HNL - MDW

$223 Find Cheap Flights from Honolulu to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$470
Typical prices: $593-$783
Southwest
Mon 11/5Thu 11/8
HNL - MDW • 1 stop
Cheapest one-way
$223
Typical prices: $271-$392
Southwest
Sat 12/8
HNL - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Honolulu and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
October
Cheapest • 22% price drop
November
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Detroit Metropolitan Wayne County (DTW)
Cheapest • Avg $496 (round-trip)
Las Vegas Harry Reid Intl (LAS)
Shortest trip • 10h 57m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Honolulu to Midway (HNL-MDW)

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

Recent round-trip flight deals from Honolulu to Midway

Thu, Nov 5 - Sun, Nov 8
Southwest Logo
10:50 pm - 5:55 pmHNL  Honolulu-MDW Chicago Midway
15h 05m1 stop San Jose
Southwest Logo
7:25 am - 7:30 pmMDW  Chicago Midway-HNL Honolulu
16h 05m1 stop Los Angeles
$470Southwest
Tue, Oct 27 - Tue, Nov 3
Southwest Logo
1:10 pm - 5:55 amHNL  Honolulu-MDW Chicago Midway
11h 45m1 stop Oakland
Southwest Logo
10:00 am - 9:20 pmMDW  Chicago Midway-HNL Honolulu
15h 20m2 stops Las Vegas Harry Reid Intl San Diego
$476Southwest
Thu, Nov 5 - Sun, Nov 8
Southwest Logo
10:50 pm - 5:30 pmHNL  Honolulu-MDW Chicago Midway
14h 40m2 stops San Jose Los Angeles
Southwest Logo
7:25 am - 7:30 pmMDW  Chicago Midway-HNL Honolulu
16h 05m1 stop Los Angeles
$476Southwest
Mon, Oct 26 - Mon, Nov 2
Southwest Logo
8:55 pm - 3:45 pmHNL  Honolulu-MDW Chicago Midway
13h 50m1 stop Phoenix Sky Harbor Intl
Southwest Logo
10:10 am - 9:10 pmMDW  Chicago Midway-HNL Honolulu
15h 00m1 stop San Jose
$528Southwest
Tue, Oct 27 - Tue, Nov 3
Southwest Logo
1:10 pm - 5:55 amHNL  Honolulu-MDW Chicago Midway
11h 45m1 stop Oakland
Southwest Logo
10:05 am - 7:30 pmMDW  Chicago Midway-HNL Honolulu
13h 25m1 stop Los Angeles
$528Southwest
Tue, Nov 10 - Fri, Nov 13
Southwest Logo
3:15 pm - 5:55 amHNL  Honolulu-MDW Chicago Midway
10h 40m1 stop Oakland
Southwest Logo
10:05 am - 7:45 pmMDW  Chicago Midway-HNL Honolulu
13h 40m1 stop Oakland
$532Southwest
Mon, Oct 26 - Mon, Nov 2
Southwest Logo
9:55 pm - 3:45 pmHNL  Honolulu-MDW Chicago Midway
12h 50m2 stops San Diego Phoenix Sky Harbor Intl
Southwest Logo
7:25 am - 7:30 pmMDW  Chicago Midway-HNL Honolulu
16h 05m1 stop Los Angeles
$534Southwest
Tue, Nov 10 - Fri, Nov 13
Southwest Logo
3:15 pm - 5:55 amHNL  Honolulu-MDW Chicago Midway
10h 40m1 stop Oakland
Southwest Logo
7:25 am - 9:05 pmMDW  Chicago Midway-HNL Honolulu
17h 40m2 stops Los Angeles Sacramento Intl
$538Southwest
Thu, Nov 5 - Sat, Nov 14
Delta Logo
4:15 pm - 9:32 amHNL  Honolulu-MDW Chicago Midway
13h 17m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 8:57 pmMDW  Chicago Midway-HNL Honolulu
18h 57m2 stops Atlanta Hartsfield-Jackson Los Angeles
$584Delta
Tue, Oct 20 - Thu, Oct 22
Delta Logo
2:51 pm - 9:32 amHNL  Honolulu-MDW Chicago Midway
13h 41m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:04 am - 1:36 pmMDW  Chicago Midway-HNL Honolulu
12h 32m1 stop Atlanta Hartsfield-Jackson
$586Delta
Booking Insights

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

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

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

Round-trip flights from Honolulu to Chicago Midway Airport start at $470. Prices are below average for this route right now, with typical round-trip fares ranging from $593 to $783. The lowest price found in the past 5 days was $470 on Southwest.

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

Wednesday is the cheapest day of the week to fly from Honolulu to Chicago Midway Airport, it is 17% cheaper than the average day. Saturday is the most expensive day with flight prices 17% higher than average. Based on deals found by KAYAK users in the last 12 months.

Find deals

Key details for Honolulu to Chicago Midway Airport flights

Low season

April

Cheapest flight

$223
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Honolulu to Chicago Midway Airport

When to book flights from Honolulu to Midway

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

Your Honolulu to Chicago Midway Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

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

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

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

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

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

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

    • San Diego (SAN) - 36% of one-stop connections
    • Las Vegas Harry Reid Intl (LAS) - 27% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 18% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 9% of one-stop connections

    San Diego (SAN) handles the largest share of one-stop connections on this route.

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

    Yes. Being flexible with your travel dates can save you up to 29% on the Honolulu to Chicago Midway Airport route. Wednesday is the cheapest departure day at $593 round-trip on average, while Saturday is the most expensive at $830, a difference of $237. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

    A nonstop flight from Honolulu to Chicago Midway Airport takes 0h 00m, covering 4,243 miles.

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

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

    One-way fares from Honolulu to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $266, which is 28% below the typical average for this route.

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

    Flying via Las Vegas Harry Reid Intl (LAS) gives the shortest average 1-stop total travel time at 10h 57m, compared with 11h 09m via Phoenix Sky Harbor Intl (PHX) and 11h 18m via Detroit Metropolitan Wayne County (DTW).

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

    Chicago Midway Airport is 5 hours ahead of Honolulu (Central Time vs Hawaii-Aleutian Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

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

    Round-trip flights from Honolulu to Chicago Midway Airport range from $593 to $783, with an average of $708 over the past 12 months. Anything below $593 counts as a good deal.

Your guide to booking Honolulu to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Saturday. On this route, Wednesday flights average $593 - about $237 less than Saturday (29% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Honolulu to Chicago Midway Airport trip for October. Fares historically average $554 round-trip in that month - typically $314 less than the most expensive month, which is July (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

More options for your flight from Honolulu to Midway

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

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago