Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Hawaii to Chicago from $171

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 2/27. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Hawaii to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:00 pm - 5:50 am
HNL
-
MDW
11h 50m
1 stop
Southwest Logo
10:20 am - 5:40 pm
MDW
-
HNL
12h 20m
1 stop
$342Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
8:05 am - 12:25 am
HNL
-
MDW
12h 20m
1 stop
Southwest Logo
8:50 am - 9:10 pm
MDW
-
HNL
17h 20m
1 stop
$391Southwest
Mon, Mar 2 - Mon, Mar 9
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
Southwest Logo
11:45 am - 9:05 pm
MDW
-
HNL
14h 20m
2 stops
$437Southwest
Wed, Apr 29 - Wed, May 6
Delta Logo
4:45 pm - 8:54 am
HNL
-
MDW
12h 09m
1 stop
Delta Logo
9:30 am - 8:51 pm
MDW
-
HNL
16h 21m
2 stops
$438Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
5:15 pm - 12:46 pm
HNL
-
MDW
15h 31m
2 stops
Delta Logo
9:30 am - 8:51 pm
MDW
-
HNL
16h 21m
2 stops
$443Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
4:10 pm - 12:43 pm
HNL
-
MDW
15h 33m
2 stops
Delta Logo
1:23 pm - 9:45 pm
MDW
-
HNL
13h 22m
2 stops
$465Delta
Thu, Apr 30 - Wed, May 6
Delta Logo
9:35 pm - 5:37 pm
HNL
-
MDW
16h 02m
2 stops
Delta Logo
6:00 am - 2:16 pm
MDW
-
HNL
13h 16m
1 stop
$468Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
10:40 pm - 6:40 pm
LIH
-
MDW
16h 00m
2 stops
Delta Logo
9:35 am - 6:50 pm
MDW
-
LIH
14h 15m
2 stops
$477Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
4:10 pm - 12:43 pm
HNL
-
MDW
15h 33m
2 stops
Delta Logo
1:23 pm - 9:45 pm
MDW
-
HNL
13h 22m
2 stops
$492Delta
Thu, Apr 30 - Wed, May 6
Delta Logo
4:45 pm - 1:05 pm
HNL
-
MDW
16h 20m
2 stops
Delta Logo
9:35 am - 8:51 pm
MDW
-
HNL
16h 16m
2 stops
$500Delta
Mon, Mar 2 - Mon, Mar 9

Delta flights from Hawaii to Chicago Midway Airport

Our best Delta deals on Hawaii to Chicago Midway Airport flight tickets
Delta
Mar 2
HNL4:45 pmHonolulu
12h 09m
1 stop
MDW8:54 amChicago Midway
Mar 9
MDW9:30 amChicago Midway
16h 21m
2 stops
HNL8:51 pmHonolulu
$438
Delta
Mar 2
HNL5:15 pmHonolulu
15h 31m
2 stops
MDW12:46 pmChicago Midway
Mar 9
MDW9:30 amChicago Midway
16h 21m
2 stops
HNL8:51 pmHonolulu
$443
Delta
Apr 30
HNL4:10 pmHonolulu
15h 33m
2 stops
MDW12:43 pmChicago Midway
May 6
MDW1:23 pmChicago Midway
13h 22m
2 stops
HNL9:45 pmHonolulu
$465

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
Apr 29
HNL1:00 pmHonolulu
11h 50m
1 stop
MDW5:50 amChicago Midway
May 6
MDW10:20 amChicago Midway
12h 20m
1 stop
HNL5:40 pmHonolulu
$342
Southwest
Mar 2
HNL8:05 amHonolulu
12h 20m
1 stop
MDW12:25 amChicago Midway
Mar 9
MDW8:50 amChicago Midway
17h 20m
1 stop
HNL9:10 pmHonolulu
$391
Southwest
Apr 29
HNL8:15 amHonolulu
15h 45m
1 stop
MDW5:00 amChicago Midway
May 6
MDW11:45 amChicago Midway
14h 20m
2 stops
HNL9:05 pmHonolulu
$437

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 February 5, 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

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/29

1:00 pm-5:50 am

1 stop11h 50m

Chicago Midway

Wed 5/6

10:20 am-5:40 pm

1 stop12h 20m

$342

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

8:05 am-12:25 am

1 stop12h 20m

Chicago Midway

Mon 3/9

8:50 am-9:10 pm

1 stop17h 20m

$391

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/29

8:15 am-5:00 am

1 stop15h 45m

Chicago Midway

Wed 5/6

11:45 am-9:05 pm

2 stops14h 20m

$437

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

4:45 pm-8:54 am

1 stop12h 09m

Chicago Midway

Mon 3/9

9:30 am-8:51 pm

2 stops16h 21m

$438

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

5:15 pm-12:46 pm

2 stops15h 31m

Chicago Midway

Mon 3/9

9:30 am-8:51 pm

2 stops16h 21m

$443

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/30

4:10 pm-12:43 pm

2 stops15h 33m

Chicago Midway

Wed 5/6

1:23 pm-9:45 pm

2 stops13h 22m

$465

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

9:35 pm-5:37 pm

2 stops16h 02m

Chicago Midway

Mon 3/9

6:00 am-2:16 pm

1 stop13h 16m

$468

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 3/3

10:40 pm-6:40 pm

2 stops16h 00m

Chicago Midway

Tue 3/10

9:35 am-6:50 pm

2 stops14h 15m

$477

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/30

4:10 pm-12:43 pm

2 stops15h 33m

Chicago Midway

Wed 5/6

1:23 pm-9:45 pm

2 stops13h 22m

$492

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

4:45 pm-1:05 pm

2 stops16h 20m

Chicago Midway

Mon 3/9

9:35 am-8:51 pm

2 stops16h 16m

$500

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 50m

Direct flights

None
The fastest flight from Hawaii to Chicago Midway Airport takes 11h 50m
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
4,275 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
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

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 3/7
Sat 3/14
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago