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$575+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MDW
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
1 adult, Economy
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Cheap 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 August 16, 2025.

Round-trip from

$727
(Delta)

One-way from

$575
(Delta)

Popular in

December

Cheapest in

September

Average price

$511
From Helena to Chicago Midway
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One-way flight from Helena to Chicago Midway
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Highest demand for flights based on searches. 19% potential increase in price ($126 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 16, 2025.

This Delta deal was found by Cheapflights users on 8/15. 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.
Sat 8/305:50 amHLN - MDW
2 stops10h 47mDelta
Wed 9/310:31 amMDW - HLN
2 stops12h 42mDelta
Deal found 8/15$727
This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 8/305:50 amHLN - MDW
2 stops8h 38mDelta
Tue 9/21:43 pmMDW - HLN
2 stops9h 30mDelta
Deal found 8/14$758
This Delta deal was found by Cheapflights users on 8/15. 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.
Sun 10/195:45 amHLN - MDW
2 stops11h 40mDelta
Sat 11/13:00 pmMDW - HLN
2 stops8h 16mDelta
Deal found 8/15$859
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 8/295:50 amHLN - MDW
2 stops11h 47mDelta
Tue 9/21:43 pmMDW - HLN
2 stops9h 30mDelta
Deal found 8/14$1,009
This Delta deal was found by Cheapflights users on 8/15. 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.
Fri 12/195:40 amHLN - MDW
2 stops11h 27mDelta
Mon 12/2910:08 amMDW - HLN
2 stops13h 34mDelta
Deal found 8/15$1,079
This Delta deal was found by Cheapflights users on 8/14. 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.
Mon 8/185:50 amHLN - MDW
2 stops11h 47mDelta
Sat 8/231:08 pmMDW - HLN
2 stops10h 05mDelta
Deal found 8/14$1,218
This Delta deal was found by Cheapflights users on 8/15. 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.
Thu 8/285:50 amHLN - MDW
2 stops11h 47mDelta
Mon 9/11:08 pmMDW - HLN
2 stops10h 05mDelta
Deal found 8/15$1,299
This Delta deal was found by Cheapflights users on 8/13. 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.
Tue 9/95:50 amHLN - MDW
2 stops10h 47mDelta
Wed 9/101:43 pmMDW - HLN
2 stops9h 30mDelta
Deal found 8/13$2,329

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 August 16, 2025.
Use the filters below to find and compare flights from Helena to Chicago Midway Airport that are best for you.

Fly from

Helena

Fly to

Midway

Route

Depart

Return

Price

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 8/30

5:50 am-5:37 pm

2 stops10h 47m

Chicago Midway

Wed 9/3

10:31 am-10:13 pm

2 stops12h 42m

$727

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 8/30

5:50 am-3:28 pm

2 stops8h 38m

Chicago Midway

Tue 9/2

1:43 pm-10:13 pm

2 stops9h 30m

$758

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 10/19

5:45 am-6:25 pm

2 stops11h 40m

Chicago Midway

Sat 11/1

3:00 pm-10:16 pm

2 stops8h 16m

$859

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/29

5:50 am-6:37 pm

2 stops11h 47m

Chicago Midway

Tue 9/2

1:43 pm-10:13 pm

2 stops9h 30m

$1,009

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 12/19

5:40 am-6:07 pm

2 stops11h 27m

Chicago Midway

Mon 12/29

10:08 am-10:42 pm

2 stops13h 34m

$1,079

HelenaChicago

HLN - MDW

HLNMDW

Helena

Thu 8/28

5:50 am-6:37 pm

2 stops11h 47m

Chicago Midway

Mon 9/1

1:08 pm-10:13 pm

2 stops10h 05m

$1,299

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 9/9

5:50 am-5:37 pm

2 stops10h 47m

Chicago Midway

Wed 9/10

1:43 pm-10:13 pm

2 stops9h 30m

$2,329

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 9/9

5:50 am-5:37 pm

2 stops10h 47m

$575

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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.

  • 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.

  • What is the cheapest month to book a flight from Helena to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Helena to Chicago Midway Airport (average of $160). Flying from Helena to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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