What is the cheapest airline that flies from Chicago Midway to Hawaii?

Southwest and Delta are the most popular carriers operating from Chicago Midway to Hawaii

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?

As of October 2026, there is 1 operator available to choose from 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.

$222 Cheap Flights from Chicago Midway Airport to Hawaii in 2026/27

Find the cheapest flights from Chicago Midway Airport to Hawaii

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:29 am - 7:14 pmMDW Chicago Midway-LIH Lihue

14h 45m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

10:51 pm - 6:04 pmLIH Lihue-MDW Chicago Midway

15h 13m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

$435Delta

Sat, Oct 31 - Sun, Nov 8

9:30 am - 8:07 pmMDW Chicago Midway-LIH Lihue

14h 37m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

9:45 pm - 6:04 pmLIH Lihue-MDW Chicago Midway

16h 19m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

$455Delta

Wed, Nov 11 - Sun, Nov 15

9:29 am - 7:14 pmMDW Chicago Midway-LIH Lihue

14h 45m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

9:53 pm - 4:47 pmLIH Lihue-MDW Chicago Midway

13h 54m2 stops Seattle/Tacoma Intl Minneapolis St Paul

$455Delta

Thu, Oct 15 - Wed, Oct 28

5:50 am - 1:15 pmMDW Chicago Midway-LIH Lihue

11h 25m1 stop Las Vegas Harry Reid Intl

11:50 am - 5:55 amLIH Lihue-MDW Chicago Midway

14h 05m2 stops Honolulu Oakland

$493Southwest

Wed, Nov 4 - Wed, Nov 11

5:10 am - 12:35 pmMDW Chicago Midway-LIH Lihue

12h 25m1 stop Las Vegas Harry Reid Intl

4:05 pm - 11:35 amLIH Lihue-MDW Chicago Midway

15h 30m1 stop Oakland

$494Southwest

Thu, Oct 29 - Thu, Nov 5

5:10 am - 12:35 pmMDW Chicago Midway-LIH Lihue

12h 25m1 stop Las Vegas Harry Reid Intl

12:15 pm - 5:55 amLIH Lihue-MDW Chicago Midway

12h 40m1 stop Oakland

$494Southwest

Mon, Oct 19 - Mon, Oct 26

6:05 am - 12:35 pmMDW Chicago Midway-LIH Lihue

11h 30m1 stop Las Vegas Harry Reid Intl

12:15 pm - 5:55 amLIH Lihue-MDW Chicago Midway

12h 40m1 stop Oakland

$494Southwest

Wed, Oct 21 - Mon, Oct 26

9:50 am - 6:10 pmMDW Chicago Midway-LIH Lihue

13h 20m2 stops San Jose Honolulu

4:05 pm - 11:35 amLIH Lihue-MDW Chicago Midway

15h 30m1 stop Oakland

$500Southwest

Thu, Oct 29 - Thu, Nov 5

5:10 am - 12:35 pmMDW Chicago Midway-LIH Lihue

12h 25m1 stop Las Vegas Harry Reid Intl

11:50 am - 5:55 amLIH Lihue-MDW Chicago Midway

13h 05m2 stops Honolulu Oakland

$500Southwest

Mon, Oct 19 - Mon, Oct 26

6:05 am - 12:35 pmMDW Chicago Midway-LIH Lihue

11h 30m1 stop Las Vegas Harry Reid Intl

11:50 am - 5:55 amLIH Lihue-MDW Chicago Midway

13h 05m2 stops Honolulu Oakland

$500Southwest

Wed, Oct 21 - Mon, Oct 26

Cheap last minute flights

Enter your travel dates to find the best prices.

