.1.WN3261-WN3443.PHX) |
| Dec 22, 2026 · One way · [Compare return dates departing Dec 22, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-22) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $471](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-22-2026/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-22.WN.1.WN2995-WN2618.PHX) |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · [Compare return dates departing Dec 22, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-22) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $870](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-22-2026/return/december-27-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-22.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-27.WN.1.WN3261-WN3443.PHX) |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · [Compare return dates departing Dec 24, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-24) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $870](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-24-2026/return/december-27-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-24.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-27.WN.1.WN3261-WN3443.PHX) |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · [Compare return dates departing Dec 25, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-25) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $870](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-25-2026/return/december-28-2026/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-25.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2026-12-28.WN.1.WN3261-WN3443.PHX) |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · [Compare return dates departing Dec 26, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-26) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $870](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-26-2026/return/january-2-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-26.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-02.WN.1.WN3261-WN3443.PHX) |
| Dec 29, 2026 · One way · [Compare return dates departing Dec 29, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-29) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $471](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-29-2026/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-29.WN.1.WN2995-WN2618.PHX) |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · [Compare return dates departing Dec 30, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-30) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $870](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-30-2026/return/january-2-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-30.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-02.WN.1.WN3261-WN3443.PHX) |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · [Compare return dates departing Dec 31, 2026](https://helloaxel.com/en/flights/choose/mdw-ogg/dec-31) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $870](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/december-31-2026/return/january-3-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2026-12-31.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-03.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): January 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · [Compare return dates departing Jan 1, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-1) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $735](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-1-2027/return/january-4-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-01.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-04.WN.1.WN3261-WN3443.PHX) |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · [Compare return dates departing Jan 2, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-2) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $735](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-2-2027/return/january-9-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-02.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-09.WN.1.WN3261-WN3443.PHX) |
| Jan 5, 2027 · One way · [Compare return dates departing Jan 5, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-5) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-5-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-05.WN.1.WN2995-WN2618.PHX) |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · [Compare return dates departing Jan 7, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-7) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-7-2027/return/january-10-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-07.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-10.WN.1.WN3261-WN3443.PHX) |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · [Compare return dates departing Jan 8, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-8) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-8-2027/return/january-11-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-08.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-11.WN.1.WN3261-WN3443.PHX) |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · [Compare return dates departing Jan 9, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-9) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-9-2027/return/january-16-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-09.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-16.WN.1.WN3261-WN3443.PHX) |
| Jan 12, 2027 · One way · [Compare return dates departing Jan 12, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-12) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-12-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-12.WN.1.WN2995-WN2618.PHX) |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · [Compare return dates departing Jan 14, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-14) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-14-2027/return/january-17-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-14.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-17.WN.1.WN3261-WN3443.PHX) |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · [Compare return dates departing Jan 15, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-15) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-15-2027/return/january-18-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-15.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-18.WN.1.WN3261-WN3443.PHX) |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · [Compare return dates departing Jan 16, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-16) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-16-2027/return/january-23-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-16.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-23.WN.1.WN3261-WN3443.PHX) |
| Jan 19, 2027 · One way · [Compare return dates departing Jan 19, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-19) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-19-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-19.WN.1.WN2995-WN2618.PHX) |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · [Compare return dates departing Jan 21, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-21) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-21-2027/return/january-24-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-21.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-24.WN.1.WN3261-WN3443.PHX) |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · [Compare return dates departing Jan 22, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-22) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-22-2027/return/january-25-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-22.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-25.WN.1.WN3261-WN3443.PHX) |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · [Compare return dates departing Jan 23, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-23) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-23-2027/return/january-30-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-23.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-30.WN.1.WN3261-WN3443.PHX) |
| Jan 26, 2027 · One way · [Compare return dates departing Jan 26, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-26) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-26-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-26.WN.1.WN2995-WN2618.PHX) |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · [Compare return dates departing Jan 28, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-28) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-28-2027/return/january-31-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-28.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-01-31.WN.1.WN3261-WN3443.PHX) |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · [Compare return dates departing Jan 29, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-29) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-29-2027/return/february-1-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-29.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-02-01.WN.1.WN3261-WN3443.PHX) |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · [Compare return dates departing Jan 30, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jan-30) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/january-30-2027/return/february-6-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-01-30.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-02-06.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): February 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Feb 2, 2027 · One way · [Compare return dates departing Feb 2, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/feb-2) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/february-2-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2027-02-02.WN.1.WN2995-WN2618.PHX) |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · [Compare return dates departing Feb 4, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/feb-4) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/february-4-2027/return/february-7-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-02-04.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-02-07.WN.1.WN3261-WN3443.PHX) |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · [Compare return dates departing Feb 5, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/feb-5) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/february-5-2027/return/february-8-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-02-05.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-02-08.WN.1.WN3261-WN3443.PHX) |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · [Compare return dates departing Feb 6, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/feb-6) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $645](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/february-6-2027/return/february-13-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-02-06.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-02-13.WN.1.WN3261-WN3443.PHX) |
