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Cheap flights from Honolulu to Chicago from $277

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Honolulu to Chicago departing on 2/16. 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

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Find the cheapest flights from Honolulu to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:50 pm - 9:53 am
HNL
-
MDW
13h 03m1 stop
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m1 stop
$423Delta
Wed, Jan 28 - Tue, Feb 3
Delta Logo
5:15 pm - 12:46 pm
HNL
-
MDW
15h 31m2 stops
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m1 stop
$429Delta
Wed, Jan 28 - Tue, Feb 3
Delta Logo
1:55 pm - 9:08 am
HNL
-
MDW
15h 13m2 stops
Delta Logo
9:32 am - 9:28 pm
MDW
-
HNL
15h 56m2 stops
$434Delta
Wed, Jan 28 - Wed, Feb 4
Southwest Logo
9:55 pm - 12:35 pm
HNL
-
MDW
10h 40m1 stop
Southwest Logo
8:25 am - 4:30 pm
MDW
-
HNL
12h 05m1 stop
$450Southwest
Wed, Jan 28 - Tue, Feb 3
Southwest Logo
12:30 pm - 5:05 am
HNL
-
MDW
12h 35m2 stops
Southwest Logo
8:25 am - 4:30 pm
MDW
-
HNL
12h 05m1 stop
$455Southwest
Wed, Jan 28 - Tue, Feb 3
Southwest Logo
9:55 pm - 12:35 pm
HNL
-
MDW
10h 40m1 stop
Southwest Logo
8:55 pm - 11:15 am
MDW
-
HNL
18h 20m1 stop
$477Southwest
Wed, Jan 28 - Wed, Feb 4
Delta Logo
5:15 pm - 9:08 am
HNL
-
MDW
11h 53m1 stop
Delta Logo
9:32 am - 9:28 pm
MDW
-
HNL
15h 56m2 stops
$493Delta
Wed, Jan 14 - Thu, Jan 22
Delta Logo
5:15 pm - 12:48 pm
HNL
-
MDW
15h 33m2 stops
Delta Logo
9:32 am - 9:28 pm
MDW
-
HNL
15h 56m2 stops
$498Delta
Wed, Jan 14 - Thu, Jan 22
Southwest Logo
9:55 pm - 12:35 pm
HNL
-
MDW
10h 40m1 stop
Southwest Logo
8:55 pm - 11:15 am
MDW
-
HNL
18h 20m1 stop
$499Southwest
Wed, Jan 28 - Wed, Feb 4
Southwest Logo
12:30 pm - 5:05 am
HNL
-
MDW
12h 35m2 stops
Southwest Logo
8:55 pm - 11:15 am
MDW
-
HNL
18h 20m1 stop
$505Southwest
Wed, Jan 28 - Wed, Feb 4

Delta flights from Honolulu to Chicago Midway Airport

Our best Delta deals on Honolulu to Chicago Midway Airport flight tickets
Delta
Jan 28
HNL4:50 pmHonolulu
13h 03m
1 stop
MDW9:53 amChicago Midway
Feb 3
MDW6:00 amChicago Midway
13h 10m
1 stop
HNL3:10 pmHonolulu
$423
Find similar
Delta
Jan 28
HNL5:15 pmHonolulu
15h 31m
2 stops
MDW12:46 pmChicago Midway
Feb 3
MDW6:00 amChicago Midway
13h 10m
1 stop
HNL3:10 pmHonolulu
$429
Find similar
Delta
Jan 28
HNL1:55 pmHonolulu
14h 57m
2 stops
MDW8:52 amChicago Midway
Feb 3
MDW9:33 amChicago Midway
15h 55m
2 stops
HNL9:28 pmHonolulu
$434
Find similar

