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MDW - OGG

$241 Find Cheap Flights from Chicago Midway Airport to Kahului - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$570
Typical prices: $690-$884
Southwest
Sat 10/20Sat 10/27
MDW - OGG • 1 stop
Cheapest one-way
$241
Typical prices: $356-$488
Southwest
Sat 11/10
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
13 weeks
in advance
Our data shows that travelers who book at least 13 weeks in advance save around 51% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 41% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
San Diego (SAN)
Cheapest • Avg $785 (round-trip)
Phoenix Sky Harbor Intl (PHX)
Shortest trip • 10h 27m (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, Dec 3 - Tue, Dec 8
Southwest Logo
5:50 am - 1:10 pmMDW  Chicago Midway-OGG Kahului
11h 20m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:25 pm - 3:00 pmOGG  Kahului-MDW Chicago Midway
13h 35m2 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl
$568Southwest
Tue, Oct 20 - Tue, Oct 27
Southwest Logo
6:05 am - 12:40 pmMDW  Chicago Midway-OGG Kahului
11h 35m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:55 pm - 5:05 pmOGG  Kahului-MDW Chicago Midway
14h 10m1 stop San Diego
$570Southwest
Thu, Dec 3 - Tue, Dec 8
Southwest Logo
5:50 am - 2:40 pmMDW  Chicago Midway-OGG Kahului
12h 50m2 stops Las Vegas Harry Reid Intl San Diego
Southwest Logo
9:25 pm - 3:00 pmOGG  Kahului-MDW Chicago Midway
13h 35m2 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl
$573Southwest
Tue, Jan 19 - Tue, Jan 26
Southwest Logo
5:20 am - 4:40 pmMDW  Chicago Midway-OGG Kahului
15h 20m2 stops Phoenix Sky Harbor Intl Honolulu
Southwest Logo
10:30 pm - 12:40 pmOGG  Kahului-MDW Chicago Midway
10h 10m1 stop Oakland
$576Southwest
Wed, Feb 24 - Tue, Mar 2
Southwest Logo
5:20 am - 2:50 pmMDW  Chicago Midway-OGG Kahului
13h 30m2 stops Phoenix Sky Harbor Intl San Diego
Southwest Logo
8:15 pm - 11:20 amOGG  Kahului-MDW Chicago Midway
11h 05m1 stop Phoenix Sky Harbor Intl
$576Southwest
Tue, Nov 17 - Tue, Nov 24
Southwest Logo
5:50 am - 2:50 pmMDW  Chicago Midway-OGG Kahului
13h 00m2 stops Las Vegas Harry Reid Intl Lihue
Southwest Logo
9:25 pm - 1:10 pmOGG  Kahului-MDW Chicago Midway
11h 45m1 stop Las Vegas Harry Reid Intl
$577Southwest
Tue, Nov 17 - Tue, Dec 1
Southwest Logo
5:50 am - 2:50 pmMDW  Chicago Midway-OGG Kahului
13h 00m2 stops Las Vegas Harry Reid Intl Lihue
Southwest Logo
11:20 pm - 5:25 pmOGG  Kahului-MDW Chicago Midway
14h 05m1 stop San Diego
$577Southwest
Thu, Dec 3 - Tue, Dec 8
Southwest Logo
5:50 am - 1:10 pmMDW  Chicago Midway-OGG Kahului
11h 20m1 stop Las Vegas Harry Reid Intl
Southwest Logo
10:30 pm - 12:30 pmOGG  Kahului-MDW Chicago Midway
10h 00m1 stop Oakland
$578Southwest
Mon, Nov 16 - Wed, Nov 25
Delta Logo
6:00 am - 2:29 pmMDW  Chicago Midway-OGG Kahului
12h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:59 pm - 10:25 amOGG  Kahului-MDW Chicago Midway
12h 26m1 stop Minneapolis St Paul
$586Delta
Mon, Nov 16 - Tue, Nov 24
Delta Logo
6:00 am - 2:29 pmMDW  Chicago Midway-OGG Kahului
12h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:59 pm - 8:50 amOGG  Kahului-MDW Chicago Midway
10h 51m1 stop Minneapolis St Paul
$586Delta
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 $690 to $884. The lowest price found in the past 5 days was $570, 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, Thursday is the cheapest day of the week to fly from Chicago Midway Airport to Kahului. It’s 15% cheaper than the average day, while Saturday is the most expensive, with prices 14% 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 $480 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 123% 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 13 weeks before departure. Booking in this window typically costs about 51% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Chicago Midway Airport to Kahului flights

Low season

January

Cheapest flight

$241
Beat the crowds with an average 68% drop 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 $690 to $884, with an average of $816 over the past 12 months. Anything below $690 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 5% above the $816 route average. Book 13 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 $363, which is 17% 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 starting from around $23 for economy cars. Top options include:

    • Dollar
    • Thrifty
    • Ace
    • Fox
    • Hertz

  • 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) - 38% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 35% of one-stop connections
    • San Diego (SAN) - 26% 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 25% on flights from Chicago Midway Airport to Kahului. Thursday is the cheapest departure day at $701 round-trip on average, while Saturday is the most expensive at $934, a difference of $233.

    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 27m, compared with 11h via Las Vegas Harry Reid Intl (LAS) and 11h 14m via San Diego (SAN).

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

    Kahului is 5 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 Thursday departure and avoid flying on Saturday. On this route, Thursday flights average $701, about $233 less than Saturday fares (25% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 13 weeks before you fly. On this route, that window historically saves about 51% 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 $480 round-trip in that month - typically $594 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