MDW - OGG

$291 Find Cheap Flights from Chicago Midway Airport to Kahului - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$586
Typical prices: $698-$893
Southwest
Sun 1/21Thu 1/25
MDW - OGG • 1 stop
Cheapest one-way
$291
Typical prices: $371-$488
Southwest
Sat 12/15
MDW - OGG • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Kahului. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
8 weeks
in advance
Our data shows that travelers who book at least 8 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 38% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Phoenix Sky Harbor Intl (PHX)
Cheapest • Avg $821 (round-trip)
Las Vegas Harry Reid Intl (LAS)
Shortest trip • 11h (one-way)
Insights
Insights
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We hope you love your trip to Kahului!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Kahului (MDW-OGG)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Kahului

Thu, Jan 21 - Mon, Jan 25
Southwest Logo
5:20 am - 1:10 pmMDW  Chicago Midway-OGG Kahului
11h 50m1 stop Phoenix Sky Harbor Intl
Southwest Logo
9:45 pm - 3:00 pmOGG  Kahului-MDW Chicago Midway
13h 15m1 stop Phoenix Sky Harbor Intl
$586Southwest
Thu, Jan 21 - Mon, Jan 25
Southwest Logo
10:15 am - 8:25 pmMDW  Chicago Midway-OGG Kahului
14h 10m2 stops Los Angeles Honolulu
Southwest Logo
9:45 pm - 12:25 pmOGG  Kahului-MDW Chicago Midway
10h 40m1 stop Phoenix Sky Harbor Intl
$592Southwest
Thu, Jan 21 - Mon, Jan 25
Southwest Logo
10:15 am - 8:25 pmMDW  Chicago Midway-OGG Kahului
14h 10m2 stops Los Angeles Honolulu
Southwest Logo
11:10 pm - 4:35 pmOGG  Kahului-MDW Chicago Midway
13h 25m2 stops San Diego Denver Intl
$597Southwest
Mon, Jan 11 - Tue, Jan 19
Southwest Logo
5:20 am - 1:10 pmMDW  Chicago Midway-OGG Kahului
11h 50m1 stop Phoenix Sky Harbor Intl
Southwest Logo
9:45 pm - 12:25 pmOGG  Kahului-MDW Chicago Midway
10h 40m1 stop Phoenix Sky Harbor Intl
$601Southwest
Thu, Mar 4 - Thu, Mar 11
Delta Logo
9:46 am - 4:47 pmMDW  Chicago Midway-OGG Kahului
11h 01m1 stop Minneapolis St Paul
Delta Logo
1:15 pm - 8:49 amOGG  Kahului-MDW Chicago Midway
15h 34m2 stops Los Angeles Minneapolis St Paul
$602Delta
Thu, Jan 7 - Mon, Jan 11
Delta Logo
9:38 am - 8:17 pmMDW  Chicago Midway-OGG Kahului
14h 39m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
5:57 pm - 8:58 amOGG  Kahului-MDW Chicago Midway
11h 01m1 stop Minneapolis St Paul
$602Delta
Mon, Mar 1 - Mon, Mar 8
Southwest Logo
10:10 am - 8:25 pmMDW  Chicago Midway-OGG Kahului
14h 15m2 stops San Diego Honolulu
Southwest Logo
11:10 pm - 4:35 pmOGG  Kahului-MDW Chicago Midway
13h 25m2 stops San Diego Denver Intl
$607Southwest
Thu, Jan 7 - Mon, Jan 11
Delta Logo
9:38 am - 8:17 pmMDW  Chicago Midway-OGG Kahului
14h 39m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
1:15 pm - 9:16 amOGG  Kahului-MDW Chicago Midway
16h 01m2 stops Los Angeles Detroit Metropolitan Wayne County
$607Delta
Sun, Jan 10 - Fri, Jan 15
Delta Logo
9:38 am - 8:17 pmMDW  Chicago Midway-OGG Kahului
14h 39m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
5:57 pm - 1:17 pmOGG  Kahului-MDW Chicago Midway
15h 20m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
$608Delta
Mon, Nov 30 - Mon, Dec 7
Southwest Logo
10:55 pm - 12:55 pmMDW  Chicago Midway-OGG Kahului
18h 00m1 stop Phoenix Sky Harbor Intl
Southwest Logo
9:25 pm - 2:15 pmOGG  Kahului-MDW Chicago Midway
12h 50m1 stop Las Vegas Harry Reid Intl
$609Southwest
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Kahului flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Kahului?

