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Cheap flights from Hawaii to Chicago Midway Airport from $211

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 Midway Airport departing on 1/15. 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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Find the cheapest flights from Hawaii to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Hawaii to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Hawaii to Chicago.

Cheap last minute flights

Planning a quick getaway from Hawaii to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Hawaii to Chicago

Find recent round-trip train or bus tickets from Hawaii to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
6:00 am - 2:56 pmMDW-HNL
12h 56m1 stop
$503Delta
Find Deal
Mon, Jan 13 - Sun, Jan 19
9:40 pm - 6:32 pmLIH-MDW
16h 52m2 stops
9:34 am - 8:09 pmMDW-LIH
14h 35m2 stops
$517Delta
Find Deal
Mon, Dec 16 - Wed, Jan 8
9:00 pm - 5:01 pmKOA-MDW
16h 01m2 stops
9:30 am - 7:49 pmMDW-KOA
14h 19m2 stops
$562Delta
Find Deal
Thu, Dec 5 - Mon, Dec 9
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
9:34 am - 9:55 pmMDW-HNL
16h 21m2 stops
$567Delta
Find Deal
Sun, Jan 12 - Sun, Jan 19
6:40 pm - 1:08 pmHNL-MDW
14h 28m2 stops
9:34 am - 9:55 pmMDW-HNL
16h 21m2 stops
$572Delta
Find Deal
Sun, Jan 12 - Sun, Jan 19
8:10 am - 11:35 pmHNL-MDW
10h 25m1 stop
12:45 pm - 9:00 pmMDW-HNL
13h 15m1 stop
$614Southwest
Find Deal
Tue, Apr 1 - Tue, Apr 8
8:40 am - 5:20 amHNL-MDW
15h 40m2 stops
10:40 pm - 11:50 amMDW-HNL
18h 10m1 stop
$619Southwest
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Tue, Apr 1 - Mon, Apr 7
8:10 am - 5:20 amHNL-MDW
16h 10m2 stops
12:35 pm - 9:00 pmMDW-HNL
13h 25m2 stops
$624Southwest
Find Deal
Tue, Apr 1 - Tue, Apr 8
8:10 am - 11:00 pmHNL-MDW
10h 50m1 stop
9:40 am - 6:40 pmMDW-HNL
13h 00m1 stop
$628Southwest
Find Deal
Sun, Jan 12 - Sun, Jan 19
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
6:00 am - 2:56 pmMDW-HNL
12h 56m1 stop
$632Delta
Find Deal
Sun, Jan 12 - Sun, Jan 19
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
$211Delta
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Wed, Jan 15
6:40 pm - 1:08 pmHNL-MDW
14h 28m2 stops
$216Delta
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Wed, Jan 15
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
$222Delta
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Mon, Jan 20
4:45 pm - 9:23 amOGG-MDW
12h 38m1 stop
$237Delta
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Mon, Dec 23
8:10 am - 11:30 pmHNL-MDW
11h 20m1 stop
$272Southwest
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Thu, Feb 27
12:10 pm - 5:15 amHNL-MDW
12h 05m1 stop
$274Southwest
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Fri, May 2
10:30 am - 9:05 amHNL-MDW
18h 35m2 stops
$283Southwest
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Fri, Feb 28
3:40 pm - 6:32 pmHNL-MDW
22h 52m3 stops
$758WestJet
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Wed, Dec 4
11:45 pm - 12:46 pmHNL-MDW
33h 01m3 stops
$776WestJet
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Tue, Jan 21
11:55 pm - 12:46 pmHNL-MDW
32h 51m3 stops
$787WestJet
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Sat, Jan 18
5:00 pm - 9:32 amHNL-MDW
12h 32m1 stop
6:00 am - 3:14 pmMDW-HNL
13h 14m1 stop
$571Delta
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Fri, Nov 22 - Tue, Nov 26
6:35 pm - 12:49 pmHNL-MDW
14h 14m2 stops
6:00 am - 3:14 pmMDW-HNL
13h 14m1 stop
$576Delta
Find Deal
Fri, Nov 22 - Tue, Nov 26
6:35 pm - 12:49 pmHNL-MDW
14h 14m2 stops
9:31 am - 8:19 pmMDW-HNL
14h 48m2 stops
$581Delta
Find Deal
Fri, Nov 22 - Tue, Nov 26
4:55 pm - 8:50 amHNL-MDW
11h 55m1 stop
6:00 am - 3:14 pmMDW-HNL
13h 14m1 stop
$710Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
11:30 pm - 6:32 pmHNL-MDW
15h 02m2 stops
6:00 am - 3:14 pmMDW-HNL
13h 14m1 stop
$715Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
6:35 pm - 12:49 pmHNL-MDW
14h 14m2 stops
9:31 am - 8:19 pmMDW-HNL
14h 48m2 stops
$720Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
8:15 am - 11:45 pmLIH-MDW
11h 30m1 stop
6:05 am - 3:20 pmMDW-LIH
13h 15m1 stop
$772Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
8:15 am - 1:40 amLIH-MDW
13h 25m2 stops
6:05 am - 3:20 pmMDW-LIH
13h 15m1 stop
$777Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
4:55 pm - 8:50 amHNL-MDW
11h 55m1 stop
6:00 am - 3:14 pmMDW-HNL
13h 14m1 stop
$869Delta
Find Deal
Fri, Nov 22 - Sun, Nov 24
8:15 am - 1:40 amLIH-MDW
13h 25m2 stops
5:35 am - 7:50 pmMDW-LIH
18h 15m2 stops
$912Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3

