$185 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 3/2. 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
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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

Mon, Feb 23 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
4:00 pm - 9:56 am
OGG
-
MDW
12h 56m
1 stop
$422Delta
Mon, Feb 23 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
12:59 pm - 8:50 am
OGG
-
MDW
14h 51m
2 stops
$428Delta
Mon, Feb 23 - Tue, Mar 10
Delta Logo
9:34 am - 7:15 pm
MDW
-
OGG
13h 41m
2 stops
Delta Logo
12:59 pm - 8:53 am
OGG
-
MDW
14h 54m
2 stops
$433Delta
Mon, Feb 23 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
4:00 pm - 9:56 am
OGG
-
MDW
12h 56m
1 stop
$442Delta
Thu, Mar 5 - Thu, Mar 12
Southwest Logo
6:05 am - 1:35 pm
MDW
-
OGG
11h 30m
1 stop
Southwest Logo
8:55 pm - 6:05 pm
OGG
-
MDW
16h 10m
1 stop
$445Southwest
Mon, Feb 23 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
12:59 pm - 8:50 am
OGG
-
MDW
14h 51m
2 stops
$448Delta
Mon, Feb 23 - Tue, Mar 10
Delta Logo
9:34 am - 7:15 pm
MDW
-
OGG
13h 41m
2 stops
Delta Logo
12:59 pm - 8:53 am
OGG
-
MDW
14h 54m
2 stops
$453Delta
Tue, Mar 17 - Tue, Mar 31
Delta Logo
5:40 pm - 11:30 am
MDW
-
OGG
22h 50m
2 stops
Delta Logo
4:45 pm - 9:56 am
OGG
-
MDW
12h 11m
1 stop
$458Delta
Thu, Feb 26 - Thu, Mar 5
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
5:10 pm - 9:54 am
OGG
-
MDW
12h 44m
1 stop
$465Delta
Thu, Feb 26 - Thu, Mar 5
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
5:10 pm - 12:46 pm
OGG
-
MDW
15h 36m
2 stops
$471Delta
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 $388, prices are generally cheapest when you fly direct.

Good to know

Low seasonAugust
Cheapest flight$185
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 20% 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 4256 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

10.0 ExcellentManetta, Jan 2026
MDW - CLT
Read more Southwest reviews

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Everything you need to know for your flight to Maui

Information on your arrival and departure airports