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MDW - HNL

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

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$561
Typical prices: $642-$847
Southwest
Wed 2/7Mon 2/12
MDW - HNL • 2 stops
Cheapest one-way
$245
Typical prices: $284-$433
Southwest
Sat 11/3
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 41% compared to booking last minute.
Insights
Insights
When to travel
November
Cheapest • 29% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Oakland (OAK)
Cheapest • Avg $579 (round-trip)
Phoenix Sky Harbor Intl (PHX)
Shortest trip • 11h 22m (one-way)
Insights
Insights
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We hope you love your trip to Honolulu!
Flight Deals
Booking Insights
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

Sun, Feb 7 - Fri, Feb 12
Southwest Logo
10:15 am - 7:30 pmMDW  Chicago Midway-HNL Honolulu
13h 15m2 stops Denver Intl Los Angeles
Southwest Logo
3:15 pm - 5:50 amHNL  Honolulu-MDW Chicago Midway
10h 35m1 stop Oakland
$561Southwest
Thu, Nov 26 - Fri, Dec 11
Southwest Logo
6:05 am - 1:55 pmMDW  Chicago Midway-HNL Honolulu
11h 50m1 stop Las Vegas Harry Reid Intl
Southwest Logo
3:15 pm - 5:55 amHNL  Honolulu-MDW Chicago Midway
10h 40m1 stop Oakland
$562Southwest
Fri, Jan 29 - Fri, Feb 5
Southwest Logo
10:15 am - 7:45 pmMDW  Chicago Midway-HNL Honolulu
13h 30m1 stop Oakland
Southwest Logo
10:00 pm - 2:15 pmHNL  Honolulu-MDW Chicago Midway
12h 15m1 stop Los Angeles
$562Southwest
Sun, Jan 31 - Sat, Feb 6
Southwest Logo
6:55 am - 9:20 pmMDW  Chicago Midway-HNL Honolulu
18h 25m1 stop San Diego
Southwest Logo
3:15 pm - 11:45 amHNL  Honolulu-MDW Chicago Midway
16h 30m1 stop Oakland
$562Southwest
Sat, Jan 23 - Wed, Feb 3
Southwest Logo
10:05 am - 9:20 pmMDW  Chicago Midway-HNL Honolulu
15h 15m1 stop San Diego
Southwest Logo
9:00 pm - 2:55 pmHNL  Honolulu-MDW Chicago Midway
13h 55m1 stop Phoenix Sky Harbor Intl
$562Southwest
Tue, Jan 12 - Sat, Jan 16
Southwest Logo
10:05 am - 5:40 pmMDW  Chicago Midway-HNL Honolulu
11h 35m1 stop Las Vegas Harry Reid Intl
Southwest Logo
8:10 am - 10:15 pmHNL  Honolulu-MDW Chicago Midway
10h 05m1 stop San Diego
$562Southwest
Sun, Jan 31 - Sat, Feb 6
Southwest Logo
6:55 am - 9:20 pmMDW  Chicago Midway-HNL Honolulu
18h 25m1 stop San Diego
Southwest Logo
3:15 pm - 11:45 amHNL  Honolulu-MDW Chicago Midway
16h 30m1 stop Oakland
$562Southwest
Thu, Nov 5 - Thu, Nov 12
Southwest Logo
7:30 am - 9:10 pmMDW  Chicago Midway-HNL Honolulu
17h 40m2 stops Baltimore/Washington San Jose
Southwest Logo
10:50 pm - 5:55 pmHNL  Honolulu-MDW Chicago Midway
15h 05m1 stop San Jose
$564Southwest
Tue, Nov 3 - Tue, Nov 10
Delta Logo
6:04 am - 2:26 pmMDW  Chicago Midway-HNL Honolulu
12h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:35 pm - 8:50 amHNL  Honolulu-MDW Chicago Midway
15h 15m2 stops Los Angeles Minneapolis St Paul
$569Delta
Wed, Jan 13 - Wed, Jan 20
Delta Logo
9:30 am - 8:24 pmMDW  Chicago Midway-HNL Honolulu
14h 54m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
8:45 pm - 4:50 pmHNL  Honolulu-MDW Chicago Midway
16h 05m2 stops Salt Lake City Minneapolis St Paul
$574Delta
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 $642 to $847. The lowest price found in the past 5 days was $561, 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 15% cheaper than the average day, while Thursday is the most expensive, with prices 9% higher.

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

•November is the cheapest month to fly from Chicago Midway Airport to Honolulu at $537 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 64% 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 41% 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

October

Cheapest flight

$245
Beat the crowds with an average 59% drop in travelers.
The most popular month to fly with an average 55% 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 $642 to $847, with an average of $752 over the past 12 months. Anything below $642 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 3% above the $752 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 $248, which is 37% 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 $17 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) - 26% of one-stop connections
    • San Diego (SAN) - 26% of one-stop connections
    • Los Angeles (LAX) - 20% 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 23% on flights from Chicago Midway Airport to Honolulu. Wednesday is the cheapest departure day at $642 round-trip on average, while Thursday is the most expensive at $826, a difference of $184.

    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 22m, compared with 11h 48m via San Diego (SAN) and 12h 02m via Los Angeles (LAX).

  • 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 $642, about $184 less than Thursday fares (22% 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 41% 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 November. Fares historically average $537 round-trip in that month - typically $349 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