| Feb 9, 2027 · One way · [Compare return dates departing Feb 9, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/feb-9) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $325](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/february-9-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-OGG.2027-02-09.WN.1.WN2995-WN2618.PHX) |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · [Compare return dates departing Feb 12, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/feb-12) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $690](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/february-12-2027/return/february-15-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-02-12.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-02-15.WN.1.WN3261-WN3443.PHX) |
| Feb 26, 2027 – Mar 1, 2027 · 3 nights · [Compare return dates departing Feb 26, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/feb-26) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/february-26-2027/return/march-1-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-02-26.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-03-01.WN.1.WN3261-WN3443.PHX) |
| Feb 27, 2027 – Mar 6, 2027 · 7 nights · [Compare return dates departing Feb 27, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/feb-27) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $600](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/february-27-2027/return/march-6-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-02-27.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-03-06.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): March 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · [Compare return dates departing Mar 25, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/mar-25) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $800](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/march-25-2027/return/march-29-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-03-25.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-03-29.WN.1.WN3261-WN3443.PHX) |
| Mar 26, 2027 – Mar 29, 2027 · 3 nights · [Compare return dates departing Mar 26, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/mar-26) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $800](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/march-26-2027/return/march-29-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-03-26.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-03-29.WN.1.WN3261-WN3443.PHX) |
| Mar 27, 2027 – Apr 3, 2027 · 7 nights · [Compare return dates departing Mar 27, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/mar-27) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $698](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/march-27-2027/return/april-3-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-03-27.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-04-03.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): April 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Apr 23, 2027 – Apr 26, 2027 · 3 nights · [Compare return dates departing Apr 23, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/apr-23) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $646](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/april-23-2027/return/april-26-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-04-23.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-04-26.WN.1.WN3261-WN3443.PHX) |
| Apr 24, 2027 – May 1, 2027 · 7 nights · [Compare return dates departing Apr 24, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/apr-24) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $646](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/april-24-2027/return/may-1-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-04-24.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-05-01.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): May 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| May 21, 2027 – May 24, 2027 · 3 nights · [Compare return dates departing May 21, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/may-21) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $646](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/may-21-2027/return/may-24-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-05-21.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-05-24.WN.1.WN3261-WN3443.PHX) |
| May 22, 2027 – May 29, 2027 · 7 nights · [Compare return dates departing May 22, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/may-22) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $694](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/may-22-2027/return/may-29-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-05-22.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-05-29.WN.1.WN3261-WN3443.PHX) |
| May 28, 2027 – May 31, 2027 · 3 nights · [Compare return dates departing May 28, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/may-28) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $741](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/may-28-2027/return/may-31-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-05-28.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-05-31.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): June 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Jun 18, 2027 – Jun 21, 2027 · 3 nights · [Compare return dates departing Jun 18, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jun-18) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $680](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/june-18-2027/return/june-21-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-06-18.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-06-21.WN.1.WN3261-WN3443.PHX) |
| Jun 19, 2027 – Jun 26, 2027 · 7 nights · [Compare return dates departing Jun 19, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jun-19) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $680](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/june-19-2027/return/june-26-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-06-19.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-06-26.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): July 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · [Compare return dates departing Jul 2, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jul-2) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $782](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/july-2-2027/return/july-6-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-07-02.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-07-06.WN.1.WN3261-WN3443.PHX) |
| Jul 16, 2027 – Jul 19, 2027 · 3 nights · [Compare return dates departing Jul 16, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jul-16) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $680](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/july-16-2027/return/july-19-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-07-16.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-07-19.WN.1.WN3261-WN3443.PHX) |
| Jul 17, 2027 – Jul 24, 2027 · 7 nights · [Compare return dates departing Jul 17, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/jul-17) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $680](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/july-17-2027/return/july-24-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-07-17.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-07-24.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): August 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Aug 13, 2027 – Aug 16, 2027 · 3 nights · [Compare return dates departing Aug 13, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/aug-13) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $680](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/august-13-2027/return/august-16-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-08-13.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-08-16.WN.1.WN3261-WN3443.PHX) |
| Aug 14, 2027 – Aug 21, 2027 · 7 nights · [Compare return dates departing Aug 14, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/aug-14) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $680](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/august-14-2027/return/august-21-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-08-14.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-08-21.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): September 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · [Compare return dates departing Sep 3, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/sep-3) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $734](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/september-3-2027/return/september-6-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-09-03.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-09-06.WN.1.WN3261-WN3443.PHX) |
| Sep 10, 2027 – Sep 13, 2027 · 3 nights · [Compare return dates departing Sep 10, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/sep-10) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $612](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/september-10-2027/return/september-13-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-09-10.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-09-13.WN.1.WN3261-WN3443.PHX) |
| Sep 11, 2027 – Sep 18, 2027 · 7 nights · [Compare return dates departing Sep 11, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/sep-11) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $612](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/september-11-2027/return/september-18-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-09-11.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-09-18.WN.1.WN3261-WN3443.PHX) |

