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Cheap flights from Chicago Midway Airport to Hawaii from $227

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Hawaii departing on 12/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Hawaii

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 3:37 pmMDW-OGG
13h 37m1 stop
Delta Logo
5:10 pm - 9:58 amOGG-MDW
12h 48m1 stop
$461Delta
Find Deal
Thu, Jan 29 - Thu, Feb 5
Delta Logo
9:30 am - 8:31 pmMDW-LIH
15h 01m2 stops
Delta Logo
9:45 pm - 6:34 pmLIH-MDW
15h 49m2 stops
$464Delta
Find Deal
Tue, Feb 24 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pmMDW-OGG
13h 37m1 stop
Delta Logo
5:10 pm - 12:48 pmOGG-MDW
15h 38m2 stops
$466Delta
Find Deal
Thu, Jan 29 - Thu, Feb 5
Delta Logo
9:34 am - 7:15 pmMDW-OGG
13h 41m2 stops
Delta Logo
9:05 pm - 4:31 pmOGG-MDW
15h 26m2 stops
$472Delta
Find Deal
Wed, Jan 7 - Tue, Jan 13
Delta Logo
6:00 am - 3:30 pmMDW-OGG
13h 30m1 stop
Delta Logo
4:00 pm - 9:56 amOGG-MDW
12h 56m1 stop
$492Delta
Find Deal
Mon, Feb 23 - Tue, Mar 10
Southwest Logo
5:10 am - 6:10 pmMDW-KOA
17h 00m2 stops
Southwest Logo
9:15 pm - 1:40 pmKOA-MDW
12h 25m1 stop
$539Southwest
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Mon, Dec 1 - Tue, Dec 9
Southwest Logo
11:15 am - 9:00 pmMDW-HNL
13h 45m1 stop
Southwest Logo
9:25 pm - 4:20 pmHNL-MDW
14h 55m2 stops
$542Southwest
Find Deal
Sun, Dec 7 - Thu, Dec 11
Southwest Logo
5:05 am - 12:50 pmMDW-OGG
11h 45m1 stop
Southwest Logo
9:35 pm - 12:35 pmOGG-MDW
11h 00m1 stop
$543Southwest
Find Deal
Tue, Jan 20 - Tue, Jan 27
Southwest Logo
5:05 am - 12:50 pmMDW-OGG
11h 45m1 stop
Southwest Logo
7:00 pm - 12:35 pmOGG-MDW
13h 35m2 stops
$548Southwest
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Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
12:18 pm - 11:00 amMDW-HNL
26h 42m2 stops
Multiple Airlines Logo
10:10 am - 6:23 pmHNL-MDW
28h 13m1 stop
$565Multiple Airlines
Find Deal
Mon, Dec 8 - Sat, Dec 13

Southwest flights from Chicago Midway Airport to Hawaii

Our best Southwest deals on Chicago Midway Airport to Hawaii flight tickets
Southwest
Dec 1
MDW5:10 amChicago Midway
17h 00m
2 stops
KOA6:10 pmKona Intl
Dec 9
KOA9:15 pmKona Intl
12h 25m
1 stop
MDW1:40 pmChicago Midway
$539
Find similar
Southwest
Dec 7
MDW11:15 amChicago Midway
13h 45m
1 stop
HNL9:00 pmHonolulu
Dec 11
HNL9:25 pmHonolulu
14h 55m
2 stops
MDW4:20 pmChicago Midway
$542
Find similar
Southwest
Jan 20
MDW5:05 amChicago Midway
11h 45m
1 stop
OGG12:50 pmKahului
Jan 27
OGG9:35 pmKahului
11h 00m
1 stop
MDW12:35 pmChicago Midway
$543
Find similar

