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Cheap flights from Honolulu to Chicago from $247

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 4/22. 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.
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
Delta Logo
6:00 am - 1:45 pm
MDW
-
HNL
12h 45m
1 stop
$494Delta
Tue, Apr 21 - Sun, Apr 26
Delta Logo
12:25 pm - 8:47 am
HNL
-
MDW
15h 22m
2 stops
Delta Logo
6:00 am - 1:45 pm
MDW
-
HNL
12h 45m
1 stop
$500Delta
Tue, Apr 21 - Sun, Apr 26
Southwest Logo
11:05 am - 6:00 am
HNL
-
MDW
13h 55m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$515Southwest
Fri, May 1 - Mon, May 4
Southwest Logo
11:55 am - 5:40 am
HNL
-
MDW
12h 45m
2 stops
Southwest Logo
11:45 am - 9:05 pm
MDW
-
HNL
14h 20m
2 stops
$551Southwest
Wed, May 6 - Tue, May 12
Southwest Logo
8:00 am - 5:25 am
HNL
-
MDW
16h 25m
1 stop
Southwest Logo
7:30 am - 9:00 pm
MDW
-
HNL
18h 30m
2 stops
$563Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
11:05 am - 6:00 am
HNL
-
MDW
13h 55m
1 stop
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
2 stops
$567Southwest
Fri, May 1 - Mon, May 4
Southwest Logo
9:05 pm - 2:10 pm
HNL
-
MDW
12h 05m
2 stops
Southwest Logo
7:30 am - 9:00 pm
MDW
-
HNL
18h 30m
2 stops
$568Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
2:50 pm - 9:20 pm
MDW
-
HNL
11h 30m
1 stop
$570Southwest
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
8:15 am - 5:55 am
HNL
-
MDW
16h 40m
2 stops
Southwest Logo
5:25 am - 11:45 am
MDW
-
HNL
11h 20m
1 stop
$574Southwest
Tue, Sep 1 - Sun, Sep 20
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
11:10 am - 9:20 pm
MDW
-
HNL
15h 10m
2 stops
$576Southwest
Fri, Sep 18 - Mon, Sep 21

Southwest flights from Honolulu to Chicago Midway Airport

Our best Southwest deals on Honolulu to Chicago Midway Airport flight tickets
Southwest
May 1
HNL11:05 amHonolulu
13h 55m
1 stop
MDW6:00 amChicago Midway
May 4
MDW9:45 pmChicago Midway
17h 05m
1 stop
HNL9:50 amHonolulu
$515
Southwest
May 6
HNL11:55 amHonolulu
12h 45m
2 stops
MDW5:40 amChicago Midway
May 12
MDW11:45 amChicago Midway
14h 20m
2 stops
HNL9:05 pmHonolulu
$551
Southwest
Apr 21
HNL8:00 amHonolulu
16h 25m
1 stop
MDW5:25 amChicago Midway
Apr 28
MDW7:30 amChicago Midway
18h 30m
2 stops
HNL9:00 pmHonolulu
$563

Delta flights from Honolulu to Chicago Midway Airport

Our best Delta deals on Honolulu to Chicago Midway Airport flight tickets
Delta
Apr 21
HNL3:15 pmHonolulu
12h 32m
1 stop
MDW8:47 amChicago Midway
Apr 26
MDW6:00 amChicago Midway
12h 45m
1 stop
HNL1:45 pmHonolulu
$494
Delta
Apr 21
HNL12:25 pmHonolulu
15h 22m
2 stops
MDW8:47 amChicago Midway
Apr 26
MDW6:00 amChicago Midway
12h 45m
1 stop
HNL1:45 pmHonolulu
$500
Delta
Apr 30
HNL3:15 pmHonolulu
12h 32m
1 stop
MDW8:47 amChicago Midway
May 6
MDW9:29 amChicago Midway
17h 16m
2 stops
HNL9:45 pmHonolulu
$615

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 March 28, 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
Quickest round-trip

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 4/21

3:15 pm-8:47 am

1 stop12h 32m

Chicago Midway

Sun 4/26

6:00 am-1:45 pm

1 stop12h 45m

$494

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 4/21

12:25 pm-8:47 am

2 stops15h 22m

Chicago Midway

Sun 4/26

6:00 am-1:45 pm

1 stop12h 45m

$500

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 5/1

11:05 am-6:00 am

1 stop13h 55m

Chicago Midway

Mon 5/4

9:45 pm-9:50 am

1 stop17h 05m

$515

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 5/6

11:55 am-5:40 am

2 stops12h 45m

Chicago Midway

Tue 5/12

11:45 am-9:05 pm

2 stops14h 20m

$551

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 4/21

8:00 am-5:25 am

1 stop16h 25m

Chicago Midway

Tue 4/28

7:30 am-9:00 pm

2 stops18h 30m

$563

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 5/1

11:05 am-6:00 am

1 stop13h 55m

Chicago Midway

Mon 5/4

10:05 am-9:00 pm

2 stops15h 55m

$567

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 4/21

9:05 pm-2:10 pm

2 stops12h 05m

Chicago Midway

Tue 4/28

7:30 am-9:00 pm

2 stops18h 30m

$568

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 9/18

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Mon 9/21

2:50 pm-9:20 pm

1 stop11h 30m

$570

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 9/1

8:15 am-5:55 am

2 stops16h 40m

Chicago Midway

Sun 9/20

5:25 am-11:45 am

1 stop11h 20m

$574

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 9/18

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Mon 9/21

11:10 am-9:20 pm

2 stops15h 10m

$576

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

What is the cheapest airline that flies from Honolulu to Chicago Midway?

Delta and Southwest are the most popular carriers operating from Honolulu to Chicago Midway

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 35m

Direct flights

None
The fastest flight from Honolulu to Chicago Midway Airport takes 11h 35m
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 35m, 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
4,333 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Benton Harbor
Portage
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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.

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