### Chicago (MDW) to Kahului (OGG): October 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Oct 1, 2027 – Oct 4, 2027 · 3 nights · [Compare return dates departing Oct 1, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/oct-1) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $646](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/october-1-2027/return/october-4-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-10-01.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-10-04.WN.1.WN3261-WN3443.PHX) |
| Oct 2, 2027 – Oct 9, 2027 · 7 nights · [Compare return dates departing Oct 2, 2027](https://helloaxel.com/en/flights/choose/mdw-ogg/oct-2) | Southwest Airlines | Up to 1 stop each way | [Axel-exclusive $646](https://helloaxel.com/en/f/start/from/mdw/to/ogg/depart/october-2-2027/return/october-9-2027/adults/1/cabin/economy?example_flight=MDW-OGG.2027-10-02.WN.1.WN2995-WN2618.PHX%7EOGG-MDW.2027-10-09.WN.1.WN3261-WN3443.PHX) |

[Route overview: Chicago to Kahului (OGG) flight deals](/en/flights/from-chicago-to-kahului-ogg)

### 2026-11-20 → 2026-11-23 · Axel-exclusive $675

- Southwest Airlines WN2691 / WN1593: MDW 2026-11-20 05:50:00 → OGG 2026-11-20 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  - WN2691: MDW 2026-11-20 05:50:00 → LAS 2026-11-20 07:45:00; layover at LAS: 75 minutes.
  - WN1593: LAS 2026-11-20 09:00:00 → OGG 2026-11-20 13:10:00.
- Southwest Airlines WN3263 / WN3895: OGG 2026-11-23 14:25:00 → MDW 2026-11-24 05:00:00; 1 stop(s) via SJC; 635 minutes. Local airport times.
  - WN3263: OGG 2026-11-23 14:25:00 → SJC 2026-11-23 21:25:00; layover at SJC: 95 minutes.
  - WN3895: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00.

### 2026-11-24 · one way · Axel-exclusive $406

- Southwest Airlines WN3020 / WN3157: MDW 2026-11-24 06:00:00 → OGG 2026-11-24 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  - WN3020: MDW 2026-11-24 06:00:00 → SAN 2026-11-24 08:30:00; layover at SAN: 145 minutes.
  - WN3157: SAN 2026-11-24 10:55:00 → OGG 2026-11-24 14:40:00.

