MDW - HNL

$245 Find Cheap Flights from Chicago Midway Airport to Honolulu - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$560
Typical prices: $645-$848
Southwest
Fri 10/19Sun 10/28
MDW - HNL • 1 stop
Cheapest one-way
$245
Typical prices: $322-$426
Southwest
Sat 10/27
MDW - HNL • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Honolulu. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
14 weeks
in advance
Our data shows that travelers who book at least 14 weeks in advance save around 44% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 15% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Oakland (OAK)
Cheapest • Avg $590 (round-trip)
Phoenix Sky Harbor Intl (PHX)
Shortest trip • 11h 08m (one-way)
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Insights
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We hope you love your trip to Honolulu!
Flight Deals
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Flight Deals

Cheap Flights from Midway to Honolulu (MDW-HNL)

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

Recent round-trip flight deals from Midway to Honolulu

Mon, Oct 19 - Wed, Oct 28
Southwest Logo
5:10 am - 11:50 amMDW  Chicago Midway-HNL Honolulu
11h 40m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:00 pm - 1:50 pmHNL  Honolulu-MDW Chicago Midway
11h 50m2 stops Las Vegas Harry Reid Intl Denver Intl
$560Southwest
Sat, Nov 7 - Wed, Nov 18
Delta Logo
4:19 pm - 12:04 pmMDW  Chicago Midway-HNL Honolulu
23h 45m2 stops Atlanta Hartsfield-Jackson Los Angeles
Delta Logo
1:35 pm - 8:50 amHNL  Honolulu-MDW Chicago Midway
15h 15m2 stops Los Angeles Minneapolis St Paul
$560Delta
Sat, Nov 7 - Wed, Nov 11
Delta Logo
4:19 pm - 12:04 pmMDW  Chicago Midway-HNL Honolulu
23h 45m2 stops Atlanta Hartsfield-Jackson Los Angeles
Delta Logo
1:35 pm - 9:46 amHNL  Honolulu-MDW Chicago Midway
16h 11m2 stops Los Angeles Detroit Metropolitan Wayne County
$560Delta
Sat, Nov 7 - Tue, Nov 10
Delta Logo
4:19 pm - 12:04 pmMDW  Chicago Midway-HNL Honolulu
23h 45m2 stops Atlanta Hartsfield-Jackson Los Angeles
Delta Logo
1:35 pm - 9:46 amHNL  Honolulu-MDW Chicago Midway
16h 11m2 stops Los Angeles Detroit Metropolitan Wayne County
$560Delta
Thu, Nov 5 - Tue, Nov 10
Southwest Logo
10:15 am - 9:05 pmMDW  Chicago Midway-HNL Honolulu
14h 50m1 stop Sacramento Intl
Southwest Logo
3:15 pm - 5:55 amHNL  Honolulu-MDW Chicago Midway
10h 40m1 stop Oakland
$562Southwest
Mon, Oct 26 - Mon, Nov 9
Southwest Logo
5:40 am - 1:15 pmMDW  Chicago Midway-HNL Honolulu
12h 35m1 stop Phoenix Sky Harbor Intl
Southwest Logo
8:15 am - 5:00 amHNL  Honolulu-MDW Chicago Midway
16h 45m1 stop San Jose
$562Southwest
Tue, Nov 3 - Mon, Nov 9
Southwest Logo
10:00 am - 7:45 pmMDW  Chicago Midway-HNL Honolulu
13h 45m1 stop Oakland
Southwest Logo
10:40 pm - 5:15 pmHNL  Honolulu-MDW Chicago Midway
14h 35m1 stop Sacramento Intl
$562Southwest
Thu, Nov 26 - Wed, Dec 2
Southwest Logo
6:05 am - 1:55 pmMDW  Chicago Midway-HNL Honolulu
11h 50m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:00 pm - 3:00 pmHNL  Honolulu-MDW Chicago Midway
14h 00m1 stop Phoenix Sky Harbor Intl
$562Southwest
Sun, Nov 1 - Thu, Nov 5
Southwest Logo
7:25 am - 9:05 pmMDW  Chicago Midway-HNL Honolulu
17h 40m2 stops Los Angeles Sacramento Intl
Southwest Logo
10:50 pm - 5:30 pmHNL  Honolulu-MDW Chicago Midway
14h 40m2 stops San Jose Los Angeles
$565Southwest
Tue, Nov 3 - Mon, Nov 9
Southwest Logo
10:00 am - 7:45 pmMDW  Chicago Midway-HNL Honolulu
13h 45m1 stop Oakland
Southwest Logo
10:15 pm - 5:20 pmHNL  Honolulu-MDW Chicago Midway
15h 05m2 stops Las Vegas Harry Reid Intl Omaha Eppley Airfield
$568Southwest
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Honolulu 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 Honolulu?

