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$339+ Cheap flights from Helena (HLN) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MDW
Mai 27 — Jun 31
Mi 5/27
Mi 6/3
1 adult, Economy
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Cheap flight deals from Helena to Midway

Cheapest flights from Helena to Midway
Explore the most affordable flight options available from Helena to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.

This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 6/65:45 am
HLN
-
MDW
2 stops9h 50m
Delta
Di 6/91:49 pm
MDW
-
HLN
2 stops9h 52m
Delta
Deal found 4/23$359
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 6/65:45 am
HLN
-
MDW
2 stops9h 50m
Delta
Mi 6/101:16 pm
MDW
-
HLN
2 stops10h 25m
Delta
Deal found 4/23$385
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 7/295:40 am
HLN
-
MDW
2 stops11h 45m
Delta
Di 8/41:16 pm
MDW
-
HLN
2 stops10h 24m
Delta
Deal found 4/27$414
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 6/51:03 pm
HLN
-
MDW
2 stops18h 39m
Delta
Di 6/91:49 pm
MDW
-
HLN
2 stops9h 42m
Delta
Deal found 4/25$428
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 6/65:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Mo 6/86:58 pm
MDW
-
HLN
2 stops18h 22m
Delta
Deal found 4/23$465
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 6/51:03 pm
HLN
-
MDW
2 stops27h 53m
Delta
Mi 6/101:16 pm
MDW
-
HLN
2 stops10h 25m
Delta
Deal found 4/23$485
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 10/275:45 am
HLN
-
MDW
2 stops11h 52m
Delta
Sa 10/3110:35 am
MDW
-
HLN
2 stops13h 06m
Delta
Deal found 4/24$518
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 6/41:03 pm
HLN
-
MDW
2 stops22h 39m
Delta
Di 6/91:49 pm
MDW
-
HLN
2 stops9h 52m
Delta
Deal found 4/23$560
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 6/65:45 am
HLN
-
MDW
2 stops11h 48m
Delta
So 6/79:54 am
MDW
-
HLN
2 stops13h 47m
Delta
Deal found 4/22$613
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 6/45:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Mi 6/101:16 pm
MDW
-
HLN
2 stops10h 25m
Delta
Deal found 4/23$662

Find flight deals from Helena to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Helena (HLN) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$359
(Delta)

One-way from

$339
(Delta)
Provider with most accurate pricing for Helena-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Helena-Chicago (CHI) flights.
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From Helena to Chicago Midway
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One-way flight from Helena to Chicago Midway
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Helena to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated April 27, 2026.
Use the filters below to find and compare flights from Helena to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sa 6/6

5:45 am-4:35 pm

2 stops9h 50m

Chicago Midway

Mi 6/10

1:16 pm-10:41 pm

2 stops10h 25m

$385

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mi 7/29

5:40 am-6:25 pm

2 stops11h 45m

Chicago Midway

Di 8/4

1:16 pm-10:40 pm

2 stops10h 24m

$414

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fr 6/5

1:03 pm-8:42 am

2 stops18h 39m

Chicago Midway

Di 6/9

1:49 pm-10:31 pm

2 stops9h 42m

$428

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sa 6/6

5:45 am-6:33 pm

2 stops11h 48m

Chicago Midway

Mo 6/8

6:58 pm-12:20 pm

2 stops18h 22m

$465

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fr 6/5

1:03 pm-5:56 pm

2 stops27h 53m

Chicago Midway

Mi 6/10

1:16 pm-10:41 pm

2 stops10h 25m

$485

HelenaChicago

HLN - MDW

HLNMDW

Helena

Di 5/12

5:45 am-6:33 pm

2 stops11h 48m

Chicago Midway

Sa 5/16

1:22 pm-10:33 pm

2 stops10h 11m

$754

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sa 5/9

5:45 am-6:33 pm

2 stops11h 48m

Chicago Midway

Mi 5/13

1:22 pm-10:33 pm

2 stops10h 11m

$768

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fr 5/8

5:45 am-6:33 pm

2 stops11h 48m

Chicago Midway

So 5/10

10:59 am-10:33 pm

2 stops12h 34m

$874
Cheapest one-way
Quickest one-way

HelenaChicago

HLN - MDW

HLNMDW

Helena

Do 8/20

5:45 am-6:31 pm

2 stops11h 46m

$339

HelenaChicago

HLN - MDW

HLNMDW

Helena

Do 8/20

5:32 pm-10:11 pm

3 stops27h 39m

$646

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Sorted by cheapest first

Best time to book a flight from Helena to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Helena with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Helena to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Helena to Chicago Midway?

    Helena (HLN), located 2.7 mi from the city center, is the airport you fly out of when you book flights from Helena to Chicago Midway. 0 airlines have flights from Helena to Chicago Midway on a regular basis. Booking flights from Helena to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • How long is the flight from Helena to Chicago Midway Airport?

    Departing from Helena to Chicago Midway Airport will take you 9h 50m. The distance from Helena to Chicago Midway Airport is about 1240 mi.

  • Can I find deals for flights from Helena to Midway that include hotel bookings?

    Yes. In addition to deals on Helena to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Helena to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Helena to Midway.

  • Can I find deals for business class flights from Helena to Midway?

    Yes. Cheapflights offers flight deals from Helena to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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