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$414+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MDW
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
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 July 23, 2026.

This Delta deal was found by Cheapflights users on 7/22. 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.
Tue 9/297:15 am
HLN
-
MDW
2 stops10h 04m
Delta
Sat 10/311:35 am
MDW
-
HLN
2 stops11h 54m
Delta
Deal found 7/22$414
This Delta deal was found by Cheapflights users on 7/22. 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.
Fri 8/145:40 am
HLN
-
MDW
2 stops11h 53m
Delta
Mon 8/2410:54 am
MDW
-
HLN
2 stops12h 36m
Delta
Deal found 7/22$744
This Delta deal was found by Cheapflights users on 7/23. 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.
Sat 8/226:50 am
HLN
-
MDW
2 stops10h 11m
Delta
Thu 8/271:25 pm
MDW
-
HLN
2 stops10h 05m
Delta
Deal found 7/23$768
This Delta deal was found by Cheapflights users on 7/18. 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 9/25:40 am
HLN
-
MDW
2 stops10h 19m
Delta
Fri 9/41:25 pm
MDW
-
HLN
2 stops10h 05m
Delta
Deal found 7/18$836
This Delta deal was found by Cheapflights users on 7/20. 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 12/235:45 am
HLN
-
MDW
2 stops10h 05m
Delta
Wed 12/301:05 pm
MDW
-
HLN
2 stops10h 36m
Delta
Deal found 7/20$959
This Delta deal was found by Cheapflights users on 7/19. 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 7/295:40 am
HLN
-
MDW
2 stops11h 45m
Delta
Tue 8/41:25 pm
MDW
-
HLN
2 stops10h 05m
Delta
Deal found 7/19$1,037
This Delta deal was found by Cheapflights users on 7/18. 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 9/25:40 am
HLN
-
MDW
2 stops10h 19m
Delta
Sun 9/610:56 am
MDW
-
HLN
2 stops12h 34m
Delta
Deal found 7/18$1,079

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 July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$414
(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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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 July 23, 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

Tue 9/29

7:15 am-6:19 pm

2 stops10h 04m

Chicago Midway

Sat 10/3

11:35 am-10:29 pm

2 stops11h 54m

$414

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/24

10:54 am-10:30 pm

2 stops12h 36m

$744
Quickest round-trip

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 8/22

6:50 am-6:01 pm

2 stops10h 11m

Chicago Midway

Thu 8/27

1:25 pm-10:30 pm

2 stops10h 05m

$768

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 9/2

5:40 am-4:59 pm

2 stops10h 19m

Chicago Midway

Fri 9/4

1:25 pm-10:30 pm

2 stops10h 05m

$836

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 12/23

5:45 am-4:50 pm

2 stops10h 05m

Chicago Midway

Wed 12/30

1:05 pm-10:41 pm

2 stops10h 36m

$959
Cheapest one-way
Quickest one-way

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

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 10h 04m. 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
Valparaiso
Hammond
Saint Joseph
Porter

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