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$345+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MDW
Apr 10 — Apr 171
Fri 4/10
Fri 4/17
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 March 11, 2026.

This Delta deal was found by Cheapflights users on 3/6. 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 5/95:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Tue 5/121:59 pm
MDW
-
HLN
2 stops9h 34m
Delta
Deal found 3/6$729
This Delta deal was found by Cheapflights users on 3/9. 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 5/45:40 am
HLN
-
MDW
2 stops11h 18m
Delta
Thu 5/71:22 pm
MDW
-
HLN
2 stops10h 11m
Delta
Deal found 3/9$785
This Delta deal was found by Cheapflights users on 3/6. 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 5/85:45 am
HLN
-
MDW
2 stops11h 11m
Delta
Tue 5/121:59 pm
MDW
-
HLN
2 stops9h 34m
Delta
Deal found 3/6$787
This Delta deal was found by Cheapflights users on 3/7. 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 3/215:30 am
HLN
-
MDW
2 stops11h 24m
Delta
Wed 3/2512:47 pm
MDW
-
HLN
2 stops10h 43m
Delta
Deal found 3/7$889
This Delta deal was found by Cheapflights users on 3/9. 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.
Sat 6/135:45 am
HLN
-
MDW
2 stops11h 20m
Delta
Tue 6/161:00 pm
MDW
-
HLN
2 stops10h 34m
Delta
Deal found 3/9$907
This Delta deal was found by Cheapflights users on 3/8. 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.
Wed 6/35:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Sat 6/131:00 pm
MDW
-
HLN
2 stops10h 34m
Delta
Deal found 3/8$1,030
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 3/245:30 am
HLN
-
MDW
2 stops10h 52m
Delta
Sat 3/2810:45 am
MDW
-
HLN
2 stops12h 45m
Delta
Deal found 3/9$1,100
This Delta deal was found by Cheapflights users on 3/9. 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.
Sat 6/135:45 am
HLN
-
MDW
2 stops11h 20m
Delta
Mon 6/152:00 pm
MDW
-
HLN
2 stops9h 34m
Delta
Deal found 3/9$1,350
This Delta deal was found by Cheapflights users on 3/8. 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 3/235:30 am
HLN
-
MDW
2 stops11h 24m
Delta
Fri 3/2712:47 pm
MDW
-
HLN
2 stops10h 43m
Delta
Deal found 3/8$1,550

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 March 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$729
(Delta)

One-way from

$345
(Delta)
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
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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 March 11, 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

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mon 5/4

5:40 am-5:58 pm

2 stops11h 18m

Chicago Midway

Thu 5/7

1:22 pm-10:33 pm

2 stops10h 11m

$785
Quickest round-trip

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 5/8

5:45 am-5:56 pm

2 stops11h 11m

Chicago Midway

Tue 5/12

1:59 pm-10:33 pm

2 stops9h 34m

$787

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 3/21

5:30 am-5:54 pm

2 stops11h 24m

Chicago Midway

Wed 3/25

12:47 pm-10:30 pm

2 stops10h 43m

$889

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 6/13

5:45 am-6:05 pm

2 stops11h 20m

Chicago Midway

Tue 6/16

1:00 pm-10:34 pm

2 stops10h 34m

$907

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 6/3

5:45 am-6:33 pm

2 stops11h 48m

Chicago Midway

Sat 6/13

1:00 pm-10:34 pm

2 stops10h 34m

$1,030

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 3/24

5:30 am-5:22 pm

2 stops10h 52m

Chicago Midway

Sat 3/28

10:45 am-10:30 pm

2 stops12h 45m

$1,100

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 6/13

5:45 am-6:05 pm

2 stops11h 20m

Chicago Midway

Mon 6/15

2:00 pm-10:34 pm

2 stops9h 34m

$1,350

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mon 3/23

5:30 am-5:54 pm

2 stops11h 24m

Chicago Midway

Fri 3/27

12:47 pm-10:30 pm

2 stops10h 43m

$1,550
Cheapest one-way

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 8/30

5:45 am-6:05 pm

2 stops11h 20m

$345

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 3/24

5:30 am-5:22 pm

2 stops10h 52m

$535

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/6

Showing 1-10 of 14 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Helena-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Helena-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 11h 18m. 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
Merrillville
Hammond
Porter
Benton Harbor

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