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Cheap flights from Honolulu to Chicago from $270

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 6/1. 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
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
10:10 am - 9:15 pm
MDW
-
HNL
16h 05m
1 stop
$554Southwest
Wed, Sep 9 - Sun, Sep 20
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
7:10 am - 9:10 pm
MDW
-
HNL
19h 00m
2 stops
$560Southwest
Wed, Sep 9 - Sun, Sep 20
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
6:10 am - 12:35 pm
MDW
-
HNL
11h 25m
1 stop
$584Southwest
Thu, Sep 10 - Sun, Sep 13
Southwest Logo
8:10 am - 11:45 pm
HNL
-
MDW
10h 35m
1 stop
Southwest Logo
10:20 am - 9:15 pm
MDW
-
HNL
15h 55m
2 stops
$590Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
8:15 am - 5:55 am
HNL
-
MDW
16h 40m
2 stops
Southwest Logo
7:10 am - 9:10 pm
MDW
-
HNL
19h 00m
2 stops
$595Southwest
Wed, Sep 9 - Sun, Sep 20
Southwest Logo
10:20 pm - 3:15 pm
HNL
-
MDW
11h 55m
2 stops
Southwest Logo
7:10 am - 9:10 pm
MDW
-
HNL
19h 00m
2 stops
$610Southwest
Thu, Sep 17 - Sun, Sep 20
Southwest Logo
8:00 am - 4:30 am
HNL
-
MDW
15h 30m
2 stops
Southwest Logo
7:10 am - 9:10 pm
MDW
-
HNL
19h 00m
2 stops
$625Southwest
Thu, Sep 10 - Sun, Sep 13
Southwest Logo
9:25 pm - 5:05 pm
HNL
-
MDW
14h 40m
1 stop
Southwest Logo
10:50 am - 9:15 pm
MDW
-
HNL
15h 25m
1 stop
$630Southwest
Mon, Oct 26 - Thu, Oct 29
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
Southwest Logo
11:45 am - 9:15 pm
MDW
-
HNL
14h 30m
2 stops
$636Southwest
Mon, Oct 26 - Thu, Oct 29
Southwest Logo
9:25 pm - 3:45 pm
HNL
-
MDW
13h 20m
2 stops
Southwest Logo
10:50 am - 9:10 pm
MDW
-
HNL
15h 20m
2 stops
$641Southwest
Mon, Oct 26 - Thu, Oct 29

Southwest flights from Honolulu to Chicago Midway Airport

Our best Southwest deals on Honolulu to Chicago Midway Airport flight tickets
Southwest
Sep 9
HNL8:10 amHonolulu
15h 20m
1 stop
MDW4:30 amChicago Midway
Sep 20
MDW10:10 amChicago Midway
16h 05m
1 stop
HNL9:15 pmHonolulu
$554
Southwest
Sep 9
HNL8:10 amHonolulu
15h 20m
1 stop
MDW4:30 amChicago Midway
Sep 20
MDW7:10 amChicago Midway
19h 00m
2 stops
HNL9:10 pmHonolulu
$560
Southwest
Sep 10
HNL8:10 amHonolulu
15h 20m
1 stop
MDW4:30 amChicago Midway
Sep 13
MDW6:10 amChicago Midway
11h 25m
1 stop
HNL12:35 pmHonolulu
$584

Delta flights from Honolulu to Chicago Midway Airport

Our best Delta deals on Honolulu to Chicago Midway Airport flight tickets
Delta
Oct 6
HNL2:51 pmHonolulu
12h 54m
1 stop
MDW8:45 amChicago Midway
Oct 21
MDW9:30 amChicago Midway
14h 54m
2 stops
HNL7:24 pmHonolulu
$699
Delta
Oct 6
HNL4:05 pmHonolulu
15h 28m
2 stops
MDW12:33 pmChicago Midway
Oct 21
MDW9:30 amChicago Midway
14h 54m
2 stops
HNL7:24 pmHonolulu
$704
Delta
Oct 6
HNL3:10 pmHonolulu
13h 42m
1 stop
MDW9:52 amChicago Midway
Oct 21
MDW6:00 amChicago Midway
12h 15m
1 stop
HNL1:15 pmHonolulu
$727

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 May 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

Cheapest round-trip

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/9

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 9/20

10:10 am-9:15 pm

1 stop16h 05m

$554

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/9

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 9/20

7:10 am-9:10 pm

2 stops19h 00m

$560

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/10

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 9/13

6:10 am-12:35 pm

1 stop11h 25m

$584
Quickest round-trip

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/10

8:10 am-11:45 pm

1 stop10h 35m

Chicago Midway

Mon 9/14

10:20 am-9:15 pm

2 stops15h 55m

$590

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/9

8:15 am-5:55 am

2 stops16h 40m

Chicago Midway

Sun 9/20

7:10 am-9:10 pm

2 stops19h 00m

$595

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/17

10:20 pm-3:15 pm

2 stops11h 55m

Chicago Midway

Sun 9/20

7:10 am-9:10 pm

2 stops19h 00m

$610

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/10

8:00 am-4:30 am

2 stops15h 30m

Chicago Midway

Sun 9/13

7:10 am-9:10 pm

2 stops19h 00m

$625

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/26

9:25 pm-5:05 pm

1 stop14h 40m

Chicago Midway

Thu 10/29

10:50 am-9:15 pm

1 stop15h 25m

$630

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/26

8:15 am-5:00 am

1 stop15h 45m

Chicago Midway

Thu 10/29

11:45 am-9:15 pm

2 stops14h 30m

$636

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/26

9:25 pm-3:45 pm

2 stops13h 20m

Chicago Midway

Thu 10/29

10:50 am-9:10 pm

2 stops15h 20m

$641

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 29% 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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Frequently asked questions about flying from Honolulu to Chicago Midway Airport

  • 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
4,295 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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.

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