HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$181+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
feb. 14 — feb. 211
sáb. 2/14
sáb. 2/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hawaii 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 Hawaii to Midway

Keep the following information in mind while searching for Hawaii to Midway flight deals. Data was last updated enero 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$430
(Delta)

One-way from

$181
(Southwest)

Popular in

July

Cheapest in

February

Average price

$720
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 Hawaii to Chicago Midway
Search Deals
One-way flight from Hawaii to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($112 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from Hawaii to Midway

Cheapest flights from Hawaii to Midway
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 enero 15, 2026.

This Southwest deal was found by Cheapflights users on 1/13. 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.
jue. 1/299:55 pm
HNL
-
MDW
1 stop10h 40m
Southwest
mié. 2/48:25 am
MDW
-
HNL
1 stop12h 05m
Southwest
Deal found 1/13$362
This Delta deal was found by Cheapflights users on 1/14. 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.
vie. 2/134:45 pm
HNL
-
MDW
1 stop12h 09m
Delta
lun. 2/239:34 am
MDW
-
HNL
2 stops15h 54m
Delta
Deal found 1/14$430
This Southwest deal was found by Cheapflights users on 1/15. 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.
vie. 2/139:55 pm
HNL
-
MDW
1 stop11h 30m
Southwest
dom. 2/2210:50 am
MDW
-
HNL
1 stop14h 10m
Southwest
Deal found 1/15$432
This Delta deal was found by Cheapflights users on 1/14. 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.
mié. 2/1810:55 pm
KOA
-
MDW
2 stops14h 42m
Delta
dom. 2/229:34 am
MDW
-
KOA
2 stops14h 05m
Delta
Deal found 1/14$435
This Delta deal was found by Cheapflights users on 1/15. 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.
vie. 2/131:55 pm
HNL
-
MDW
2 stops17h 08m
Delta
dom. 2/229:34 am
MDW
-
HNL
2 stops16h 20m
Delta
Deal found 1/15$435
This Delta deal was found by Cheapflights users on 1/13. 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.
mié. 4/13:30 pm
HNL
-
MDW
1 stop12h 23m
Delta
mié. 4/89:30 am
MDW
-
HNL
2 stops16h 23m
Delta
Deal found 1/13$450
This Delta deal was found by Cheapflights users on 1/13. 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.
mié. 2/1110:55 pm
HNL
-
MDW
2 stops15h 45m
Delta
mié. 2/259:50 am
MDW
-
HNL
2 stops16h 04m
Delta
Deal found 1/13$453
This Delta deal was found by Cheapflights users on 1/12. 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.
vie. 2/271:55 pm
HNL
-
MDW
2 stops17h 08m
Delta
vie. 3/69:34 am
MDW
-
HNL
2 stops15h 54m
Delta
Deal found 1/12$455
This Delta deal was found by Cheapflights users on 1/12. 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.
mar. 2/171:55 pm
HNL
-
MDW
2 stops14h 59m
Delta
lun. 3/26:00 am
MDW
-
HNL
1 stop13h 11m
Delta
Deal found 1/12$480
This Southwest deal was found by Cheapflights users on 1/13. 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.
jue. 2/268:05 am
HNL
-
MDW
2 stops12h 45m
Southwest
dom. 3/110:15 pm
MDW
-
HNL
1 stop17h 00m
Southwest
Deal found 1/13$484
This Delta deal was found by Cheapflights users on 1/13. 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.
vie. 2/69:20 pm
LIH
-
MDW
2 stops14h 56m
Delta
lun. 2/99:33 am
MDW
-
LIH
2 stops14h 21m
Delta
Deal found 1/13$485
This Delta deal was found by Cheapflights users on 1/12. 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.
mar. 2/171:55 pm
HNL
-
MDW
2 stops14h 59m
Delta
mar. 3/39:34 am
MDW
-
HNL
2 stops15h 54m
Delta
Deal found 1/12$485

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 enero 15, 2026.
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

jue. 1/29

9:55 pm-12:35 pm

1 stop10h 40m

Chicago Midway

mié. 2/4

8:25 am-4:30 pm

1 stop12h 05m

$362

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

vie. 2/13

4:45 pm-8:54 am

1 stop12h 09m

Chicago Midway

lun. 2/23

9:34 am-9:28 pm

2 stops15h 54m

$430

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

jue. 2/26

8:05 am-12:35 am

1 stop12h 30m

Chicago Midway

dom. 3/1

10:15 pm-11:15 am

1 stop17h 00m

$432

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

vie. 2/13

9:55 pm-1:25 pm

1 stop11h 30m

Chicago Midway

dom. 2/22

10:50 am-9:00 pm

1 stop14h 10m

$432

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

mié. 2/18

10:55 pm-5:37 pm

2 stops14h 42m

Chicago Midway

dom. 2/22

9:34 am-7:39 pm

2 stops14h 05m

$435

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

vie. 2/13

1:55 pm-11:03 am

2 stops17h 08m

Chicago Midway

dom. 2/22

9:34 am-9:54 pm

2 stops16h 20m

$435

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

mié. 4/1

3:30 pm-8:53 am

1 stop12h 23m

Chicago Midway

mié. 4/8

9:30 am-8:53 pm

2 stops16h 23m

$450

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

vie. 2/27

1:55 pm-11:03 am

2 stops17h 08m

Chicago Midway

vie. 3/6

9:34 am-9:28 pm

2 stops15h 54m

$455

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

mar. 2/17

1:55 pm-8:54 am

2 stops14h 59m

Chicago Midway

mar. 3/3

6:00 am-3:11 pm

1 stop13h 11m

$480

LihueChicago

LIH - MDW

LIHMDW

Lihue

vie. 2/6

9:20 pm-4:16 pm

2 stops14h 56m

Chicago Midway

lun. 2/9

9:33 am-7:54 pm

2 stops14h 21m

$485

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 53 results
1
2
3
...
6

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
No data available for this route at this time. Please check back soon.

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.

  • How long is the flight from Hawaii to Chicago Midway Airport?

    Departing from Hawaii to Chicago Midway Airport will take you 10h 40m. The distance between Hawaii and Chicago Midway Airport is about 4243 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Hawaii to Chicago Midway Airport?

    Most travelers choose Honolulu - Chicago Midway, Kona Intl - Chicago Midway or Lihue - Chicago Midway when deciding on the best route from Hawaii to Chicago Midway Airport.

  • Can I find deals for flights from Hawaii to Midway that include hotel bookings?

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

  • How can I find direct flights from Hawaii to Midway?

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

  • Can I find deals for business class flights from Hawaii to Midway?

    Yes. Cheapflights offers flight deals from Hawaii 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.

Alternative routes for Hawaii to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Dulles Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Boston to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Denver to O'Hare Intl flights
Newark to Midway flights
Atlanta to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Seattle to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Los Angeles to Midway flights
Santa Ana to O'Hare Intl flights
Austin to O'Hare Intl flights
Ontario to O'Hare Intl flights
Dulles Intl to Midway flights
Atlanta to Midway flights
Charlotte to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Hobby to Midway flights
Love Field to O'Hare Intl flights
Baltimore to Midway flights
Minneapolis to Midway flights
San Francisco to Midway flights
San Diego to O'Hare Intl flights
Orlando to O'Hare Intl flights
Denver to Midway flights
LaGuardia to Midway flights
Orlando to Midway flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Love Field to Midway flights
Miami to O'Hare Intl flights
Boston to Midway flights
Tampa to Midway flights
Hartford to O'Hare Intl flights
Nashville to O'Hare Intl flights
Portland to O'Hare Intl flights

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 enero 15, 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.