6:05 am - 12:35 pmMDW Chicago Midway-LIH Lihue

11h 30m1 stop Las Vegas Harry Reid Intl

12:15 pm - 5:55 amLIH Lihue-MDW Chicago Midway

12h 40m1 stop Oakland

$474Southwest

Tue, Oct 6 - Tue, Oct 13

6:05 am - 2:20 pmMDW Chicago Midway-LIH Lihue

13h 15m2 stops Las Vegas Harry Reid Intl Kahului

12:15 pm - 5:55 amLIH Lihue-MDW Chicago Midway

12h 40m1 stop Oakland

$481Southwest

Tue, Oct 6 - Tue, Oct 13

6:05 am - 2:20 pmMDW Chicago Midway-LIH Lihue

13h 15m2 stops Las Vegas Harry Reid Intl Kahului

8:30 pm - 2:05 pmLIH Lihue-MDW Chicago Midway

12h 35m2 stops Las Vegas Harry Reid Intl Denver Intl

$586Southwest

Tue, Oct 6 - Tue, Oct 13

6:05 am - 1:28 pmMDW Chicago Midway-HNL Honolulu

12h 23m1 stop Atlanta Hartsfield-Jackson

2:51 pm - 9:32 amHNL Honolulu-MDW Chicago Midway

13h 41m1 stop Detroit Metropolitan Wayne County

$670Delta

Sat, Oct 3 - Sat, Oct 17

6:04 am - 1:36 pmMDW Chicago Midway-HNL Honolulu

12h 32m1 stop Atlanta Hartsfield-Jackson

2:51 pm - 9:32 amHNL Honolulu-MDW Chicago Midway

13h 41m1 stop Detroit Metropolitan Wayne County

$670Delta

Wed, Oct 7 - Sun, Oct 11

5:45 am - 1:15 pmMDW Chicago Midway-HNL Honolulu

12h 30m1 stop Phoenix Sky Harbor Intl

8:15 am - 5:00 amHNL Honolulu-MDW Chicago Midway

15h 45m1 stop San Jose

$670Southwest

Tue, Oct 6 - Thu, Oct 8

5:20 am - 1:25 pmMDW Chicago Midway-HNL Honolulu

13h 05m1 stop Las Vegas Harry Reid Intl

8:10 am - 4:30 amHNL Honolulu-MDW Chicago Midway

15h 20m1 stop San Diego

$670Southwest

Sun, Oct 4 - Tue, Oct 6

5:25 am - 12:40 pmMDW Chicago Midway-HNL Honolulu

12h 15m1 stop San Diego

8:10 am - 4:30 amHNL Honolulu-MDW Chicago Midway

15h 20m1 stop San Diego

$670Southwest

Mon, Oct 5 - Wed, Oct 7

5:45 am - 12:55 pmMDW Chicago Midway-OGG Kahului

12h 10m1 stop Phoenix Sky Harbor Intl

10:00 am - 5:55 amOGG Kahului-MDW Chicago Midway

14h 55m1 stop Oakland

$670Southwest

Wed, Oct 7 - Tue, Oct 13

6:04 am - 1:36 pmMDW Chicago Midway-HNL Honolulu

12h 32m1 stop Atlanta Hartsfield-Jackson

3:30 pm - 10:03 amHNL Honolulu-MDW Chicago Midway

13h 33m1 stop Atlanta Hartsfield-Jackson

$670Delta

Tue, Oct 6 - Tue, Oct 13

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Delta flights from Chicago Midway Airport to Hawaii

Our best Delta deals on Chicago Midway Airport to Hawaii flight tickets

Delta

Oct 15

MDW9:29 amChicago Midway

14h 45m

2 stops

LIH7:14 pmLihue

Oct 28

LIH9:53 pmLihue

13h 54m

2 stops

MDW4:47 pmChicago Midway

$455

Delta

Nov 7

MDW4:19 pmChicago Midway

23h 45m

2 stops

HNL12:04 pmHonolulu

Nov 11

HNL1:35 pmHonolulu

16h 11m

2 stops

MDW9:46 amChicago Midway

$560

Delta

Nov 11

MDW9:30 amChicago Midway

14h 37m

2 stops

LIH8:07 pmLihue

Nov 15

LIH9:45 pmLihue

16h 19m

2 stops

MDW6:04 pmChicago Midway

$570

Southwest flights from Chicago Midway Airport to Hawaii

Our best Southwest deals on Chicago Midway Airport to Hawaii flight tickets

Southwest

Oct 6

MDW6:05 amChicago Midway

11h 30m

1 stop

LIH12:35 pmLihue

Oct 13

LIH12:15 pmLihue

12h 40m

1 stop

MDW5:55 amChicago Midway

$474

Southwest

Oct 6

MDW6:05 amChicago Midway

13h 15m

2 stops

LIH2:20 pmLihue

Oct 13

LIH12:15 pmLihue

12h 40m

1 stop

MDW5:55 amChicago Midway

$481

Southwest

Nov 4

MDW5:50 amChicago Midway

11h 25m

1 stop

LIH1:15 pmLihue

Nov 11

LIH11:50 amLihue

14h 05m

2 stops

MDW5:55 amChicago Midway

$493

momondo Fare Finder

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

Cheapest round-trip

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Sat 10/31

9:29 am-7:14 pm

2 stops14h 45m

Lihue

Sun 11/8

10:51 pm-6:04 pm

2 stops15h 13m

$435

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Wed 11/11

9:30 am-8:07 pm

2 stops14h 37m

Lihue

Sun 11/15

9:45 pm-6:04 pm

2 stops16h 19m

$455

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Thu 10/15

9:29 am-7:14 pm

2 stops14h 45m

Lihue

Wed 10/28

9:53 pm-4:47 pm

2 stops13h 54m

$455

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Wed 11/4

5:50 am-1:15 pm

1 stop11h 25m

Lihue

Wed 11/11

11:50 am-5:55 am

2 stops14h 05m

$493

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Thu 10/29

5:10 am-12:35 pm

1 stop12h 25m

Lihue

Thu 11/5

4:05 pm-11:35 am

1 stop15h 30m

$494

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Mon 10/19

5:10 am-12:35 pm

1 stop12h 25m

Lihue

Mon 10/26

12:15 pm-5:55 am

1 stop12h 40m

$494

Quickest round-trip

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Wed 10/21

6:05 am-12:35 pm

1 stop11h 30m

Lihue

Mon 10/26

12:15 pm-5:55 am

1 stop12h 40m

$494

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Thu 10/29

9:50 am-6:10 pm

2 stops13h 20m

Lihue

Thu 11/5

4:05 pm-11:35 am

1 stop15h 30m

$500

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Mon 10/19

5:10 am-12:35 pm

1 stop12h 25m

Lihue

Mon 10/26

11:50 am-5:55 am

2 stops13h 05m

$500

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Wed 10/21

6:05 am-12:35 pm

1 stop11h 30m

Lihue

Mon 10/26

11:50 am-5:55 am

2 stops13h 05m

$500

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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 $654.

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

You could potentially save up to 35% 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	$222
Fastest flight time	11h 10m
Direct flights	None

The best one-way flight to Hawaii from Chicago Midway Airport in the past 72 hours is $222. The best round-trip flight deal from Chicago Midway Airport to Hawaii found on momondo in the last 72 hours is $435.

The fastest flight from Chicago Midway Airport to Hawaii takes 11h 10m

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

Frequently asked questions about flying from Chicago Midway Airport to Hawaii

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?
As of October 2026, there is 1 operator available to choose from 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
Southwest	PriceFrom $556	Free Cancellation	Rating 8.0 4,212 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.