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$409+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MDW
Jul 11 — Jul 181
Sat 7/11
Sat 7/18
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 June 11, 2026.

This Delta deal was found by Cheapflights users on 6/8. 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.
Thu 10/17:15 am
HLN
-
MDW
2 stops10h 18m
Delta
Mon 10/510:48 am
MDW
-
HLN
2 stops12h 36m
Delta
Deal found 6/8$409
This Delta deal was found by Cheapflights users on 6/8. 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.
Fri 8/145:40 am
HLN
-
MDW
2 stops11h 53m
Delta
Mon 8/241:27 pm
MDW
-
HLN
2 stops10h 03m
Delta
Deal found 6/8$682
This Delta deal was found by Cheapflights users on 6/8. 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.
Fri 7/35:35 am
HLN
-
MDW
2 stops11h 56m
Delta
Sat 7/111:49 pm
MDW
-
HLN
2 stops9h 50m
Delta
Deal found 6/8$779
This Delta deal was found by Cheapflights users on 6/10. 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
Tue 8/181:51 pm
MDW
-
HLN
2 stops9h 39m
Delta
Deal found 6/10$857
This Delta deal was found by Cheapflights users on 6/10. 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 8/135:40 am
HLN
-
MDW
2 stops11h 53m
Delta
Tue 8/181:51 pm
MDW
-
HLN
2 stops9h 39m
Delta
Deal found 6/10$1,109
This Delta deal was found by Cheapflights users on 6/10. 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 8/171:51 pm
MDW
-
HLN
2 stops9h 39m
Delta
Deal found 6/10$1,177
This Delta deal was found by Cheapflights users on 6/8. 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 7/295:40 am
HLN
-
MDW
2 stops11h 45m
Delta
Tue 8/410:54 am
MDW
-
HLN
2 stops12h 36m
Delta
Deal found 6/8$1,369
This Delta deal was found by Cheapflights users on 6/10. 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 8/135:40 am
HLN
-
MDW
2 stops11h 53m
Delta
Mon 8/171:51 pm
MDW
-
HLN
2 stops9h 39m
Delta
Deal found 6/10$1,429
This Delta deal was found by Cheapflights users on 6/10. 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 8/235:40 am
HLN
-
MDW
2 stops9h 35m
Delta
Tue 8/251:27 pm
MDW
-
HLN
2 stops10h 03m
Delta
Deal found 6/10$1,734

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 June 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$409
(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 June 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

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/24

1:27 pm-10:30 pm

2 stops10h 03m

$682

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Tue 8/18

1:51 pm-10:30 pm

2 stops9h 39m

$857

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/17

1:51 pm-10:30 pm

2 stops9h 39m

$1,177

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 7/29

5:40 am-6:25 pm

2 stops11h 45m

Chicago Midway

Tue 8/4

12:46 pm-10:30 pm

2 stops10h 44m

$1,369
Quickest round-trip

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 8/23

5:40 am-4:15 pm

2 stops9h 35m

Chicago Midway

Tue 8/25

1:27 pm-10:30 pm

2 stops10h 03m

$1,734

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 7/26

5:40 am-4:15 pm

2 stops9h 35m

Chicago Midway

Thu 7/30

1:18 pm-10:39 pm

2 stops10h 21m

$1,919
Cheapest one-way

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

$463
Quickest one-way

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 7/4

7:00 am-5:54 pm

2 stops9h 54m

$515

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 8/11

5:09 pm-10:03 pm

3 stops27h 54m

$640

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 8/11

5:40 am-6:33 pm

2 stops11h 53m

$1,356

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

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 11h 53m. 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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