Delta flights from Chicago Midway Airport to Hawaii

Our best Delta deals on Chicago Midway Airport to Hawaii flight tickets
Delta
Jan 29
MDW6:00 amChicago Midway
13h 37m
1 stop
OGG3:37 pmKahului
Feb 5
OGG5:10 pmKahului
12h 48m
1 stop
MDW9:58 amChicago Midway
$461
Find similar
Delta
Feb 24
MDW9:30 amChicago Midway
15h 01m
2 stops
LIH8:31 pmLihue
Mar 10
LIH9:45 pmLihue
15h 49m
2 stops
MDW6:34 pmChicago Midway
$464
Find similar
Delta
Jan 29
MDW6:00 amChicago Midway
13h 37m
1 stop
OGG3:37 pmKahului
Feb 5
OGG5:10 pmKahului
15h 38m
2 stops
MDW12:48 pmChicago Midway
$466
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Hawaii that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 2, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Hawaii that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/29

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 2/5

5:10 pm-9:58 am

1 stop12h 48m

$461

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/24

9:30 am-8:31 pm

2 stops15h 01m

Lihue

Tue 3/10

9:45 pm-6:34 pm

2 stops15h 49m

$464

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/29

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 2/5

5:10 pm-12:48 pm

2 stops15h 38m

$466

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 1/7

9:34 am-7:15 pm

2 stops13h 41m

Kahului

Tue 1/13

9:05 pm-4:31 pm

2 stops15h 26m

$472

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/23

6:00 am-3:30 pm

1 stop13h 30m

Kahului

Tue 3/10

4:00 pm-9:56 am

1 stop12h 56m

$492

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 12/1

5:10 am-6:10 pm

2 stops17h 00m

Kona Intl

Tue 12/9

9:15 pm-1:40 pm

1 stop12h 25m

$539

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 12/7

11:15 am-9:00 pm

1 stop13h 45m

Honolulu

Thu 12/11

9:25 pm-4:20 pm

2 stops14h 55m

$542

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 1/20

5:05 am-12:50 pm

1 stop11h 45m

Kahului

Tue 1/27

9:35 pm-12:35 pm

1 stop11h 00m

$543

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 1/20

5:05 am-12:50 pm

1 stop11h 45m

Kahului

Tue 1/27

7:00 pm-12:35 pm

2 stops13h 35m

$548

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 12/8

12:18 pm-11:00 am

2 stops26h 42m

Honolulu

Sat 12/13

10:10 am-6:23 pm

1 stop28h 13m

$565

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Hawaii from

How to get the cheapest flight ticket from Chicago Midway Airport to Hawaii

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Hawaii?

If you don’t want to visit Hawaii in January, then you should wait until February to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $617.

What is the cheapest day to depart on your flight to Hawaii?

On average, the least expensive day to fly to Hawaii from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $667. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to Hawaii on a Saturday will generally be more expensive and average around $1,092. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Hawaii?

Our data shows that the cheapest Chicago Midway Airport to Hawaii flights are usually those with departure times in the morning. Our users have found flights to Hawaii in the morning for as low as $775. Flights in the evening are often more expensive with an average ticket price of $782.

Can stopping save me money on Chicago Midway Airport to Hawaii flights?

You could potentially save up to 1% on your flight if you consider stops on a Chicago Midway Airport to Hawaii flight.

Cheap Chicago Midway Airport to Hawaii flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Hawaii

Direct flights

None
There are no direct flights from Chicago Midway Airport to Hawaii. There are no popular flight routes from Chicago Midway Airport to Hawaii.
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Hawaii?

    Prices for flights from Chicago Midway Airport to Hawaii refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Hawaii?

  • How old do you have to be to fly from Chicago Midway Airport to Hawaii?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Hawaii.

  • What documentation or ID do you need to fly to Hawaii?

    The travel and health documents required for your trip to Hawaii can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hawaii. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago Midway Airport to Hawaii

Compare and see reviews for airlines that fly from Chicago Midway Airport to Hawaii with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $442Free CancellationRating
7.9
8,001 reviews
Search Delta flights
SouthwestPriceFrom $479Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Hawaii?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Hawaii for you.

Can I find flights from Chicago to Hawaii with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Hawaii flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Hawaii?

momondo provides multiple filters to help you find the best flight to Hawaii from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Hawaii right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Hawaii flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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