$216+ Cheap flights from Hawaii to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Jan 17 — Jan 241
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Hawaii to Midway
Cheapest flights from Hawaii to MidwayExplore the most affordable flight options available from Hawaii to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.
Explore the most affordable flight options available from Hawaii to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:00 amHNL - MDW
1 stop12h 55mSouthwest
Sun 1/118:35 pmMDW - HNL
1 stop18h 40mSouthwest
Deal found 12/17![Southwest logo]()
$630
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:00 pmHNL - MDW
1 stop11h 15mSouthwest
Mon 1/55:30 amMDW - HNL
1 stop12h 55mSouthwest
Deal found 12/15![Southwest logo]()
$733
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:00 amHNL - MDW
1 stop10h 55mSouthwest
Sun 1/410:15 pmMDW - HNL
1 stop17h 05mSouthwest
Deal found 12/15![Southwest logo]()
$795
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:35 pmOGG - MDW
1 stop11h 30mSouthwest
Sun 12/215:40 amMDW - OGG
1 stop11h 45mSouthwest
Deal found 12/17![Southwest logo]()
$859
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:15 pmKOA - MDW
1 stop12h 25mSouthwest
Mon 12/295:10 amMDW - KOA
1 stop12h 30mSouthwest
Deal found 12/16![Southwest logo]()
$1,023
This Kiwi.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:00 amHNL - MDW
2 stops33h 58mMultiple Airlines
Sun 1/43:01 pmMDW - HNL
1 stop23h 54mMultiple Airlines
Deal found 12/15![Multiple Airlines logo]()
$1,054
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:55 pmKOA - MDW
2 stops14h 24mDelta
Sun 1/49:29 amMDW - KOA
2 stops14h 06mDelta
Deal found 12/16![Delta logo]()
$1,204
This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/171:55 pmOGG - MDW
2 stops15h 24mDelta
Mon 12/226:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 12/17![Delta logo]()
$1,251
This Delta deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:20 pmHNL - MDW
2 stops16h 46mDelta
Sun 1/49:29 amMDW - HNL
2 stops16h 15mDelta
Deal found 12/15![Delta logo]()
$1,290
Find flight deals from Hawaii to Midway
Keep the following information in mind while searching for Hawaii to Midway flight deals. Data was last updated December 18, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $429 (Delta) |
One-way from | $216 (Kiwi.com) |
Popular in | July |
Cheapest in | September |
Average price | $741 |
Cheapflights Fare Finder
Customize your flight search to find flights from Hawaii to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Hawaii to Chicago Midway Airport that are best for you.
Fly from
Hawaii
Fly to
Midway
Route
Depart
Return
Price
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Wed 1/28
1:55 pm-9:08 am
2 stops15h 13m
Chicago Midway
Wed 2/4
9:32 am-9:28 pm
2 stops15h 56m
$434
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Thu 1/15
5:15 pm-9:08 am
1 stop11h 53m
Chicago Midway
Thu 1/22
9:32 am-9:28 pm
2 stops15h 56m
$465
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Wed 1/14
5:15 pm-12:48 pm
2 stops15h 33m
Chicago Midway
Thu 1/22
9:32 am-9:28 pm
2 stops15h 56m
$498
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Wed 1/28
9:55 pm-12:35 pm
1 stop10h 40m
Chicago Midway
Wed 2/4
8:55 pm-11:15 am
1 stop18h 20m
$499
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Sun 2/1
5:15 pm-9:08 am
1 stop11h 53m
Chicago Midway
Thu 2/5
9:33 am-9:28 pm
2 stops15h 55m
$528
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Sun 2/1
9:55 pm-12:35 pm
1 stop10h 40m
Chicago Midway
Thu 2/5
8:35 pm-11:15 am
1 stop18h 40m
$564
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Fri 2/20
4:45 pm-8:53 am
1 stop12h 08m
Chicago Midway
Tue 3/3
9:34 am-9:28 pm
2 stops15h 54m
$579
LihueChicago
LIH - MDW
LIHMDW
Lihue
Fri 2/6
10:35 pm-10:22 pm
2 stops19h 47m
Chicago Midway
Mon 2/9
9:33 am-7:54 pm
2 stops14h 21m
$592
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Sat 2/28
12:45 pm-5:05 am
2 stops12h 20m
Chicago Midway
Sun 3/8
7:10 am-4:35 pm
2 stops14h 25m
$682
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Sat 2/28
1:53 pm-8:53 am
2 stops15h 00m
Chicago Midway
Sun 3/8
10:49 am-6:40 pm
1 stop12h 51m
$715
Showing 1-10 of 43 results
Best time to book a flight from Hawaii to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Hawaii with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Hawaii to Chicago Midway Airport
What is the cheapest time of day to fly from HI to MDW?
Find hourly flight availability from Hawaii to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.
One of the essential ways to save on airfare from Hawaii to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 39% on airfare.
Related info for your journey
Find useful and relevant information for your journey from Hawaii to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for Hawaii to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Hawaii to Midway
Discover the top airline that operate flights from Hawaii to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$581 | Average$788 | FlexibilityNo cancel fee | On-time63% |