Southwest flights from Honolulu to Chicago Midway Airport

Our best Southwest deals on Honolulu to Chicago Midway Airport flight tickets
Southwest
Jan 28
HNL9:55 pmHonolulu
10h 40m
1 stop
MDW12:35 pmChicago Midway
Feb 3
MDW8:25 amChicago Midway
12h 05m
1 stop
HNL4:30 pmHonolulu
$450
Find similar
Southwest
Jan 28
HNL12:30 pmHonolulu
12h 35m
2 stops
MDW5:05 amChicago Midway
Feb 3
MDW8:25 amChicago Midway
12h 05m
1 stop
HNL4:30 pmHonolulu
$455
Find similar
Southwest
Jan 28
HNL9:55 pmHonolulu
10h 40m
1 stop
MDW12:35 pmChicago Midway
Feb 4
MDW8:55 pmChicago Midway
18h 20m
1 stop
HNL11:15 amHonolulu
$477
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Honolulu 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 December 16, 2025.
Use the filters below to find and compare flights from Honolulu to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

4:50 pm-9:53 am

1 stop13h 03m

Chicago Midway

Tue 2/3

6:00 am-3:10 pm

1 stop13h 10m

$423

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

5:15 pm-12:46 pm

2 stops15h 31m

Chicago Midway

Tue 2/3

6:00 am-3:10 pm

1 stop13h 10m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

1:55 pm-9:08 am

2 stops15h 13m

Chicago Midway

Wed 2/4

9:32 am-9:28 pm

2 stops15h 56m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

9:55 pm-12:35 pm

1 stop10h 40m

Chicago Midway

Tue 2/3

8:25 am-4:30 pm

1 stop12h 05m

$450

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

12:30 pm-5:05 am

2 stops12h 35m

Chicago Midway

Tue 2/3

8:25 am-4:30 pm

1 stop12h 05m

$455

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

9:55 pm-12:35 pm

1 stop10h 40m

Chicago Midway

Wed 2/4

8:55 pm-11:15 am

1 stop18h 20m

$477

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/14

5:15 pm-9:08 am

1 stop11h 53m

Chicago Midway

Thu 1/22

9:32 am-9:28 pm

2 stops15h 56m

$493

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/14

5:15 pm-12:48 pm

2 stops15h 33m

Chicago Midway

Thu 1/22

9:32 am-9:28 pm

2 stops15h 56m

$498

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

9:55 pm-12:35 pm

1 stop10h 40m

Chicago Midway

Wed 2/4

8:55 pm-11:15 am

1 stop18h 20m

$499

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

12:30 pm-5:05 am

2 stops12h 35m

Chicago Midway

Wed 2/4

8:55 pm-11:15 am

1 stop18h 20m

$505

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 Honolulu 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 Honolulu. 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 Honolulu 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 Honolulu 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 Honolulu to Chicago Midway Airport flights?

You could potentially save up to 32% on your flight if you consider stops on a Honolulu to Chicago Midway Airport flight.

When to book flights from Honolulu to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Honolulu to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Honolulu to Chicago Midway Airport (HNL to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Honolulu to Chicago Midway Airport

Fastest flight time

11h 53m

Direct flights

None
The fastest flight from Honolulu to Chicago Midway Airport takes 11h 53m
There are no direct flights from Honolulu to Chicago Midway Airport. There are no popular flight routes from Honolulu to Chicago Midway Airport.
Search flight deals

  • How far is Honolulu to Chicago Midway by plane?

    A flight from Honolulu to Chicago Midway will travel around 4240.6 mi. Flights usually cover this in 11h 53m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Honolulu Airport to Chicago Midway Airport?

    Prices for flights from Honolulu Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Honolulu Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Honolulu Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Honolulu Airport 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.

  • What is the most popular airline from Honolulu to Chicago Midway Airport?

Best airlines flying from Honolulu to Chicago Midway Airport

Compare and see reviews for airlines that fly from Honolulu to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $581Free CancellationRating
7.9
4,250 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
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Honolulu to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Honolulu to Chicago for you.

Can I find flights from Honolulu to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Honolulu on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Honolulu to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Honolulu.

I’m not ready to book a flight from Honolulu to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Honolulu are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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