HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$180+ Cheap flights from O'ahu 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'ahu to Midway with Cheapflights

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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 O'ahu to Midway

Keep the following information in mind while searching for O'ahu to Midway flight deals. Data was last updated January 7, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$360
(Southwest)

One-way from

$180
(Southwest)

Popular in

July

Cheapest in

February

Average price

$721
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
Search Deals
From O'ahu to Chicago Midway
Search Deals
One-way flight from O'ahu to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from O'ahu to Midway

Cheapest flights from O'ahu to Midway
Explore the most affordable flight options available from O'ahu to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 7, 2026.

This Southwest deal was found by Cheapflights users on 1/6. 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 3/181:50 pmHNL - MDW
1 stop11h 05mSouthwest
Tue 4/710:05 amMDW - HNL
1 stop15h 55mSouthwest
Deal found 1/6$360
This Delta deal was found by Cheapflights users on 1/7. 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 4/112:35 pmHNL - MDW
2 stops15h 18mDelta
Wed 4/89:30 amMDW - HNL
2 stops16h 22mDelta
Deal found 1/7$409
This Southwest deal was found by Cheapflights users on 1/7. 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.
Sun 3/159:25 pmHNL - MDW
1 stop15h 40mSouthwest
Tue 3/3110:30 amMDW - HNL
1 stop12h 10mSouthwest
Deal found 1/7$422
This Southwest deal was found by Cheapflights users on 1/6. 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.
Sun 2/18:05 amHNL - MDW
1 stop12h 20mSouthwest
Sat 2/78:25 amMDW - HNL
1 stop16h 35mSouthwest
Deal found 1/6$508
This Delta deal was found by Cheapflights users on 1/7. 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.
Fri 2/209:35 pmHNL - MDW
2 stops14h 39mDelta
Tue 3/36:00 amMDW - HNL
1 stop13h 11mDelta
Deal found 1/7$520

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'ahu 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 January 7, 2026.
Use the filters below to find and compare flights from O'ahu to Chicago Midway Airport that are best for you.

Fly from

O'ahu

Fly to

Midway

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/18

1:50 pm-5:55 am

1 stop11h 05m

Chicago Midway

Tue 4/7

10:05 am-9:00 pm

1 stop15h 55m

$360

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 3/15

9:25 pm-6:05 pm

1 stop15h 40m

Chicago Midway

Tue 3/31

10:30 am-5:40 pm

1 stop12h 10m

$422

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 2/1

9:30 pm-3:25 pm

2 stops13h 55m

Chicago Midway

Sat 2/7

8:25 am-9:00 pm

1 stop16h 35m

$514

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 2/20

9:35 pm-4:14 pm

2 stops14h 39m

Chicago Midway

Tue 3/3

6:00 am-3:11 pm

1 stop13h 11m

$520

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/1

3:48 pm-9:56 am

1 stop13h 08m

Chicago Midway

Wed 4/8

9:30 am-8:52 pm

2 stops16h 22m

$541

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 4/7

11:55 am-6:00 am

1 stop13h 05m

Chicago Midway

Sat 4/11

5:10 am-2:20 pm

2 stops14h 10m

$567

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 2/4

9:55 pm-12:30 pm

1 stop10h 35m

$180

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 2/4

2:44 pm-3:58 pm

2 stops45h 14m

$181

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/4

9:40 pm-11:51 pm

2 stops22h 11m

$181

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/4

4:50 pm-9:54 am

1 stop13h 04m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 15 results
1
2

Best time to book a flight from O'ahu to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from O'ahu 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 O'ahu to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated January 7, 2026.
Peruse reviews from past customers who have flown with Southwest from O'ahu to Chicago Midway Airport to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,249 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from O'ahu to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from O'ahu to Chicago Midway Airport?

    A quick flight from O'ahu to Chicago Midway Airport can take about 11h 05m. Southwest provides one of the quickest options available for as low as $360. O'ahu and Chicago Midway Airport are separated by a distance of 4243 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from O'ahu to Midway that include hotel bookings?

    Yes. In addition to deals on O'ahu to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'ahu to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'ahu to Midway.

  • Can I find deals for business class flights from O'ahu to Midway?

    Yes. Cheapflights offers flight deals from O'ahu to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top airline flying from O'ahu to Midway

Discover the top airline that operate flights from O'ahu 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 January 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$581Average$783FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.