$209 Find Cheap Flights from Chicago Midway Airport to Hawaii - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Midway to Hawaii

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Honolulu
Honolulu1 stop$557
Kahului
Kahului2 stops$607
Kailua-Kona
Kailua-Kona2 stops$544
Lihue
Lihue2 stops$435
Hilo
Hilo1 stop$642
Honolulu
Honolulu1 stop$557
Kahului
Kahului2 stops$607
Kailua-Kona
Kailua-Kona2 stops$544
Lihue
Lihue2 stops$435
Hilo
Hilo1 stop$642
Booking Insights

KAYAK's insights & trends for Midway to Hawaii flights

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

What is the cheapest month to fly from Chicago Midway Airport to Hawaii?

The cheapest month for flights from Chicago Midway Airport to Hawaii is September, when tickets cost $0 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $1,064 and $974 respectively.

Good to know

Low season

February

Cheapest flight

$209
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago Midway Airport to Honolulu

FAQs - booking Hawaii flights

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

    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 Hawaii.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Hawaii 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 Hawaii?

    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 Hawaii 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 Hawaii?

    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 Hawaii 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 Hawaii

 
Need help choosing which airline to fly with from Midway to Hawaii? 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.
7.9
SouthwestOverall score based on 4217 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.4Entertainment
7.0Food
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

More options for your flight from Midway to Hawaii

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