$221 Find Cheap Flights from Chicago Midway Airport to Maui

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Maui departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maui

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Book Cheap Midway to Maui Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Maui that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Maui

Thu, Apr 16 - Thu, Apr 16
Southwest Logo
5:25 am - 2:50 pm
MDW
-
OGG
14h 25m
2 stops
Southwest Logo
8:55 pm - 5:55 pm
OGG
-
MDW
16h 00m
1 stop
$478Southwest
Mon, Apr 6 - Tue, Apr 14
Delta Logo
6:00 am - 3:13 pm
MDW
-
OGG
14h 13m
1 stop
Delta Logo
10:30 pm - 6:36 pm
OGG
-
MDW
15h 06m
2 stops
$479Delta
Mon, Apr 27 - Sun, May 3
Southwest Logo
6:40 am - 12:35 pm
MDW
-
OGG
10h 55m
1 stop
Southwest Logo
7:00 pm - 12:45 pm
OGG
-
MDW
12h 45m
2 stops
$481Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
6:00 am - 2:10 pm
MDW
-
OGG
13h 10m
2 stops
Southwest Logo
8:55 pm - 2:30 pm
OGG
-
MDW
12h 35m
1 stop
$482Southwest
Wed, Apr 29 - Wed, Apr 29
Southwest Logo
6:10 am - 2:45 pm
MDW
-
OGG
13h 35m
2 stops
Southwest Logo
8:25 pm - 11:55 am
OGG
-
MDW
10h 30m
1 stop
$485Southwest
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
7:55 am - 4:35 pm
MDW
-
OGG
13h 40m
2 stops
Southwest Logo
8:55 pm - 5:55 pm
OGG
-
MDW
16h 00m
1 stop
$507Southwest
Mon, Apr 27 - Sun, May 3
Southwest Logo
6:40 am - 12:35 pm
MDW
-
OGG
10h 55m
1 stop
Southwest Logo
12:40 pm - 5:00 am
OGG
-
MDW
11h 20m
1 stop
$512Southwest
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
6:10 am - 2:45 pm
MDW
-
OGG
13h 35m
2 stops
Southwest Logo
8:25 pm - 2:20 pm
OGG
-
MDW
12h 55m
2 stops
$513Southwest
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
6:45 am - 12:35 pm
MDW
-
OGG
10h 50m
1 stop
Southwest Logo
8:55 pm - 5:55 pm
OGG
-
MDW
16h 00m
1 stop
$523Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
6:00 am - 2:10 pm
MDW
-
OGG
13h 10m
2 stops
Southwest Logo
8:55 pm - 2:10 pm
OGG
-
MDW
12h 15m
2 stops
$524Southwest
Booking Insights

KAYAK's insights & trends for Midway to Maui flights

Get data-powered insights and trends into flights from Midway to Maui to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Chicago Midway Airport to Maui?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $380, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$221
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago Midway Airport to Kahului

FAQs - booking Maui flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Maui?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Maui.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Maui?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Maui is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Maui?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Maui with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Maui?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Maui up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Maui

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Maui. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Maui? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4318 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Everything you need to know for your flight to Maui

Information on your arrival and departure airports

Chicago Midway Airport (MDW)