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Cheap flights from Chicago Midway Airport to Hawaii from $211

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 4/15. 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.
Southwest Logo
8:25 am - 4:30 pm
MDW
-
HNL
12h 05m
1 stop
Southwest Logo
9:10 am - 4:35 am
HNL
-
MDW
15h 25m
1 stop
$413Southwest
Wed, Feb 25 - Fri, Mar 6
Southwest Logo
7:55 am - 4:30 pm
MDW
-
HNL
12h 35m
1 stop
Southwest Logo
9:30 pm - 2:45 pm
HNL
-
MDW
13h 15m
2 stops
$419Southwest
Mon, Feb 23 - Tue, Feb 24
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
Southwest Logo
8:00 am - 9:00 pm
MDW
-
HNL
17h 00m
1 stop
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
$422Southwest
Mon, Mar 2 - Tue, Mar 17
Southwest Logo
8:05 am - 9:00 pm
MDW
-
HNL
16h 55m
2 stops
Southwest Logo
9:05 pm - 3:50 pm
HNL
-
MDW
13h 45m
2 stops
$424Southwest
Mon, Mar 2 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
10:00 pm - 6:40 pm
OGG
-
MDW
16h 40m
2 stops
$428Delta
Sun, Mar 1 - Thu, Mar 5
Southwest Logo
8:50 am - 10:10 pm
MDW
-
HNL
17h 20m
1 stop
Southwest Logo
9:05 pm - 6:00 pm
HNL
-
MDW
15h 55m
2 stops
$428Southwest
Thu, Mar 5 - Wed, Mar 11
Delta Logo
9:31 am - 9:45 pm
MDW
-
HNL
17h 14m
2 stops
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
$430Delta
Mon, Apr 13 - Fri, Apr 17
Southwest Logo
10:10 am - 9:05 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
11:55 am - 5:25 am
HNL
-
MDW
12h 30m
1 stop
$431Southwest
Wed, Apr 8 - Fri, Apr 17
Delta Logo
6:00 am - 7:15 pm
MDW
-
OGG
17h 15m
2 stops
Delta Logo
4:00 pm - 12:29 pm
OGG
-
MDW
15h 29m
2 stops
$433Delta
Tue, Mar 3 - Tue, Mar 10

Southwest flights from Chicago Midway Airport to Hawaii

Our best Southwest deals on Chicago Midway Airport to Hawaii flight tickets
Southwest
Feb 25
MDW8:25 amChicago Midway
12h 05m
1 stop
HNL4:30 pmHonolulu
Mar 6
HNL9:10 amHonolulu
15h 25m
1 stop
MDW4:35 amChicago Midway
$413
Southwest
Apr 27
MDW9:45 pmChicago Midway
17h 05m
1 stop
HNL9:50 amHonolulu
May 6
HNL9:05 pmHonolulu
15h 50m
2 stops
MDW5:55 pmChicago Midway
$419
Southwest
Mar 2
MDW7:55 amChicago Midway
12h 35m
1 stop
HNL4:30 pmHonolulu
Mar 9
HNL11:15 amHonolulu
13h 05m
1 stop
MDW5:20 amChicago Midway
$422

Delta flights from Chicago Midway Airport to Hawaii

Our best Delta deals on Chicago Midway Airport to Hawaii flight tickets
Delta
Feb 23
MDW6:00 amChicago Midway
13h 37m
1 stop
OGG3:37 pmKahului
Mar 10
OGG4:00 pmKahului
12h 56m
1 stop
MDW9:56 amChicago Midway
$422
Delta
Mar 2
MDW6:00 amChicago Midway
13h 11m
1 stop
HNL3:11 pmHonolulu
Mar 10
HNL3:46 pmHonolulu
12h 07m
1 stop
MDW8:53 amChicago Midway
$424
Delta
Mar 1
MDW6:00 amChicago Midway
13h 37m
1 stop
OGG3:37 pmKahului
Mar 4
OGG1:53 pmKahului
15h 13m
2 stops
MDW9:06 amChicago Midway
$428

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 February 4, 2026.
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

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 2/25

8:25 am-4:30 pm

1 stop12h 05m

Honolulu

Fri 3/6

9:10 am-4:35 am

1 stop15h 25m

$413

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 2/23

7:55 am-4:30 pm

1 stop12h 35m

Honolulu

Tue 2/24

9:30 pm-2:45 pm

2 stops13h 15m

$419

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/23

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Tue 3/10

4:00 pm-9:56 am

1 stop12h 56m

$422

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 3/2

8:00 am-9:00 pm

1 stop17h 00m

Honolulu

Tue 3/17

8:15 am-5:00 am

1 stop15h 45m

$422

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 3/2

8:05 am-9:00 pm

2 stops16h 55m

Honolulu

Tue 3/10

9:05 pm-3:50 pm

2 stops13h 45m

$424

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 3/1

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 3/5

10:00 pm-6:40 pm

2 stops16h 40m

$428

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 3/5

8:50 am-10:10 pm

1 stop17h 20m

Honolulu

Wed 3/11

9:05 pm-6:00 pm

2 stops15h 55m

$428

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 4/13

9:31 am-9:45 pm

2 stops17h 14m

Honolulu

Fri 4/17

3:15 pm-8:47 am

1 stop12h 32m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 4/8

10:10 am-9:05 pm

1 stop15h 55m

Honolulu

Fri 4/17

11:55 am-5:25 am

1 stop12h 30m

$431

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 3/3

6:00 am-7:15 pm

2 stops17h 15m

Kahului

Tue 3/10

4:00 pm-12:29 pm

2 stops15h 29m

$433

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 April to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $620.

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

You could potentially save up to 21% 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

Fastest flight time

10h 55m

Direct flights

None
The fastest flight from Chicago Midway Airport to Hawaii takes 10h 55m
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 $429Free CancellationRating
7.9
8,144 reviews
Search Delta flights
SouthwestPriceFrom $468Free CancellationRating
8.0
4,274 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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