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Midway

$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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Hawaii to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Hawaii (USHI) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

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 November 21, 2024.

This Delta deal was found by Cheapflights users on 11/20. 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.
Mon 12/169:40 pmLIH - MDW
2 stops16h 52mDelta
Wed 1/89:34 amMDW - LIH
2 stops14h 35mDelta
Deal found 11/20$517
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/59:00 pmKOA - MDW
2 stops16h 01mDelta
Mon 12/99:30 amMDW - KOA
2 stops14h 19mDelta
Deal found 11/20$562
This Delta deal was found by Cheapflights users on 11/19. 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 11/225:00 pmHNL - MDW
1 stop12h 32mDelta
Tue 11/266:00 amMDW - HNL
1 stop13h 14mDelta
Deal found 11/19$571
This Southwest deal was found by Cheapflights users on 11/19. 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 11/2110:30 amHNL - MDW
2 stops18h 30mSouthwest
Mon 11/255:35 amMDW - HNL
1 stop15h 55mSouthwest
Deal found 11/19$619
This Southwest deal was found by Cheapflights users on 11/20. 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 12/168:15 amLIH - MDW
1 stop10h 10mSouthwest
Wed 1/88:35 pmMDW - LIH
2 stops23h 00mSouthwest
Deal found 11/20$662
This Delta deal was found by Cheapflights users on 11/19. 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.
Tue 12/101:21 pmOGG - MDW
2 stops15h 29mDelta
Sat 12/146:00 amMDW - OGG
1 stop15h 46mDelta
Deal found 11/19$853

Find flights from Hawaii to Midway within your budget

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 1/13

4:50 pm-8:54 am

1 stop12h 04m

Chicago Midway

Sun 1/19

6:00 am-2:56 pm

1 stop12h 56m

$503

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 12/16

9:40 pm-6:32 pm

2 stops16h 52m

Chicago Midway

Wed 1/8

9:34 am-8:09 pm

2 stops14h 35m

$517

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 12/5

9:00 pm-5:01 pm

2 stops16h 01m

Chicago Midway

Mon 12/9

9:30 am-7:49 pm

2 stops14h 19m

$562

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 4/8

8:30 pm-12:15 pm

1 stop10h 45m

Chicago Midway

Tue 4/15

5:35 am-1:00 pm

1 stop12h 25m

$584

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 4/1

8:10 am-11:35 pm

1 stop10h 25m

Chicago Midway

Mon 4/7

5:30 am-12:40 pm

1 stop12h 10m

$614

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 1/8

6:10 am-11:20 pm

2 stops13h 10m

Chicago Midway

Tue 1/21

7:20 am-3:50 pm

1 stop12h 30m

$635

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 12/16

8:15 am-10:25 pm

1 stop10h 10m

Chicago Midway

Wed 1/8

8:35 pm-3:35 pm

2 stops23h 00m

$662

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 12/10

1:21 pm-8:50 am

2 stops15h 29m

Chicago Midway

Sat 12/14

6:00 am-5:46 pm

1 stop15h 46m

$853

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/15

6:40 pm-1:08 pm

2 stops14h 28m

$216

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 12/23

4:45 pm-9:23 am

1 stop12h 38m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 16 results
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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.

Travel insights for flights from Hawaii to Midway

Get recent, data-driven insights about flights from Hawaii to Midway including ideal travel times, pricing trends, and more.

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 November 21, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Hawaii to Chicago Midway Airport as you normally would.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 November 21, 2024.
Get a feel of what it's like to fly with Delta and Southwest from Hawaii to Chicago by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,759 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,810 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • What are the cheapest airlines to fly from Hawaii to Chicago Midway Airport one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $216. However, be on the lookout for offers from Southwest and WestJet, as they are both options that can get you from Hawaii to Chicago Midway Airport for a low price.

  • 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.

  • What is the cheapest month to book a flight from Hawaii to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Hawaii to Chicago Midway Airport (average of $159). Flying from Hawaii to Chicago Midway Airport in July is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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.
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LaGuardia to Midway flights
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San Francisco to Midway flights
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Dulles Intl to Midway flights
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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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$421Average$926FlexibilityNo cancel feeOn-timeN/A
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