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Cheap flights from Hawaii to Chicago from $232

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 12/5. 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
4:44 pm - 8:54 amHNL-MDW
12h 10m1 stop
Delta Logo
6:00 am - 3:11 pmMDW-HNL
13h 11m1 stop
$547Delta
Find Deal
dom., ene. 18 - dom., feb. 1
Southwest Logo
9:25 pm - 3:00 pmOGG-MDW
13h 35m1 stop
Southwest Logo
7:45 am - 6:10 pmMDW-OGG
14h 25m2 stops
$551Southwest
Find Deal
mié., dic. 3 - dom., dic. 7
Delta Logo
5:15 pm - 12:48 pmHNL-MDW
15h 33m2 stops
Delta Logo
6:00 am - 3:11 pmMDW-HNL
13h 11m1 stop
$552Delta
Find Deal
dom., ene. 18 - dom., feb. 1
Delta Logo
9:35 pm - 5:37 pmHNL-MDW
16h 02m2 stops
Delta Logo
6:00 am - 3:11 pmMDW-HNL
13h 11m1 stop
$553Delta
Find Deal
dom., mar. 1 - mar., mar. 3
Southwest Logo
9:35 pm - 3:00 pmOGG-MDW
13h 25m2 stops
Southwest Logo
7:45 am - 6:10 pmMDW-OGG
14h 25m2 stops
$557Southwest
Find Deal
mié., dic. 3 - dom., dic. 7
Southwest Logo
9:25 pm - 3:00 pmOGG-MDW
13h 35m1 stop
Southwest Logo
7:45 am - 4:10 pmMDW-OGG
12h 25m1 stop
$574Southwest
Find Deal
mié., dic. 3 - dom., dic. 7
Delta Logo
9:35 pm - 5:34 pmHNL-MDW
15h 59m2 stops
Delta Logo
9:34 am - 9:28 pmMDW-HNL
15h 54m2 stops
$624Delta
Find Deal
mié., ene. 7 - lun., ene. 12
Southwest Logo
8:00 am - 11:55 pmHNL-MDW
10h 55m1 stop
Southwest Logo
5:25 am - 12:15 pmMDW-HNL
11h 50m1 stop
$653Southwest
Find Deal
jue., abr. 9 - lun., abr. 13
Delta Logo
5:15 pm - 9:08 amHNL-MDW
11h 53m1 stop
Delta Logo
6:00 am - 3:11 pmMDW-HNL
13h 11m1 stop
$655Delta
Find Deal
dom., mar. 1 - mar., mar. 3
Multiple Airlines Logo
3:50 pm - 1:01 pmHNL-MDW
17h 11m1 stop
Multiple Airlines Logo
12:18 pm - 10:48 amMDW-HNL
26h 30m2 stops
$897Multiple Airlines
Find Deal
lun., dic. 1 - lun., dic. 8

Delta flights from Hawaii to Chicago Midway Airport

Our best Delta deals on Hawaii to Chicago Midway Airport flight tickets
Delta
Jan 18
HNL4:44 pmHonolulu
12h 10m
1 stop
MDW8:54 amChicago Midway
Feb 1
MDW6:00 amChicago Midway
13h 11m
1 stop
HNL3:11 pmHonolulu
$547
Find similar
Delta
Jan 18
HNL5:15 pmHonolulu
15h 33m
2 stops
MDW12:48 pmChicago Midway
Feb 1
MDW6:00 amChicago Midway
13h 11m
1 stop
HNL3:11 pmHonolulu
$552
Find similar
Delta
Mar 1
HNL9:35 pmHonolulu
16h 02m
2 stops
MDW5:37 pmChicago Midway
Mar 3
MDW6:00 amChicago Midway
13h 11m
1 stop
HNL3:11 pmHonolulu
$553
Find similar

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
Dec 3
OGG9:25 pmKahului
13h 35m
1 stop
MDW3:00 pmChicago Midway
Dec 7
MDW7:45 amChicago Midway
14h 25m
2 stops
OGG6:10 pmKahului
$551
Find similar
Southwest
Dec 3
OGG9:35 pmKahului
13h 25m
2 stops
MDW3:00 pmChicago Midway
Dec 7
MDW7:45 amChicago Midway
14h 25m
2 stops
OGG6:10 pmKahului
$557
Find similar
Southwest
Dec 3
OGG9:25 pmKahului
13h 35m
1 stop
MDW3:00 pmChicago Midway
Dec 7
MDW7:45 amChicago Midway
12h 25m
1 stop
OGG4:10 pmKahului
$574
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 noviembre 3, 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

dom. 1/18

4:44 pm-8:54 am

1 stop12h 10m

Chicago Midway

dom. 2/1

6:00 am-3:11 pm

1 stop13h 11m

$547

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

mié. 12/3

9:25 pm-3:00 pm

1 stop13h 35m

Chicago Midway

dom. 12/7

7:45 am-6:10 pm

2 stops14h 25m

$551

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

dom. 1/18

5:15 pm-12:48 pm

2 stops15h 33m

Chicago Midway

dom. 2/1

6:00 am-3:11 pm

1 stop13h 11m

$552

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

dom. 3/1

9:35 pm-5:37 pm

2 stops16h 02m

Chicago Midway

mar. 3/3

6:00 am-3:11 pm

1 stop13h 11m

$553

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

mié. 12/3

9:35 pm-3:00 pm

2 stops13h 25m

Chicago Midway

dom. 12/7

7:45 am-6:10 pm

2 stops14h 25m

$557

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

mié. 12/3

9:25 pm-3:00 pm

1 stop13h 35m

Chicago Midway

dom. 12/7

7:45 am-4:10 pm

1 stop12h 25m

$574

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

mié. 1/7

9:35 pm-5:34 pm

2 stops15h 59m

Chicago Midway

lun. 1/12

9:34 am-9:28 pm

2 stops15h 54m

$624

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

jue. 4/9

8:00 am-11:55 pm

1 stop10h 55m

Chicago Midway

lun. 4/13

5:25 am-12:15 pm

1 stop11h 50m

$653

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

dom. 3/1

5:15 pm-9:08 am

1 stop11h 53m

Chicago Midway

mar. 3/3

6:00 am-3:11 pm

1 stop13h 11m

$655

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

lun. 12/1

3:50 pm-1:01 pm

1 stop17h 11m

Chicago Midway

lun. 12/8

12:18 pm-10:48 am

2 stops26h 30m

$897

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

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.
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 $516Free CancellationRating
8.0
4,238 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
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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mié. 12/3
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