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Cheap flights from Hawaii to Chicago 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 Hawaii to Chicago departing on 8/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Hawaii to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:15 pm - 11:35 am
HNL
-
MDW
16h 20m
1 stop
Southwest Logo
10:10 am - 9:20 pm
MDW
-
HNL
15h 10m
1 stop
$434Southwest
Wed, Nov 11 - Sun, Nov 15
Southwest Logo
3:15 pm - 11:35 am
HNL
-
MDW
16h 20m
1 stop
Southwest Logo
7:30 am - 9:10 pm
MDW
-
HNL
17h 40m
2 stops
$440Southwest
Wed, Nov 11 - Sun, Nov 15
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
5:40 am - 1:05 pm
MDW
-
HNL
12h 25m
1 stop
$464Southwest
Wed, Aug 26 - Sun, Aug 30
Southwest Logo
11:55 am - 5:45 am
HNL
-
MDW
12h 50m
1 stop
Southwest Logo
1:40 pm - 9:15 pm
MDW
-
HNL
12h 35m
2 stops
$470Southwest
Thu, Aug 27 - Sun, Aug 30
Southwest Logo
9:00 pm - 3:05 pm
HNL
-
MDW
13h 05m
1 stop
Southwest Logo
6:15 am - 12:35 pm
MDW
-
HNL
11h 20m
1 stop
$494Southwest
Tue, Aug 25 - Mon, Aug 31
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
1:50 pm - 9:15 pm
MDW
-
HNL
12h 25m
2 stops
$500Southwest
Tue, Aug 25 - Mon, Aug 31
Southwest Logo
9:25 pm - 4:35 pm
HNL
-
MDW
14h 10m
1 stop
Southwest Logo
10:15 am - 9:20 pm
MDW
-
HNL
16h 05m
1 stop
$524Southwest
Tue, Sep 1 - Tue, Sep 15
Southwest Logo
9:55 pm - 3:05 pm
HNL
-
MDW
12h 10m
2 stops
Southwest Logo
2:50 pm - 9:20 pm
MDW
-
HNL
11h 30m
1 stop
$530Southwest
Tue, Aug 25 - Mon, Aug 31
Southwest Logo
9:55 pm - 3:05 pm
HNL
-
MDW
12h 10m
2 stops
Southwest Logo
1:50 pm - 9:15 pm
MDW
-
HNL
12h 25m
2 stops
$535Southwest
Tue, Aug 25 - Mon, Aug 31
Delta Logo
8:42 pm - 6:33 pm
KOA
-
MDW
16h 51m
2 stops
Delta Logo
9:59 am - 7:17 pm
MDW
-
KOA
14h 18m
2 stops
$910Delta
Fri, Aug 7 - Tue, Aug 11

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Delta flights from Hawaii to Chicago Midway Airport

Our best Delta deals on Hawaii to Chicago Midway Airport flight tickets
Delta
Sep 8
HNL4:13 pmHonolulu
13h 23m
2 stops
MDW10:36 amChicago Midway
Sep 15
MDW9:29 amChicago Midway
16h 43m
2 stops
HNL9:12 pmHonolulu
$626
Delta
Sep 7
HNL2:50 pmHonolulu
14h 46m
2 stops
MDW10:36 amChicago Midway
Sep 21
MDW9:29 amChicago Midway
16h 43m
2 stops
HNL9:12 pmHonolulu
$673
Delta
Aug 25
HNL2:50 pmHonolulu
13h 27m
1 stop
MDW9:17 amChicago Midway
Aug 31
MDW6:05 amChicago Midway
12h 15m
1 stop
HNL1:20 pmHonolulu
$690

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
Nov 11
HNL3:15 pmHonolulu
16h 20m
1 stop
MDW11:35 amChicago Midway
Nov 15
MDW10:10 amChicago Midway
15h 10m
1 stop
HNL9:20 pmHonolulu
$434
Southwest
Nov 11
HNL3:15 pmHonolulu
16h 20m
1 stop
MDW11:35 amChicago Midway
Nov 15
MDW7:30 amChicago Midway
17h 40m
2 stops
HNL9:10 pmHonolulu
$440
Southwest
Aug 26
HNL8:10 amHonolulu
15h 20m
1 stop
MDW4:30 amChicago Midway
Aug 30
MDW5:40 amChicago Midway
12h 25m
1 stop
HNL1:05 pmHonolulu
$464

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 July 26, 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 11/11

3:15 pm-11:35 am

1 stop16h 20m

Chicago Midway

Sun 11/15

10:10 am-9:20 pm

1 stop15h 10m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 11/11

3:15 pm-11:35 am

1 stop16h 20m

Chicago Midway

Sun 11/15

7:30 am-9:10 pm

2 stops17h 40m

$440

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 8/26

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 8/30

5:40 am-1:05 pm

1 stop12h 25m

$464

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 8/27

11:55 am-5:45 am

1 stop12h 50m

Chicago Midway

Sun 8/30

1:40 pm-9:15 pm

2 stops12h 35m

$470

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 8/25

9:00 pm-3:05 pm

1 stop13h 05m

Chicago Midway

Mon 8/31

6:15 am-12:35 pm

1 stop11h 20m

$494

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 8/25

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Mon 8/31

1:50 pm-9:15 pm

2 stops12h 25m

$500

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 9/1

9:25 pm-4:35 pm

1 stop14h 10m

Chicago Midway

Tue 9/15

10:15 am-9:20 pm

1 stop16h 05m

$524
Quickest round-trip

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 8/25

9:55 pm-3:05 pm

2 stops12h 10m

Chicago Midway

Mon 8/31

2:50 pm-9:20 pm

1 stop11h 30m

$530

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 8/25

9:55 pm-3:05 pm

2 stops12h 10m

Chicago Midway

Mon 8/31

1:50 pm-9:15 pm

2 stops12h 25m

$535

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 8/7

8:42 pm-6:33 pm

2 stops16h 51m

Chicago Midway

Tue 8/11

9:59 am-7:17 pm

2 stops14h 18m

$910

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 10% 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 25m

Direct flights

None
The fastest flight from Hawaii to Chicago Midway Airport takes 10h 25m
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 $580Free CancellationRating
8.0
4,231 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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