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Cheap flights from Chicago Midway Airport to Hawaii from $212

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 9/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Hawaii

Cheap round-trip flights

Southwest Logo
8:25 am - 9:00 pmMDW-HNL
17h 35m1 stop
Southwest Logo
8:05 am - 12:30 amHNL-MDW
11h 25m1 stop
$416Southwest
Find Deal
Sat, Sep 13 - Thu, Sep 18
Delta Logo
6:00 am - 1:15 pmMDW-HNL
12h 15m1 stop
Delta Logo
3:00 pm - 8:35 amHNL-MDW
12h 35m1 stop
$423Delta
Find Deal
Mon, Aug 25 - Thu, Sep 4
Delta Logo
6:00 am - 1:15 pmMDW-HNL
12h 15m1 stop
Delta Logo
1:20 pm - 8:50 amHNL-MDW
14h 30m2 stops
$428Delta
Find Deal
Mon, Aug 25 - Thu, Sep 4
Delta Logo
6:00 am - 1:15 pmMDW-HNL
12h 15m1 stop
Delta Logo
1:00 pm - 8:53 amHNL-MDW
14h 53m2 stops
$429Delta
Find Deal
Sat, Sep 6 - Tue, Sep 16
Delta Logo
9:30 am - 8:20 pmMDW-HNL
14h 50m2 stops
Delta Logo
1:35 pm - 8:46 amHNL-MDW
15h 11m2 stops
$434Delta
Find Deal
Thu, Nov 13 - Mon, Nov 17
Southwest Logo
8:20 am - 4:30 pmMDW-OGG
13h 10m1 stop
Southwest Logo
8:25 pm - 2:05 pmOGG-MDW
12h 40m1 stop
$454Southwest
Find Deal
Sun, Sep 28 - Mon, Oct 6
Southwest Logo
7:40 am - 9:00 pmMDW-HNL
18h 20m1 stop
Southwest Logo
8:05 am - 12:30 amHNL-MDW
11h 25m1 stop
$456Southwest
Find Deal
Fri, Sep 12 - Thu, Sep 18
Southwest Logo
8:20 am - 6:15 pmMDW-OGG
14h 55m2 stops
Southwest Logo
8:25 pm - 2:05 pmOGG-MDW
12h 40m1 stop
$459Southwest
Find Deal
Sun, Sep 28 - Mon, Oct 6
Southwest Logo
12:10 pm - 9:00 pmMDW-HNL
13h 50m1 stop
Southwest Logo
9:05 pm - 1:25 pmHNL-MDW
11h 20m1 stop
$461Southwest
Find Deal
Fri, Sep 5 - Wed, Sep 10
Delta Logo
9:15 am - 8:28 pmMDW-HNL
16h 13m2 stops
Delta Logo
1:20 pm - 8:50 amHNL-MDW
14h 30m2 stops
$474Delta
Find Deal
Mon, Aug 25 - Thu, Sep 4

Southwest flights from Chicago Midway Airport to Hawaii

Our best Southwest deals on Chicago Midway Airport to Hawaii flight tickets
Southwest
Sep 13
MDW8:25 amChicago Midway
17h 35m
1 stop
HNL9:00 pmHonolulu
Sep 18
HNL8:05 amHonolulu
11h 25m
1 stop
MDW12:30 amChicago Midway
$416
Find similar
Southwest
Sep 28
MDW8:20 amChicago Midway
13h 10m
1 stop
OGG4:30 pmKahului
Oct 6
OGG8:25 pmKahului
12h 40m
1 stop
MDW2:05 pmChicago Midway
$454
Find similar
Southwest
Sep 12
MDW7:40 amChicago Midway
18h 20m
1 stop
HNL9:00 pmHonolulu
Sep 18
HNL8:05 amHonolulu
11h 25m
1 stop
MDW12:30 amChicago Midway
$456
Find similar

Delta flights from Chicago Midway Airport to Hawaii

Our best Delta deals on Chicago Midway Airport to Hawaii flight tickets
Delta
Aug 25
MDW6:00 amChicago Midway
12h 15m
1 stop
HNL1:15 pmHonolulu
Sep 4
HNL3:00 pmHonolulu
12h 35m
1 stop
MDW8:35 amChicago Midway
$423
Find similar
Delta
Aug 25
MDW6:00 amChicago Midway
12h 15m
1 stop
HNL1:15 pmHonolulu
Sep 4
HNL1:20 pmHonolulu
14h 30m
2 stops
MDW8:50 amChicago Midway
$428
Find similar
Delta
Sep 6
MDW6:00 amChicago Midway
12h 15m
1 stop
HNL1:15 pmHonolulu
Sep 16
HNL1:00 pmHonolulu
14h 53m
2 stops
MDW8:53 amChicago Midway
$429
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 August 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

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 9/13

8:25 am-9:00 pm

1 stop17h 35m

Honolulu

Thu 9/18

8:05 am-12:30 am

1 stop11h 25m

$416

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 8/25

6:00 am-1:15 pm

1 stop12h 15m

Honolulu

Thu 9/4

3:00 pm-8:35 am

1 stop12h 35m

$423

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 8/25

6:00 am-1:15 pm

1 stop12h 15m

Honolulu

Thu 9/4

1:20 pm-8:50 am

2 stops14h 30m

$428

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 9/6

6:00 am-1:15 pm

1 stop12h 15m

Honolulu

Tue 9/16

1:00 pm-8:53 am

2 stops14h 53m

$429

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 11/13

9:30 am-8:20 pm

2 stops14h 50m

Honolulu

Mon 11/17

1:35 pm-8:46 am

2 stops15h 11m

$434

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 9/28

8:20 am-4:30 pm

1 stop13h 10m

Kahului

Mon 10/6

8:25 pm-2:05 pm

1 stop12h 40m

$454

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 9/12

7:40 am-9:00 pm

1 stop18h 20m

Honolulu

Thu 9/18

8:05 am-12:30 am

1 stop11h 25m

$456

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 9/28

8:20 am-6:15 pm

2 stops14h 55m

Kahului

Mon 10/6

8:25 pm-2:05 pm

1 stop12h 40m

$459

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 9/5

12:10 pm-9:00 pm

1 stop13h 50m

Honolulu

Wed 9/10

9:05 pm-1:25 pm

1 stop11h 20m

$461

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 8/25

9:15 am-8:28 pm

2 stops16h 13m

Honolulu

Thu 9/4

1:20 pm-8:50 am

2 stops14h 30m

$474

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 February, then you should wait until January to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $612.

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 9% 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

Best Price Found

$212

Fastest flight time

10h 55m

Direct flights

None

Airports in Hawaii

5 airports
The best one-way flight to Hawaii from Chicago Midway Airport in the past 72 hours is $212. The best round-trip flight deal from Chicago Midway Airport to Hawaii found on momondo in the last 72 hours is $416.
The fastest flight from Chicago Midway Airport to Hawaii takes 10h 55m
There are no direct flights from Chicago Midway Airport to Hawaii. Popular non-direct routes for this connection are Chicago Midway Airport - Kahului Airport, Chicago Midway Airport - Lihue Airport and Chicago Midway Airport - Honolulu Airport.
There are 5 airports near Hawaii: Hilo Intl (ITO), Honolulu (HNL), Lihue (LIH), Kona Intl (KOA), Kahului (OGG)
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  • 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 $427Free CancellationRating
8.0
7,985 reviews
Search Delta flights
SouthwestPriceFrom $498Free CancellationRating
8.0
4,246 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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