Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Hawaii to Chicago from $209

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.
Delta Logo
9:46 pm - 6:00 pmLIH  Lihue-MDW Chicago Midway
16h 14m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
9:38 am - 8:21 pmMDW  Chicago Midway-LIH Lihue
14h 43m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$435Delta
Thu, Jan 28 - Sun, Feb 7
Southwest Logo
9:30 pm - 4:25 pmLIH  Lihue-MDW Chicago Midway
14h 55m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:55 am - 8:30 pmMDW  Chicago Midway-LIH Lihue
14h 35m2 stops Oakland Honolulu
$503Southwest
Thu, Jan 28 - Sun, Feb 7
Delta Logo
10:17 pm - 4:39 pmOGG  Kahului-MDW Chicago Midway
14h 22m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
6:00 am - 2:29 pmMDW  Chicago Midway-OGG Kahului
12h 29m1 stop Atlanta Hartsfield-Jackson
$544Delta
Tue, Nov 17 - Tue, Nov 24
Delta Logo
4:25 pm - 9:46 amHNL  Honolulu-MDW Chicago Midway
13h 21m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 2:40 pmMDW  Chicago Midway-HNL Honolulu
12h 40m1 stop Atlanta Hartsfield-Jackson
$557Delta
Thu, Nov 19 - Mon, Nov 23
Delta Logo
1:59 pm - 8:50 amHNL  Honolulu-MDW Chicago Midway
14h 51m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
6:00 am - 2:40 pmMDW  Chicago Midway-HNL Honolulu
12h 40m1 stop Atlanta Hartsfield-Jackson
$563Delta
Wed, Nov 18 - Mon, Nov 23
Delta Logo
4:25 pm - 9:46 amHNL  Honolulu-MDW Chicago Midway
13h 21m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 2:40 pmMDW  Chicago Midway-HNL Honolulu
12h 40m1 stop Atlanta Hartsfield-Jackson
$564Delta
Thu, Nov 12 - Tue, Nov 17
Delta Logo
9:10 pm - 6:37 pmOGG  Kahului-MDW Chicago Midway
16h 27m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 1:52 pmMDW  Chicago Midway-OGG Kahului
12h 52m1 stop Atlanta Hartsfield-Jackson
$564Delta
Tue, Apr 6 - Tue, Apr 13
Southwest Logo
11:10 pm - 4:45 pmOGG  Kahului-MDW Chicago Midway
13h 35m1 stop San Diego
Southwest Logo
10:15 am - 8:25 pmMDW  Chicago Midway-OGG Kahului
14h 10m2 stops Los Angeles Honolulu
$568Southwest
Wed, Jan 13 - Thu, Jan 21
Delta Logo
9:10 pm - 6:37 pmOGG  Kahului-MDW Chicago Midway
16h 27m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
9:55 am - 8:38 pmMDW  Chicago Midway-OGG Kahului
15h 43m2 stops Minneapolis St Paul Los Angeles
$569Delta
Tue, Apr 6 - Tue, Apr 13
Delta Logo
4:25 pm - 9:46 amHNL  Honolulu-MDW Chicago Midway
13h 21m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 9:04 pmMDW  Chicago Midway-HNL Honolulu
15h 34m2 stops Detroit Metropolitan Wayne County Los Angeles
$570Delta
Thu, Nov 12 - Tue, Nov 17

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

Delta flights from Hawaii to Chicago Midway Airport

Our best Delta deals on Hawaii to Chicago Midway Airport flight tickets
Delta
Jan 28
LIH9:46 pmLihue
16h 14m
2 stops
MDW6:00 pmChicago Midway
Feb 7
MDW9:38 amChicago Midway
14h 43m
2 stops
LIH8:21 pmLihue
$435
Delta
Nov 17
OGG10:17 pmKahului
14h 22m
2 stops
MDW4:39 pmChicago Midway
Nov 24
MDW6:00 amChicago Midway
12h 29m
1 stop
OGG2:29 pmKahului
$544
Delta
Nov 19
HNL4:25 pmHonolulu
13h 21m
1 stop
MDW9:46 amChicago Midway
Nov 23
MDW6:00 amChicago Midway
12h 40m
1 stop
HNL2:40 pmHonolulu
$557

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
Jan 28
LIH9:30 pmLihue
14h 55m
1 stop
MDW4:25 pmChicago Midway
Feb 7
MDW9:55 amChicago Midway
14h 35m
2 stops
LIH8:30 pmLihue
$503
Southwest
Jan 13
OGG11:10 pmKahului
13h 35m
1 stop
MDW4:45 pmChicago Midway
Jan 21
MDW10:15 amChicago Midway
14h 10m
2 stops
OGG8:25 pmKahului
$568
Southwest
Apr 16
HNL2:25 pmHonolulu
10h 20m
1 stop
MDW5:45 amChicago Midway
Apr 19
MDW6:50 amChicago Midway
11h 30m
1 stop
HNL1:20 pmHonolulu
$572

momondo Fare Finder

 
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

LihueChicago

LIH Lihue - MDW Chicago Midway

LIHMDW

Lihue

Thu 1/28

9:46 pm-6:00 pm

2 stops16h 14m

Chicago Midway

Sun 2/7

9:38 am-8:21 pm

2 stops14h 43m

$435

LihueChicago

LIH Lihue - MDW Chicago Midway

LIHMDW

Lihue

Thu 1/28

9:30 pm-4:25 pm

1 stop14h 55m

Chicago Midway

Sun 2/7

9:55 am-8:30 pm

2 stops14h 35m

$503

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Tue 11/17

10:17 pm-4:39 pm

2 stops14h 22m

Chicago Midway

Tue 11/24

6:00 am-2:29 pm

1 stop12h 29m

$544
Quickest round-trip

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Thu 11/19

4:25 pm-9:46 am

1 stop13h 21m

Chicago Midway

Mon 11/23

6:00 am-2:40 pm

1 stop12h 40m

$557

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Wed 11/18

1:59 pm-8:50 am

2 stops14h 51m

Chicago Midway

Mon 11/23

6:00 am-2:40 pm

1 stop12h 40m

$563

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Thu 11/12

4:25 pm-9:46 am

1 stop13h 21m

Chicago Midway

Tue 11/17

6:00 am-2:40 pm

1 stop12h 40m

$564

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Tue 4/6

9:10 pm-6:37 pm

2 stops16h 27m

Chicago Midway

Tue 4/13

6:00 am-1:52 pm

1 stop12h 52m

$564

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Wed 1/13

11:10 pm-4:45 pm

1 stop13h 35m

Chicago Midway

Thu 1/21

10:15 am-8:25 pm

2 stops14h 10m

$568

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Tue 4/6

9:10 pm-6:37 pm

2 stops16h 27m

Chicago Midway

Tue 4/13

9:55 am-8:38 pm

2 stops15h 43m

$569

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Thu 11/12

4:25 pm-9:46 am

1 stop13h 21m

Chicago Midway

Tue 11/17

9:30 am-9:04 pm

2 stops15h 34m

$570

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 19% 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

Best Price Found

$209

Fastest flight time

9h 45m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Hawaii in the past 72 hours is $209. The best round-trip flight deal from Hawaii to Chicago Midway Airport found on momondo in the last 72 hours is $435.
The fastest flight from Hawaii to Chicago Midway Airport takes 9h 45m
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

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 $494Free CancellationRating
7.9
4,217 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
Lansing
Saint Joseph
Benton Harbor
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

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
Sun 11/29
Sun 12/6
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago