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$433+ Cheap flights from Helena (HLN) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MDW
Dec 11 — Dec 181
Thu 12/11
Thu 12/18
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 November 11, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$433
(Delta)

Popular in

June

Cheapest in

September
Provider with most accurate pricing for Helena-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Helena-Chicago Midway flights.
Search Deals
From Helena to Chicago Midway
Search Deals
Highest demand for flights based on searches. 35% potential increase in price ($247 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($48 potential savings vs. average RT price).
Search Deals

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 November 11, 2025.

This Delta deal was found by Cheapflights users on 11/9. 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 12/145:30 amHLN - MDW
2 stops9h 48mDelta
Mon 12/151:14 pmMDW - HLN
2 stops10h 16mDelta
Deal found 11/9$529
This Delta deal was found by Cheapflights users on 11/9. 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 11/165:30 amHLN - MDW
2 stops11h 38mDelta
Tue 11/251:15 pmMDW - HLN
2 stops10h 15mDelta
Deal found 11/9$932
This Delta deal was found by Cheapflights users on 11/9. 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 11/241:06 pmHLN - MDW
2 stops9h 34mDelta
Fri 11/2810:47 amMDW - HLN
2 stops12h 43mDelta
Deal found 11/9$1,118

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 November 11, 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

Fri 2/27

1:07 pm-4:16 pm

2 stops26h 09m

Chicago Midway

Tue 3/3

1:28 pm-10:29 pm

2 stops10h 01m

$433

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 2/27

1:07 pm-9:08 am

2 stops19h 01m

Chicago Midway

Mon 3/2

6:17 pm-10:29 pm

2 stops29h 12m

$519

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 12/14

5:30 am-4:18 pm

2 stops9h 48m

Chicago Midway

Mon 12/15

1:14 pm-10:30 pm

2 stops10h 16m

$529

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mon 11/24

1:06 pm-11:40 pm

2 stops9h 34m

Chicago Midway

Fri 11/28

10:47 am-10:30 pm

2 stops12h 43m

$1,118

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 5/5

5:45 am-4:25 pm

2 stops9h 40m

$509

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Compare providers for flights from Helena to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Helena to Midway in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Helena-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Helena-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Helena-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Helena-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Helena-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 26h 09m. 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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