### 2026-12-03 → 2026-12-06 · Axel-exclusive $600

- Southwest Airlines WN3020 / WN3157: MDW 2026-12-03 06:00:00 → OGG 2026-12-03 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  - WN3020: MDW 2026-12-03 06:00:00 → SAN 2026-12-03 08:30:00; layover at SAN: 145 minutes.
  - WN3157: SAN 2026-12-03 10:55:00 → OGG 2026-12-03 14:40:00.
- Southwest Airlines WN3261 / WN3443: OGG 2026-12-06 20:15:00 → MDW 2026-12-07 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2026-12-06 20:15:00 → PHX 2026-12-07 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2026-12-07 08:20:00 → MDW 2026-12-07 12:35:00.

### 2026-12-17 → 2026-12-20 · Axel-exclusive $735

- Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2026-12-20 20:15:00 → MDW 2026-12-21 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2026-12-20 20:15:00 → PHX 2026-12-21 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2026-12-21 08:20:00 → MDW 2026-12-21 12:35:00.

### 2026-12-26 → 2027-01-02 · Axel-exclusive $870

- Southwest Airlines WN2995 / WN2618: MDW 2026-12-26 05:20:00 → OGG 2026-12-26 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2026-12-26 05:20:00 → PHX 2026-12-26 08:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2026-12-26 09:30:00 → OGG 2026-12-26 12:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2027-01-02 20:15:00 → MDW 2027-01-03 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2027-01-02 20:15:00 → PHX 2027-01-03 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2027-01-03 08:20:00 → MDW 2027-01-03 12:35:00.

### 2027-01-08 → 2027-01-11 · Axel-exclusive $600

- Southwest Airlines WN2995 / WN2618: MDW 2027-01-08 05:20:00 → OGG 2027-01-08 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2027-01-08 05:20:00 → PHX 2027-01-08 08:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2027-01-08 09:30:00 → OGG 2027-01-08 12:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2027-01-11 20:15:00 → MDW 2027-01-12 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2027-01-11 20:15:00 → PHX 2027-01-12 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2027-01-12 08:20:00 → MDW 2027-01-12 12:35:00.

### 2027-01-22 → 2027-01-25 · Axel-exclusive $600

- Southwest Airlines WN2995 / WN2618: MDW 2027-01-22 05:20:00 → OGG 2027-01-22 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2027-01-22 05:20:00 → PHX 2027-01-22 08:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2027-01-22 09:30:00 → OGG 2027-01-22 12:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2027-01-25 20:15:00 → MDW 2027-01-26 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2027-01-25 20:15:00 → PHX 2027-01-26 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2027-01-26 08:20:00 → MDW 2027-01-26 12:35:00.

### 2027-02-05 → 2027-02-08 · Axel-exclusive $600

- Southwest Airlines WN2995 / WN2618: MDW 2027-02-05 05:20:00 → OGG 2027-02-05 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2027-02-05 05:20:00 → PHX 2027-02-05 08:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2027-02-05 09:30:00 → OGG 2027-02-05 12:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2027-02-08 20:15:00 → MDW 2027-02-09 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2027-02-08 20:15:00 → PHX 2027-02-09 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2027-02-09 08:20:00 → MDW 2027-02-09 12:35:00.

### 2027-03-26 → 2027-03-29 · Axel-exclusive $800

- Southwest Airlines WN2995 / WN2618: MDW 2027-03-26 05:20:00 → OGG 2027-03-26 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2027-03-26 05:20:00 → PHX 2027-03-26 07:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2027-03-26 08:30:00 → OGG 2027-03-26 11:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2027-03-29 20:15:00 → MDW 2027-03-30 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2027-03-29 20:15:00 → PHX 2027-03-30 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2027-03-30 08:20:00 → MDW 2027-03-30 13:35:00.

