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Cheap flights from Hawaii to Chicago 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 Hawaii to Chicago departing on 1/22. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:00 pm - 6:36 pm
OGG
-
MDW
16h 36m2 stops
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
$417Delta
Thu, Jan 22 - Mon, Feb 2
Delta Logo
5:10 pm - 9:53 am
OGG
-
MDW
12h 43m1 stop
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
$421Delta
Thu, Jan 29 - Sun, Feb 8
Delta Logo
9:05 pm - 5:55 pm
OGG
-
MDW
16h 50m2 stops
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
$426Delta
Wed, Jan 21 - Mon, Feb 2
Delta Logo
5:15 pm - 9:08 am
HNL
-
MDW
11h 53m1 stop
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m1 stop
$427Delta
Thu, Jan 22 - Thu, Jan 29
Delta Logo
4:50 pm - 9:53 am
HNL
-
MDW
13h 03m1 stop
Delta Logo
9:32 am - 9:28 pm
MDW
-
HNL
15h 56m2 stops
$429Delta
Wed, Jan 28 - Wed, Feb 4
Delta Logo
5:10 pm - 9:53 am
OGG
-
MDW
12h 43m1 stop
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
$433Delta
Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
10:15 am - 9:08 pm
HNL
-
MDW
30h 53m2 stops
Multiple Airlines Logo
3:21 pm - 11:15 am
MDW
-
HNL
23h 54m1 stop
$524Multiple Airlines
Fri, Feb 13 - Sun, Feb 22
Southwest Logo
8:10 pm - 1:10 pm
LIH
-
MDW
12h 00m1 stop
Southwest Logo
6:10 am - 1:10 pm
MDW
-
LIH
12h 00m1 stop
$653Southwest
Thu, May 14 - Tue, May 19
Southwest Logo
8:10 pm - 4:15 pm
LIH
-
MDW
15h 05m1 stop
Southwest Logo
7:55 am - 4:10 pm
MDW
-
LIH
13h 15m2 stops
$658Southwest
Thu, May 14 - Tue, May 19
Southwest Logo
8:10 pm - 1:45 pm
LIH
-
MDW
12h 35m2 stops
Southwest Logo
6:10 am - 4:10 pm
MDW
-
LIH
15h 00m2 stops
$664Southwest
Thu, May 14 - Tue, May 19

Delta flights from Hawaii to Chicago Midway Airport

Our best Delta deals on Hawaii to Chicago Midway Airport flight tickets
Delta
Jan 22
OGG10:00 pmKahului
16h 36m
2 stops
MDW6:36 pmChicago Midway
Feb 2
MDW6:00 amChicago Midway
13h 37m
1 stop
OGG3:37 pmKahului
$417
Find similar
Delta
Jan 29
OGG5:10 pmKahului
12h 43m
1 stop
MDW9:53 amChicago Midway
Feb 8
MDW6:00 amChicago Midway
13h 37m
1 stop
OGG3:37 pmKahului
$421
Find similar
Delta
Jan 21
OGG9:05 pmKahului
16h 50m
2 stops
MDW5:55 pmChicago Midway
Feb 2
MDW6:00 amChicago Midway
13h 37m
1 stop
OGG3:37 pmKahului
$426
Find similar

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
May 14
LIH8:10 pmLihue
12h 00m
1 stop
MDW1:10 pmChicago Midway
May 19
MDW6:10 amChicago Midway
12h 00m
1 stop
LIH1:10 pmLihue
$653
Find similar
Southwest
May 14
LIH8:10 pmLihue
15h 05m
1 stop
MDW4:15 pmChicago Midway
May 19
MDW7:55 amChicago Midway
13h 15m
2 stops
LIH4:10 pmLihue
$658
Find similar
Southwest
Jan 27
OGG9:25 pmKahului
13h 20m
1 stop
MDW2:45 pmChicago Midway
Feb 5
MDW8:10 amChicago Midway
12h 15m
1 stop
OGG4:25 pmKahului
$663
Find similar

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 December 22, 2025.
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

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 1/22

10:00 pm-6:36 pm

2 stops16h 36m

Chicago Midway

Mon 2/2

6:00 am-3:37 pm

1 stop13h 37m

$417

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 1/29

5:10 pm-9:53 am

1 stop12h 43m

Chicago Midway

Sun 2/8

6:00 am-3:37 pm

1 stop13h 37m

$421

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 1/21

9:05 pm-5:55 pm

2 stops16h 50m

Chicago Midway

Mon 2/2

6:00 am-3:37 pm

1 stop13h 37m

$426

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 1/22

5:15 pm-9:08 am

1 stop11h 53m

Chicago Midway

Thu 1/29

6:00 am-3:10 pm

1 stop13h 10m

$427

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

4:50 pm-9:53 am

1 stop13h 03m

Chicago Midway

Wed 2/4

9:32 am-9:28 pm

2 stops15h 56m

$429

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 1/26

5:10 pm-9:53 am

1 stop12h 43m

Chicago Midway

Mon 2/2

6:00 am-3:37 pm

1 stop13h 37m

$433

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 2/13

10:15 am-9:08 pm

2 stops30h 53m

Chicago Midway

Sun 2/22

3:21 pm-11:15 am

1 stop23h 54m

$524

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 5/14

8:10 pm-1:10 pm

1 stop12h 00m

Chicago Midway

Tue 5/19

6:10 am-1:10 pm

1 stop12h 00m

$653

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 5/14

8:10 pm-4:15 pm

1 stop15h 05m

Chicago Midway

Tue 5/19

7:55 am-4:10 pm

2 stops13h 15m

$658

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 5/14

8:10 pm-1:45 pm

2 stops12h 35m

Chicago Midway

Tue 5/19

6:10 am-4:10 pm

2 stops15h 00m

$664

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

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Hawaii. The lowest ticket price found for a Tuesday departure recently was $617. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from Hawaii because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,096.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Hawaii at noon is the least expensive time of day to depart. momondo users have found prices as low as $591 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $972. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You could potentially save up to 7% 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

11h 53m

Direct flights

None
The fastest flight from Hawaii to Chicago Midway Airport takes 11h 53m
There are no direct flights from Hawaii to Chicago Midway Airport. There are no popular flight routes from Hawaii to Chicago Midway Airport.
Search flight deals

  • 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
4,254 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
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

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