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$202+ Cheap flights from Midway (MDW) to Hawaii

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Midway to Hawaii

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Hawaii (USHI). 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 Midway to Hawaii

Cheapest flights from Midway to Hawaii
Explore the most affordable flight options available from Midway to Hawaii. 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 12/96:00 amMDW - OGG
1 stop15h 46mDelta
Fri 12/1311:45 pmOGG - MDW
2 stops14h 47mDelta
Deal found 11/20$477
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.
Wed 12/119:30 amMDW - LIH
2 stops14h 45mDelta
Tue 12/179:40 pmLIH - MDW
2 stops16h 52mDelta
Deal found 11/20$537
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.
Sat 12/79:30 amMDW - KOA
2 stops14h 19mDelta
Sat 12/149:30 pmKOA - MDW
2 stops17h 02mDelta
Deal found 11/20$537
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 11/289:31 amMDW - HNL
2 stops13h 59mDelta
Sat 12/76:39 pmHNL - MDW
2 stops14h 11mDelta
Deal found 11/20$581
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.
Fri 12/136:40 amMDW - KOA
1 stop13h 00mSouthwest
Fri 12/207:30 amKOA - MDW
1 stop12h 20mSouthwest
Deal found 11/19$588
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.
Sat 12/78:10 pmMDW - LIH
2 stops21h 35mSouthwest
Sat 12/148:15 amLIH - MDW
2 stops21h 00mSouthwest
Deal found 11/20$601
This Kissandfly.com 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3010:04 pmMDW - HNL
2 stops23h 37mFrontier
Mon 1/134:50 pmHNL - MDW
1 stop12h 04mFrontier
Deal found 11/19$609
This Southwest deal was found by Cheapflights users on 11/21. 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 12/119:45 amMDW - HNL
1 stop11h 45mSouthwest
Tue 12/1710:30 amHNL - MDW
2 stops20h 00mSouthwest
Deal found 11/21$612
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 12/165:35 amMDW - OGG
1 stop12h 00mSouthwest
Thu 12/197:45 amOGG - MDW
2 stops13h 05mSouthwest
Deal found 11/20$662
This Kissandfly.com 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/308:41 pmMDW - HNL
2 stops21h 34mMultiple Airlines
Mon 1/1310:55 pmHNL - MDW
3 stops-6h 0-41mMultiple Airlines
Deal found 11/20$674
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.
Tue 12/248:40 pmMDW - ITO
2 stops25h 35mSouthwest
Sat 12/286:00 amITO - MDW
2 stops15h 15mSouthwest
Deal found 11/20$762
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 12/56:00 amMDW - ITO
2 stops17h 25mDelta
Mon 12/912:50 pmITO - MDW
2 stops16h 08mDelta
Deal found 11/20$1,256

Find flights from Midway to Hawaii within your budget

Customize your flight search to find flights from Midway to Hawaii 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

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 1/12

10:19 am-10:01 pm

2 stops15h 42m

Honolulu

Wed 1/22

4:50 pm-8:54 am

1 stop12h 04m

$427

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 1/13

6:00 am-5:39 pm

1 stop15h 39m

Kahului

Fri 1/17

9:19 pm-4:12 pm

2 stops14h 53m

$448

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/16

7:00 am-6:45 pm

2 stops15h 45m

Honolulu

Thu 1/23

8:20 am-10:40 pm

1 stop10h 20m

$469

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Thu 1/16

5:30 am-7:50 pm

2 stops18h 20m

Lihue

Thu 1/23

9:00 am-11:20 pm

1 stop10h 20m

$482

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 3/4

7:20 am-4:20 pm

1 stop13h 00m

Kahului

Tue 3/11

11:20 am-5:20 am

1 stop13h 00m

$504

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/4

9:34 am-8:09 pm

2 stops14h 35m

Lihue

Fri 2/14

9:34 pm-4:12 pm

2 stops14h 38m

$517

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sat 12/7

9:30 am-7:49 pm

2 stops14h 19m

Kona Intl

Sat 12/14

9:30 pm-6:32 pm

2 stops17h 02m

$537

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 1/2

10:45 pm-12:50 pm

2 stops18h 05m

Kona Intl

Fri 1/17

9:00 am-12:05 am

1 stop11h 05m

$565

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 12/30

8:41 pm-2:15 pm

2 stops21h 34m

Honolulu

Mon 1/13

10:55 pm-8:14 pm

3 stops-6h 0-41m

$674

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 1/26

9:25 pm-6:15 pm

2 stops24h 50m

Hilo Intl

Sat 2/1

6:00 am-10:40 pm

2 stops12h 40m

$702

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 22 results
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Best time to book a flight from Midway to Hawaii

Have a flexible travel schedule? Discover the best time to fly to Hawaii from Midway 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 Midway to Hawaii

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $469). Flying from Chicago Midway Airport to Hawaii in June is currently the most expensive (average of $687). 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.

What is the cheapest time of day to fly from MDW to HI?

Find hourly flight availability from Midway to Hawaii. 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 Chicago Midway Airport to Hawaii as you normally would.

Rainfall in Hawaii by month

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

In terms of precipitation, rainfall in Hawaii ranges from 0.3 - 3.2 inches per month. December is typically the wettest month, when rainfall can reach 3.2 in. June is typically the driest time to visit Hawaii when rainfall is around 0.3 in.

Temperature in Hawaii by month

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

If weather is an important factor for your trip to Hawaii, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

Reviews of airlines servicing Hawaii

Get insights into the airlines that provide service to Hawaii. 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 Hawaii. Reviews last updated November 21, 2024.
Read through reviews of airlines operating flights from Chicago to Hawaii, such as Delta and Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

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

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

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

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

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 Midway to Hawaii. 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 Chicago Midway Airport to Hawaii one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $202. However, be on the lookout for offers from Southwest and WestJet, as they are both options that can get you from Chicago Midway Airport to Hawaii for a low price.

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

    While some choose either Chicago Midway - Kahului or Chicago Midway - Kona Intl, Chicago Midway - Honolulu is the most popular route from Chicago Midway Airport to Hawaii.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Hawaii 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 Chicago Midway Airport to Hawaii?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $469). Flying from Chicago Midway Airport to Hawaii in June is currently the most expensive (average of $687). 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.

See more FAQs

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Alternative routes for Midway to Hawaii

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Midway to Hawaii

Discover the top 2 airlines that operate flights from Midway to Hawaii. 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$453Average$902FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$479Average$696FlexibilityNo cancel feeOn-time63%
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