Round-trip flights from Chicago Midway Airport to Honolulu typically range from $645 to $848. The lowest price found in the past 5 days was $560, on Southwest.

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

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 Honolulu. It’s 13% cheaper than the average day, while Thursday is the most expensive, with prices 10% higher.

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

•February is the cheapest month to fly from Chicago Midway Airport to Honolulu at $637 round-trip.
•June ($886) and December ($848) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 39% 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 Honolulu the cheapest?

Flights from Chicago Midway Airport to Honolulu are cheapest 14 weeks before departure. Booking in this window typically costs about 44% 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 Honolulu flights

Low season

December

Cheapest flight

$245
Beat the crowds with an average 5% drop in travelers.
The most popular month to fly with an average 51% increase in travelers.
One-way flight from Chicago Midway Airport to Honolulu

When to book flights from Midway to Honolulu

Are your dates flexible? Find out the best times to travel from Midway to Honolulu 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 Honolulu 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 Honolulu?

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

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

    A nonstop flight from Chicago Midway Airport to Honolulu takes 00m, covering 4,243 miles.

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

    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 Honolulu flight?

    Round-trip flights from Chicago Midway Airport to Honolulu range from $645 to $848, with an average of $746 over the past 12 months. Anything below $645 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 5% above the $746 route average. Book 14 weeks before departure for the lowest fares.

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

    One-way fares from Chicago Midway Airport to Honolulu are currently lower than usual. Average one-way flight prices are about $266, which is 32% below the typical average for this route.

  • What car rental options are available at Honolulu Airport (HNL)?

    Honolulu Airport (HNL) hosts 5 major car rental companies, with daily rates starting from around $18 for economy cars. Top options include:

    • Thrifty
    • Dollar
    • Lucky Owl Car Rental
    • Hertz
    • Sixt

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

    Flights from Chicago Midway Airport to Honolulu usually depart from Chicago Midway (MDW) and arrive at Honolulu (HNL).

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

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

    • Las Vegas Harry Reid Intl (LAS) - 29% of one-stop connections
    • San Diego (SAN) - 25% of one-stop connections
    • Los Angeles (LAX) - 21% of one-stop connections
    • San Jose (SJC) - 13% of one-stop connections

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

    Yes. Flexible dates can save you up to 21% on flights from Chicago Midway Airport to Honolulu. Wednesday is the cheapest departure day at $653 round-trip on average, while Thursday is the most expensive at $826, a difference of $173.

    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 Honolulu?

    Flying via Phoenix Sky Harbor Intl (PHX) gives the shortest average 1-stop total travel time at 11h 08m, compared with 11h 43m via San Diego (SAN) and 12h 02m via Oakland (OAK).

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

    Honolulu 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 Honolulu?

    Some of the most popular sights in Honolulu are Waikiki Beach, Hawaii Convention Center and International Market Place. These are among the most viewed places in Honolulu on KAYAK.

Your guide to booking Chicago Midway Airport to Honolulu 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 Thursday. On this route, Wednesday flights average $653, about $173 less than Thursday fares (21% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 14 weeks before you fly. On this route, that window historically saves about 44% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Honolulu trip for February. Fares historically average $637 round-trip in that month - typically $249 less than the most expensive month, which is June (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Honolulu Airport.

    • Airport Honolulu Hotel, Trademark Collection by Wyndham
    • Pacific Marina Inn Airport Hotel
    • Best Western The Plaza Hotel Honolulu Airport

More options for your flight from Midway to Honolulu

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

Car rentals in Honolulu
Hotels in Honolulu
Vacations in Honolulu