Round-trip flights from Chicago Midway Airport to Kahului typically range from $698 to $893. The lowest price found in the past 5 days was $586, on Southwest.

What's the cheapest day of the week to fly from Chicago Midway Airport to Kahului?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago Midway Airport to Kahului. It’s 17% cheaper than the average day, while Saturday is the most expensive, with prices 22% higher.

What’s the cheapest month to fly from Chicago Midway Airport to Kahului?

•January is the cheapest month to fly from Chicago Midway Airport to Kahului at $515 round-trip.
•March ($1,074) and June ($887) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 108% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to Kahului the cheapest?

Flights from Chicago Midway Airport to Kahului are cheapest 8 weeks before departure. Booking in this window typically costs about 26% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Chicago Midway Airport to Kahului flights

Low season

January

Cheapest flight

$291
Beat the crowds with an average 66% drop in travelers.
The most popular month to fly with an average 127% increase in travelers.
One-way flight from Chicago Midway Airport to Kahului

When to book flights from Midway to Kahului

Are your dates flexible? Find out the best times to travel from Midway to Kahului based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Kahului flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago Midway Airport to Kahului?

    Only Economy Class is available on flights from Chicago Midway Airport to Kahului.

  • How long is a flight from Chicago Midway Airport to Kahului?

    A nonstop flight from Chicago Midway Airport to Kahului takes 00m, covering 4,184 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Kahului?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to Kahului flight?

    Round-trip flights from Chicago Midway Airport to Kahului range from $698 to $893, with an average of $827 over the past 12 months. Anything below $698 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to Kahului flights?

    Last-minute fares on this route (booked within two weeks of departure) run 6% above the $827 route average. Book 8 weeks before departure for the lowest fares.

  • How are flight prices from Chicago Midway Airport to Kahului looking right now?

    One-way fares from Chicago Midway Airport to Kahului are currently lower than usual. Average one-way flight prices are about $300, which is 33% below the typical average for this route.

  • What car rental options are available at Kahului Airport (OGG)?

    Kahului Airport (OGG) hosts 5 major car rental companies, with daily rates averaging $64 for economy cars. Top options include:

    • Dollar
    • Thrifty
    • Hertz
    • Fox
    • Sixt

  • Which airports can I use when flying from Chicago Midway Airport to Kahului?

    Flights from Chicago Midway Airport to Kahului usually depart from Chicago Midway (MDW) and arrive at Kahului (OGG).

  • Which airports do connecting flights from Chicago Midway Airport to Kahului pass through?

    One-stop flights from Chicago Midway Airport to Kahului most commonly connect through:

    • Las Vegas Harry Reid Intl (LAS) - 49% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 33% of one-stop connections
    • San Diego (SAN) - 18% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Kahului?

    Yes. Flexible dates can save you up to 32% on flights from Chicago Midway Airport to Kahului. Wednesday is the cheapest departure day at $688 round-trip on average, while Saturday is the most expensive at $1,009, a difference of $321.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Kahului?

    Flying via Phoenix Sky Harbor Intl (PHX) gives the shortest average 1-stop total travel time at 10h 29m, compared with 11h via Las Vegas Harry Reid Intl (LAS) and 11h 19m via San Diego (SAN).

  • What is the time difference between Chicago Midway Airport and Kahului?

    Kahului is 4 hours behind Chicago Midway Airport (Hawaii-Aleutian Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Kahului?

    Maui Swap Meet is one of the most viewed places in Kahului on KAYAK.

Your guide to booking Chicago Midway Airport to Kahului flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Saturday. On this route, Wednesday flights average $688, about $321 less than Saturday fares (32% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 8 weeks before you fly. On this route, that window historically saves about 26% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Kahului trip for January. Fares historically average $515 round-trip in that month - typically $559 less than the most expensive month, which is March (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Kahului Airport.

    • Courtyard by Marriott Maui Kahului Airport

More options for your flight from Midway to Kahului

Complete your trip to Kahului with a hotel stay or car rental

Car rentals in Kahului
Hotels in Kahului
Vacations in Kahului