Delta flights from Hawaii to Chicago Midway Airport

Our best Delta deals on Hawaii to Chicago Midway Airport flight tickets
Delta
Jan 13
HNL4:50 pmHonolulu
12h 04m
1 stop
MDW8:54 amChicago Midway
Jan 19
MDW6:00 amChicago Midway
12h 56m
1 stop
HNL2:56 pmHonolulu
Delta
Dec 16
LIH9:40 pmLihue
16h 52m
2 stops
MDW6:32 pmChicago Midway
Jan 8
MDW9:34 amChicago Midway
14h 35m
2 stops
LIH8:09 pmLihue
Delta
Dec 5
KOA9:00 pmKona Intl
16h 01m
2 stops
MDW5:01 pmChicago Midway
Dec 9
MDW9:30 amChicago Midway
14h 19m
2 stops
KOA7:49 pmKona Intl

Southwest flights from Hawaii to Chicago Midway Airport

Our best Southwest deals on Hawaii to Chicago Midway Airport flight tickets
Southwest
Apr 1
HNL8:10 amHonolulu
10h 25m
1 stop
MDW11:35 pmChicago Midway
Apr 8
MDW12:45 pmChicago Midway
13h 15m
1 stop
HNL9:00 pmHonolulu
Southwest
Apr 1
HNL8:40 amHonolulu
15h 40m
2 stops
MDW5:20 amChicago Midway
Apr 7
MDW10:40 pmChicago Midway
18h 10m
1 stop
HNL11:50 amHonolulu
Southwest
Apr 1
HNL8:10 amHonolulu
16h 10m
2 stops
MDW5:20 amChicago Midway
Apr 8
MDW12:35 pmChicago Midway
13h 25m
2 stops
HNL9:00 pmHonolulu

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, Monday is the cheapest day to fly to Chicago Midway Airport from Hawaii. The lowest ticket price found for a Monday departure recently was $0. 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 in the morning is the least expensive time of day to depart. momondo users have found prices as low as $0 when looking at flights departing in the morning. 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 2% 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

$211

Fastest flight time

10h 00m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Hawaii in the past 72 hours is $211. The best round-trip flight deal from Hawaii to Chicago Midway Airport found on momondo in the last 72 hours is $503.
The fastest flight from Hawaii to Chicago Midway Airport takes 10h 00m
There are no direct flights from Hawaii to Chicago Midway Airport. Popular non-direct routes for this connection are Honolulu Airport - Chicago Midway Airport, Kahului Airport - Chicago Midway Airport and Kona Intl Airport - 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
DeltaPriceFrom $421Free CancellationRating
8.0
8,755 reviews
Search Delta flights

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.


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