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Cheap flights from Hawaii to Chicago from $217

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 11/11. 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

Delta Logo
4:45 pm - 8:40 amHNL-MDW
10h 55m1 stop
Delta Logo
6:00 am - 3:02 pmMDW-HNL
13h 02m1 stop
$465Delta
Find Deal
Mon, Oct 27 - Mon, Nov 10
Delta Logo
1:15 pm - 10:30 amHNL-MDW
16h 15m2 stops
Delta Logo
6:00 am - 3:02 pmMDW-HNL
13h 02m1 stop
$470Delta
Find Deal
Fri, Oct 24 - Mon, Nov 10
Delta Logo
10:31 pm - 5:43 pmHNL-MDW
14h 12m2 stops
Delta Logo
6:00 am - 3:02 pmMDW-HNL
13h 02m1 stop
$471Delta
Find Deal
Mon, Oct 27 - Mon, Nov 10
Delta Logo
1:00 pm - 8:53 amHNL-MDW
14h 53m2 stops
Delta Logo
9:20 am - 8:26 pmMDW-HNL
16h 06m2 stops
$476Delta
Find Deal
Mon, Sep 29 - Tue, Oct 28
Delta Logo
4:45 pm - 8:40 amHNL-MDW
10h 55m1 stop
Delta Logo
6:00 am - 3:02 pmMDW-HNL
13h 02m1 stop
$494Delta
Find Deal
Mon, Oct 27 - Tue, Nov 11
Delta Logo
1:15 pm - 10:30 amHNL-MDW
16h 15m2 stops
Delta Logo
6:00 am - 3:02 pmMDW-HNL
13h 02m1 stop
$499Delta
Find Deal
Fri, Oct 24 - Tue, Nov 11
Delta Logo
1:00 pm - 8:53 amHNL-MDW
14h 53m2 stops
Delta Logo
9:20 am - 8:26 pmMDW-HNL
16h 06m2 stops
$505Delta
Find Deal
Tue, Sep 30 - Thu, Oct 30
Southwest Logo
8:05 am - 12:25 amHNL-MDW
11h 20m1 stop
Southwest Logo
2:25 pm - 9:00 pmMDW-HNL
11h 35m1 stop
$508Southwest
Find Deal
Tue, Oct 28 - Fri, Oct 31
Southwest Logo
9:10 pm - 12:35 pmHNL-MDW
10h 25m1 stop
Southwest Logo
9:25 pm - 10:20 amMDW-HNL
17h 55m1 stop
$511Southwest
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Wed, Oct 22 - Mon, Oct 27
Southwest Logo
9:10 pm - 3:10 pmHNL-MDW
13h 00m2 stops
Southwest Logo
7:50 am - 9:00 pmMDW-HNL
17h 10m2 stops
$519Southwest
Find Deal
Mon, Oct 27 - Mon, Nov 10

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
Oct 28
HNL8:05 amHonolulu
11h 20m
1 stop
MDW12:25 amChicago Midway
Oct 31
MDW2:25 pmChicago Midway
11h 35m
1 stop
HNL9:00 pmHonolulu
$508
Find similar
Southwest
Oct 22
HNL9:10 pmHonolulu
10h 25m
1 stop
MDW12:35 pmChicago Midway
Oct 27
MDW9:25 pmChicago Midway
17h 55m
1 stop
HNL10:20 amHonolulu
$511
Find similar
Southwest
Oct 27
HNL9:10 pmHonolulu
13h 00m
2 stops
MDW3:10 pmChicago Midway
Nov 10
MDW7:50 amChicago Midway
17h 10m
2 stops
HNL9:00 pmHonolulu
$519
Find similar

Delta flights from Hawaii to Chicago Midway Airport

Our best Delta deals on Hawaii to Chicago Midway Airport flight tickets
Delta
Oct 27
HNL4:45 pmHonolulu
10h 55m
1 stop
MDW8:40 amChicago Midway
Nov 10
MDW6:00 amChicago Midway
13h 02m
1 stop
HNL3:02 pmHonolulu
$465
Find similar
Delta
Oct 24
HNL1:15 pmHonolulu
16h 15m
2 stops
MDW10:30 amChicago Midway
Nov 10
MDW6:00 amChicago Midway
13h 02m
1 stop
HNL3:02 pmHonolulu
$470
Find similar
Delta
Oct 27
HNL10:31 pmHonolulu
14h 12m
2 stops
MDW5:43 pmChicago Midway
Nov 10
MDW6:00 amChicago Midway
13h 02m
1 stop
HNL3:02 pmHonolulu
$471
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 August 21, 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

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/27

4:45 pm-8:40 am

1 stop10h 55m

Chicago Midway

Mon 11/10

6:00 am-3:02 pm

1 stop13h 02m

$465

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 10/24

1:15 pm-10:30 am

2 stops16h 15m

Chicago Midway

Mon 11/10

6:00 am-3:02 pm

1 stop13h 02m

$470

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/27

10:31 pm-5:43 pm

2 stops14h 12m

Chicago Midway

Mon 11/10

6:00 am-3:02 pm

1 stop13h 02m

$471

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 9/29

1:00 pm-8:53 am

2 stops14h 53m

Chicago Midway

Tue 10/28

9:20 am-8:26 pm

2 stops16h 06m

$476

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/27

4:45 pm-8:40 am

1 stop10h 55m

Chicago Midway

Tue 11/11

6:00 am-3:02 pm

1 stop13h 02m

$494

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 10/24

1:15 pm-10:30 am

2 stops16h 15m

Chicago Midway

Tue 11/11

6:00 am-3:02 pm

1 stop13h 02m

$499

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 9/30

1:00 pm-8:53 am

2 stops14h 53m

Chicago Midway

Thu 10/30

9:20 am-8:26 pm

2 stops16h 06m

$505

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 10/28

8:05 am-12:25 am

1 stop11h 20m

Chicago Midway

Fri 10/31

2:25 pm-9:00 pm

1 stop11h 35m

$508

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 10/22

9:10 pm-12:35 pm

1 stop10h 25m

Chicago Midway

Mon 10/27

9:25 pm-10:20 am

1 stop17h 55m

$511

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/27

9:10 pm-3:10 pm

2 stops13h 00m

Chicago Midway

Mon 11/10

7:50 am-9:00 pm

2 stops17h 10m

$519

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 31% 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

Direct flights

None
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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  • 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
DeltaPriceFrom $421Free CancellationRating
7.9
7,981 reviews
Search Delta flights
SouthwestPriceFrom $606Free CancellationRating
8.0
4,245 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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