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Cheap flights from Honolulu to Chicago from $176

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 5/13. 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 Honolulu to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:00 pm - 11:05 am
HNL
-
MDW
17h 05m
1 stop
Southwest Logo
10:10 am - 9:05 pm
MDW
-
HNL
15h 55m
1 stop
$352Southwest
Thu, Apr 23 - Tue, Apr 28
Southwest Logo
1:00 pm - 11:05 am
HNL
-
MDW
17h 05m
1 stop
Southwest Logo
7:30 am - 9:00 pm
MDW
-
HNL
18h 30m
2 stops
$358Southwest
Thu, Apr 23 - Tue, Apr 28
Southwest Logo
8:05 am - 12:25 am
HNL
-
MDW
12h 20m
1 stop
Southwest Logo
9:30 pm - 10:00 am
MDW
-
HNL
17h 30m
1 stop
$440Southwest
Mon, Mar 2 - Mon, Mar 9
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
$448Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
1:55 pm - 9:06 am
HNL
-
MDW
15h 11m
2 stops
Delta Logo
9:35 am - 8:51 pm
MDW
-
HNL
16h 16m
2 stops
$453Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
12:31 pm - 8:51 am
HNL
-
MDW
15h 20m
2 stops
Delta Logo
9:31 am - 9:45 pm
MDW
-
HNL
17h 14m
2 stops
$475Delta
Thu, Apr 30 - Wed, May 6
Delta Logo
12:31 pm - 8:51 am
HNL
-
MDW
15h 20m
2 stops
Delta Logo
9:31 am - 9:45 pm
MDW
-
HNL
17h 14m
2 stops
$485Delta
Thu, Apr 30 - Wed, May 6
Southwest Logo
9:25 pm - 4:45 pm
HNL
-
MDW
14h 20m
1 stop
Southwest Logo
10:00 am - 4:20 pm
MDW
-
HNL
11h 20m
1 stop
$503Southwest
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
9:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
Southwest Logo
10:30 am - 5:40 pm
MDW
-
HNL
12h 10m
1 stop
$504Southwest
Thu, Mar 5 - Wed, Mar 11
Delta Logo
4:10 pm - 12:43 pm
HNL
-
MDW
15h 33m
2 stops
Delta Logo
9:31 am - 9:45 pm
MDW
-
HNL
17h 14m
2 stops
$505Delta
Thu, Apr 23 - Tue, Apr 28

Delta flights from Honolulu to Chicago Midway Airport

Our best Delta deals on Honolulu 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
$448
Delta
Mar 2
HNL1:55 pmHonolulu
15h 11m
2 stops
MDW9:06 amChicago Midway
Mar 9
MDW9:35 amChicago Midway
16h 16m
2 stops
HNL8:51 pmHonolulu
$453
Delta
Apr 30
HNL12:31 pmHonolulu
15h 20m
2 stops
MDW8:51 amChicago Midway
May 6
MDW9:31 amChicago Midway
17h 14m
2 stops
HNL9:45 pmHonolulu
$475

Southwest flights from Honolulu to Chicago Midway Airport

Our best Southwest deals on Honolulu to Chicago Midway Airport flight tickets
Southwest
Apr 23
HNL1:00 pmHonolulu
17h 05m
1 stop
MDW11:05 amChicago Midway
Apr 28
MDW10:10 amChicago Midway
15h 55m
1 stop
HNL9:05 pmHonolulu
$352
Southwest
Apr 23
HNL1:00 pmHonolulu
17h 05m
1 stop
MDW11:05 amChicago Midway
Apr 28
MDW7:30 amChicago Midway
18h 30m
2 stops
HNL9:00 pmHonolulu
$358
Southwest
Mar 2
HNL8:05 amHonolulu
12h 20m
1 stop
MDW12:25 amChicago Midway
Mar 9
MDW9:30 pmChicago Midway
17h 30m
1 stop
HNL10:00 amHonolulu
$440

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 February 12, 2026.
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

Thu 4/23

1:00 pm-11:05 am

1 stop17h 05m

Chicago Midway

Tue 4/28

10:10 am-9:05 pm

1 stop15h 55m

$352

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/23

1:00 pm-11:05 am

1 stop17h 05m

Chicago Midway

Tue 4/28

7:30 am-9:00 pm

2 stops18h 30m

$358

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

8:05 am-12:25 am

1 stop12h 20m

Chicago Midway

Mon 3/9

9:30 pm-10:00 am

1 stop17h 30m

$440

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

$448

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

1:55 pm-9:06 am

2 stops15h 11m

Chicago Midway

Mon 3/9

9:35 am-8:51 pm

2 stops16h 16m

$453

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/30

12:31 pm-8:51 am

2 stops15h 20m

Chicago Midway

Wed 5/6

9:31 am-9:45 pm

2 stops17h 14m

$475

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/30

12:31 pm-8:51 am

2 stops15h 20m

Chicago Midway

Wed 5/6

9:31 am-9:45 pm

2 stops17h 14m

$485

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 3/10

9:25 pm-4:45 pm

1 stop14h 20m

Chicago Midway

Tue 3/17

10:00 am-4:20 pm

1 stop11h 20m

$503

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 3/5

9:15 am-5:00 am

1 stop15h 45m

Chicago Midway

Wed 3/11

10:30 am-5:40 pm

1 stop12h 10m

$504

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/23

4:10 pm-12:43 pm

2 stops15h 33m

Chicago Midway

Tue 4/28

9:31 am-9:45 pm

2 stops17h 14m

$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

Can stopping save me money on Honolulu to Chicago Midway Airport flights?

You could potentially save up to 2% 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 50m

Direct flights

None
The fastest flight from Honolulu to Chicago Midway Airport takes 11h 50m
There are no direct flights from Honolulu to Chicago Midway Airport. There are no popular flight routes from Honolulu to Chicago Midway Airport.
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  • 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 50m, 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
8.0
4,283 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 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.

An easier way to manage your Chicago Midway Airport trip

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