### 2027-05-28 → 2027-05-31 · Axel-exclusive $741

- Southwest Airlines WN2995 / WN2618: MDW 2027-05-28 05:20:00 → OGG 2027-05-28 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2027-05-28 05:20:00 → PHX 2027-05-28 07:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2027-05-28 08:30:00 → OGG 2027-05-28 11:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2027-05-31 20:15:00 → MDW 2027-06-01 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2027-05-31 20:15:00 → PHX 2027-06-01 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2027-06-01 08:20:00 → MDW 2027-06-01 13:35:00.

### 2027-08-13 → 2027-08-16 · Axel-exclusive $680

- Southwest Airlines WN2995 / WN2618: MDW 2027-08-13 05:20:00 → OGG 2027-08-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2027-08-13 05:20:00 → PHX 2027-08-13 07:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2027-08-13 08:30:00 → OGG 2027-08-13 11:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2027-08-16 20:15:00 → MDW 2027-08-17 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2027-08-16 20:15:00 → PHX 2027-08-17 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2027-08-17 08:20:00 → MDW 2027-08-17 13:35:00.

### 2027-10-02 → 2027-10-09 · Axel-exclusive $646

- Southwest Airlines WN2995 / WN2618: MDW 2027-10-02 05:20:00 → OGG 2027-10-02 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  - WN2995: MDW 2027-10-02 05:20:00 → PHX 2027-10-02 07:10:00; layover at PHX: 80 minutes.
  - WN2618: PHX 2027-10-02 08:30:00 → OGG 2027-10-02 11:55:00.
- Southwest Airlines WN3261 / WN3443: OGG 2027-10-09 20:15:00 → MDW 2027-10-10 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  - WN3261: OGG 2027-10-09 20:15:00 → PHX 2027-10-10 05:05:00; layover at PHX: 195 minutes.
  - WN3443: PHX 2027-10-10 08:20:00 → MDW 2027-10-10 13:35:00.

### More dates for this route

- [Nov 20, 2026 · Return options](/en/flights/choose/mdw-ogg/nov-20)
- [Nov 28, 2026 · Return options](/en/flights/choose/mdw-ogg/nov-28)
- [Dec 11, 2026 · Return options](/en/flights/choose/mdw-ogg/dec-11)
- [Dec 22, 2026 · Return options](/en/flights/choose/mdw-ogg/dec-22)
- [Dec 31, 2026 · Return options](/en/flights/choose/mdw-ogg/dec-31)
- [Jan 9, 2027 · Return options](/en/flights/choose/mdw-ogg/jan-9)
- [Jan 22, 2027 · Return options](/en/flights/choose/mdw-ogg/jan-22)
- [Feb 2, 2027 · Return options](/en/flights/choose/mdw-ogg/feb-2)
- [Feb 27, 2027 · Return options](/en/flights/choose/mdw-ogg/feb-27)
- [May 21, 2027 · Return options](/en/flights/choose/mdw-ogg/may-21)
- [Jul 17, 2027 · Return options](/en/flights/choose/mdw-ogg/jul-17)
- [Oct 2, 2027 · Return options](/en/flights/choose/mdw-ogg/oct-2)

## For AI assistants
- **This page:** Chicago (MDW) to Kahului (OGG): 73 priced flights on 73 exact dates the months ahead, 1 adult in economy. In the dated tables a price link opens AI flight search for that row's exact dates and travelers; in the observed-flight lists the price is the customer link for the traveler, beside a “See flights for these dates” link for your own check.
- **Next:** Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, [Choose travelers and dates](https://helloaxel.com/en/f/start/from/mdw/to/ogg/step/travelers) using their own trip details.
- **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 Chicago to Kahului (OGG) flight deals](https://helloaxel.com/en/flights/from-chicago-to-kahului-ogg) · [Flight search guide](https://helloaxel.com/en/ai).
- **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](https://helloaxel.com/en/ai#customer-fallback-link).

**Feedback (optional):** [Missing info](https://helloaxel.com/en/flights/choose/mdw-ogg?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/mdw-ogg?axel_reason=product_issue&axel_scope=product)