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Cheap flights from Hawaii to Chicago from $248

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hawaii to Chicago departing on 5/18. 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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Find the cheapest flights from Hawaii to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
10:10 am - 9:15 pm
MDW
-
HNL
16h 05m
1 stop
$554Southwest
Wed, Sep 9 - Sun, Sep 20
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
7:10 am - 9:10 pm
MDW
-
HNL
19h 00m
2 stops
$560Southwest
Wed, Sep 9 - Sun, Sep 20
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
6:10 am - 12:35 pm
MDW
-
HNL
11h 25m
1 stop
$584Southwest
Thu, Sep 10 - Sun, Sep 13
Southwest Logo
8:10 am - 11:45 pm
HNL
-
MDW
10h 35m
1 stop
Southwest Logo
10:20 am - 9:15 pm
MDW
-
HNL
15h 55m
2 stops
$590Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
8:15 am - 5:55 am
HNL
-
MDW
16h 40m
2 stops
Southwest Logo
7:10 am - 9:10 pm
MDW
-
HNL
19h 00m
2 stops
$595Southwest
Wed, Sep 9 - Sun, Sep 20
Southwest Logo
10:20 pm - 3:15 pm
HNL
-
MDW
11h 55m
2 stops
Southwest Logo
7:10 am - 9:10 pm
MDW
-
HNL
19h 00m
2 stops
$610Southwest
Thu, Sep 17 - Sun, Sep 20
Delta Logo
12:55 pm - 8:42 am
OGG
-
MDW
14h 47m
2 stops
Delta Logo
9:22 am - 7:35 pm
MDW
-
OGG
15h 13m
2 stops
$614Delta
Fri, May 29 - Sun, May 31
Southwest Logo
8:00 am - 4:30 am
HNL
-
MDW
15h 30m
2 stops
Southwest Logo
7:10 am - 9:10 pm
MDW
-
HNL
19h 00m
2 stops
$625Southwest
Thu, Sep 10 - Sun, Sep 13
Southwest Logo
9:25 pm - 5:05 pm
HNL
-
MDW
14h 40m
1 stop
Southwest Logo
10:50 am - 9:15 pm
MDW
-
HNL
15h 25m
1 stop
$630Southwest
Mon, Oct 26 - Thu, Oct 29
Delta Logo
12:55 pm - 8:42 am
OGG
-
MDW
14h 47m
2 stops
Delta Logo
9:22 am - 7:35 pm
MDW
-
OGG
15h 13m
2 stops
$644Delta
Fri, May 29 - Fri, Jun 5

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
Sep 9
HNL8:10 amHonolulu
15h 20m
1 stop
MDW4:30 amChicago Midway
Sep 20
MDW10:10 amChicago Midway
16h 05m
1 stop
HNL9:15 pmHonolulu
$554
Southwest
Sep 9
HNL8:10 amHonolulu
15h 20m
1 stop
MDW4:30 amChicago Midway
Sep 20
MDW7:10 amChicago Midway
19h 00m
2 stops
HNL9:10 pmHonolulu
$560
Southwest
Sep 10
HNL8:10 amHonolulu
15h 20m
1 stop
MDW4:30 amChicago Midway
Sep 13
MDW6:10 amChicago Midway
11h 25m
1 stop
HNL12:35 pmHonolulu
$584

Delta flights from Hawaii to Chicago Midway Airport

Our best Delta deals on Hawaii to Chicago Midway Airport flight tickets
Delta
May 29
OGG12:55 pmKahului
14h 47m
2 stops
MDW8:42 amChicago Midway
May 31
MDW9:22 amChicago Midway
15h 13m
2 stops
OGG7:35 pmKahului
$614
Delta
May 29
OGG12:55 pmKahului
14h 47m
2 stops
MDW8:42 amChicago Midway
Jun 5
MDW9:22 amChicago Midway
15h 13m
2 stops
OGG7:35 pmKahului
$644
Delta
May 29
OGG12:55 pmKahului
14h 47m
2 stops
MDW8:42 amChicago Midway
Jun 4
MDW6:23 amChicago Midway
18h 12m
2 stops
OGG7:35 pmKahului
$650

momondo Fare Finder

 
Customize your flight search to find flights from Hawaii to Chicago Midway Airport 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 May 12, 2026.
Use the filters below to find and compare flights from Hawaii to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/9

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 9/20

10:10 am-9:15 pm

1 stop16h 05m

$554

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/9

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 9/20

7:10 am-9:10 pm

2 stops19h 00m

$560

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/10

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 9/13

6:10 am-12:35 pm

1 stop11h 25m

$584
Quickest round-trip

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/10

8:10 am-11:45 pm

1 stop10h 35m

Chicago Midway

Mon 9/14

10:20 am-9:15 pm

2 stops15h 55m

$590

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/9

8:15 am-5:55 am

2 stops16h 40m

Chicago Midway

Sun 9/20

7:10 am-9:10 pm

2 stops19h 00m

$595

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/17

10:20 pm-3:15 pm

2 stops11h 55m

Chicago Midway

Sun 9/20

7:10 am-9:10 pm

2 stops19h 00m

$610

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 5/29

12:55 pm-8:42 am

2 stops14h 47m

Chicago Midway

Sun 5/31

9:22 am-7:35 pm

2 stops15h 13m

$614

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/10

8:00 am-4:30 am

2 stops15h 30m

Chicago Midway

Sun 9/13

7:10 am-9:10 pm

2 stops19h 00m

$625

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/26

9:25 pm-5:05 pm

1 stop14h 40m

Chicago Midway

Thu 10/29

10:50 am-9:15 pm

1 stop15h 25m

$630

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 5/29

12:55 pm-8:42 am

2 stops14h 47m

Chicago Midway

Fri 6/5

9:22 am-7:35 pm

2 stops15h 13m

$644

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 Chicago from

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

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

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

You could potentially save up to 5% on your flight if you consider stops on a Hawaii to Chicago Midway Airport flight.

Cheap Hawaii to Chicago Midway Airport flight deals and tips

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

Fastest flight time

10h 40m

Direct flights

None
The fastest flight from Hawaii to Chicago Midway Airport takes 10h 40m
There are no direct flights from Hawaii to Chicago Midway Airport. There are no popular flight routes from Hawaii to Chicago Midway Airport.
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Frequently asked questions about flying from Hawaii to Chicago Midway Airport

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

    Prices for flights from Hawaii to Chicago Midway Airport are refreshed on a daily basis.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Hawaii to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Hawaii to Chicago Midway Airport

Compare and see reviews for airlines that fly from Hawaii to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $581Free CancellationRating
8.0
4,295 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Hawaii.

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

momondo does allow users to show only those flights to Chicago from Hawaii which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Hawaii and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Hawaii and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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