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Midway

$283+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Mar 1 — Mar 81
Sat 3/1
Sat 3/8
1 adult, Economy
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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 February 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$560
(Trip.com)

One-way from

$283
(Delta)

Popular in

June

Cheapest in

October

Average price

$736
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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From O'ahu to Chicago Midway
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One-way flight from O'ahu to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($112 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 24, 2025.

This Delta deal was found by Cheapflights users on 2/22. 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 3/411:25 pmHNL - MDW
2 stops14h 18mDelta
Mon 3/106:00 amMDW - HNL
1 stop13h 19mDelta
Deal found 2/22$515
This Trip.com deal was found by Cheapflights users on 2/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/97:40 amHNL - MDW
2 stops20h 44mMultiple Airlines
Wed 4/166:45 amMDW - HNL
2 stops43h 05mMultiple Airlines
Deal found 2/23$560
This Southwest deal was found by Cheapflights users on 2/23. 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 9/298:05 amHNL - MDW
1 stop11h 25mSouthwest
Mon 10/69:35 pmMDW - HNL
1 stop17h 45mSouthwest
Deal found 2/23$633

Find flights from O'ahu to Midway within your budget

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 February 24, 2025.

Fly from

O'ahu

Fly to

Midway

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/9

7:40 am-9:24 am

2 stops20h 44m

Chicago Midway

Wed 4/16

6:45 am-8:50 pm

2 stops43h 05m

$560

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/2

3:50 pm-8:43 am

1 stop11h 53m

Chicago Midway

Wed 4/9

10:25 am-8:53 pm

2 stops15h 28m

$624

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 4/14

11:15 am-9:20 am

2 stops17h 05m

Chicago Midway

Mon 4/28

9:25 pm-10:05 am

1 stop17h 40m

$683

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/5

5:05 pm-10:12 am

1 stop13h 07m

$283

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 3/4

8:20 am-10:40 pm

1 stop10h 20m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

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.

Travel insights for flights from O'ahu to Midway

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

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

Find hourly flight availability from O'ahu 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 February 24, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from O'ahu 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 February 24, 2025.
Southwest
8.1
Very good
4,380 reviews

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest
8.1
Very good
4,380 reviews
Southwest
8.1
Very good
4,380 reviews

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta
8.0
Very good
8,175 reviews
Southwest
8.1
Very good
4,380 reviews

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

  • 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.

  • What is the cheapest month to book a flight from O'ahu to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from O'ahu to Chicago Midway Airport (average of $160). Flying from O'ahu to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near O'ahu?

Book flights to O'ahu if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 2 airlines flying from O'ahu to Midway

Discover the top 2 airlines 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 February 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$418Average$617FlexibilityNo cancel feeOn-time63%
DeltaCheapest$421Average$926FlexibilityNo cancel feeOn-timeN/A
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