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Cheap flights from Hawaii to Chicago from $252

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
1:05 pm - 8:44 amHNL  Honolulu-MDW Chicago Midway
14h 39m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
9:29 am - 8:48 pmMDW  Chicago Midway-HNL Honolulu
15h 19m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$497Delta
Fri, Oct 30 - Thu, Nov 5
Delta Logo
1:05 pm - 9:32 amHNL  Honolulu-MDW Chicago Midway
15h 27m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
6:04 am - 7:48 pmMDW  Chicago Midway-HNL Honolulu
18h 44m2 stops Atlanta Hartsfield-Jackson Seattle/Tacoma Intl
$497Delta
Tue, Oct 6 - Wed, Oct 21
Delta Logo
1:05 pm - 10:32 amHNL  Honolulu-MDW Chicago Midway
16h 27m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 8:48 pmMDW  Chicago Midway-HNL Honolulu
15h 19m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$497Delta
Sat, Oct 31 - Fri, Nov 6
Delta Logo
1:05 pm - 9:32 amHNL  Honolulu-MDW Chicago Midway
15h 27m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 8:48 pmMDW  Chicago Midway-HNL Honolulu
15h 19m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$497Delta
Thu, Oct 29 - Thu, Nov 5
Delta Logo
2:51 pm - 9:32 amHNL  Honolulu-MDW Chicago Midway
13h 41m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:04 am - 7:48 pmMDW  Chicago Midway-HNL Honolulu
18h 44m2 stops Atlanta Hartsfield-Jackson Seattle/Tacoma Intl
$511Delta
Wed, Oct 14 - Tue, Oct 20
Delta Logo
4:15 pm - 9:32 amHNL  Honolulu-MDW Chicago Midway
13h 17m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 8:38 pmMDW  Chicago Midway-HNL Honolulu
15h 08m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$511Delta
Thu, Nov 5 - Sat, Nov 14
Southwest Logo
12:05 pm - 5:40 amHNL  Honolulu-MDW Chicago Midway
12h 35m1 stop Ontario
Southwest Logo
6:25 am - 12:40 pmMDW  Chicago Midway-HNL Honolulu
11h 15m1 stop San Diego
$524Southwest
Fri, Oct 23 - Tue, Oct 27
Southwest Logo
8:10 am - 4:25 amHNL  Honolulu-MDW Chicago Midway
16h 15m1 stop San Diego
Southwest Logo
10:15 am - 9:05 pmMDW  Chicago Midway-HNL Honolulu
14h 50m1 stop Sacramento Intl
$524Southwest
Thu, Nov 5 - Sun, Nov 8
Southwest Logo
3:15 pm - 11:35 amHNL  Honolulu-MDW Chicago Midway
16h 20m1 stop Oakland
Southwest Logo
7:25 am - 9:05 pmMDW  Chicago Midway-HNL Honolulu
17h 40m2 stops Los Angeles Los Angeles Sacramento Intl
$530Southwest
Thu, Nov 5 - Sun, Nov 8
Southwest Logo
9:30 pm - 2:10 pmKOA  Kona Intl-MDW Chicago Midway
12h 40m1 stop Las Vegas Harry Reid Intl
Southwest Logo
7:25 am - 9:25 pmMDW  Chicago Midway-KOA Kona Intl
18h 00m2 stops Los Angeles Los Angeles Honolulu
$530Southwest
Tue, Nov 3 - Mon, Nov 9

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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
Oct 6
HNL1:05 pmHonolulu
15h 27m
2 stops
MDW9:32 amChicago Midway
Oct 21
MDW6:04 amChicago Midway
18h 44m
2 stops
HNL7:48 pmHonolulu
$497
Delta
Oct 6
HNL2:51 pmHonolulu
13h 41m
1 stop
MDW9:32 amChicago Midway
Oct 21
MDW9:29 amChicago Midway
15h 19m
2 stops
HNL7:48 pmHonolulu
$511
Delta
Oct 14
HNL4:10 pmHonolulu
15h 37m
2 stops
MDW12:47 pmChicago Midway
Oct 20
MDW6:04 amChicago Midway
18h 44m
2 stops
HNL7:48 pmHonolulu
$516

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
Nov 3
KOA9:30 pmKona Intl
12h 40m
1 stop
MDW2:10 pmChicago Midway
Nov 9
MDW7:25 amChicago Midway
18h 00m
2 stops
KOA9:25 pmKona Intl
$530
Southwest
Nov 3
KOA11:40 amKona Intl
14h 15m
2 stops
MDW5:55 amChicago Midway
Nov 9
MDW7:25 amChicago Midway
18h 00m
2 stops
KOA9:25 pmKona Intl
$535
Southwest
Oct 23
OGG10:00 amKahului
14h 55m
1 stop
MDW5:55 amChicago Midway
Oct 28
MDW10:00 amChicago Midway
11h 10m
1 stop
OGG4:10 pmKahului
$539

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

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Route

Depart

Return

Price

Cheapest round-trip

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Fri 10/30

1:05 pm-8:44 am

2 stops14h 39m

Chicago Midway

Thu 11/5

9:29 am-8:48 pm

2 stops15h 19m

$497

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Tue 10/6

1:05 pm-9:32 am

2 stops15h 27m

Chicago Midway

Wed 10/21

6:04 am-7:48 pm

2 stops18h 44m

$497

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Sat 10/31

1:05 pm-10:32 am

2 stops16h 27m

Chicago Midway

Fri 11/6

9:29 am-8:48 pm

2 stops15h 19m

$497

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Thu 10/29

1:05 pm-9:32 am

2 stops15h 27m

Chicago Midway

Thu 11/5

9:29 am-8:48 pm

2 stops15h 19m

$497

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Wed 10/14

2:51 pm-9:32 am

1 stop13h 41m

Chicago Midway

Tue 10/20

6:04 am-7:48 pm

2 stops18h 44m

$511

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Thu 11/5

4:15 pm-9:32 am

1 stop13h 17m

Chicago Midway

Sat 11/14

9:30 am-8:38 pm

2 stops15h 08m

$511
Quickest round-trip

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Fri 10/23

12:05 pm-5:40 am

1 stop12h 35m

Chicago Midway

Tue 10/27

6:25 am-12:40 pm

1 stop11h 15m

$524

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Thu 11/5

8:10 am-4:25 am

1 stop16h 15m

Chicago Midway

Sun 11/8

10:15 am-9:05 pm

1 stop14h 50m

$524

HonoluluChicago

HNL Honolulu - MDW Chicago Midway

HNLMDW

Honolulu

Thu 11/5

3:15 pm-11:35 am

1 stop16h 20m

Chicago Midway

Sun 11/8

7:25 am-9:05 pm

2 stops17h 40m

$530

Kailua-KonaChicago

KOA Kona Intl - MDW Chicago Midway

KOAMDW

Kona Intl

Tue 11/3

9:30 pm-2:10 pm

1 stop12h 40m

Chicago Midway

Mon 11/9

7:25 am-9:25 pm

2 stops18h 00m

$530

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 21% 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

$252

Fastest flight time

10h 40m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Hawaii in the past 72 hours is $252. The best round-trip flight deal from Hawaii to Chicago Midway Airport found on momondo in the last 72 hours is $497.
The fastest flight from Hawaii to Chicago Midway Airport takes 10h 40m
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
4,195 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
Porter
Crown Point
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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