HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$340+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Helena to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 17, 2025.

Round-trip from

$543
(Delta)

One-way from

$340
(Delta)

Popular in

December

Cheapest in

September

Average price

$202
From Helena to Chicago Midway
Search Deals
One-way flight from Helena to Chicago Midway
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/17. 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 10/115:45 amHLN - MDW
2 stops10h 58mDelta
Sat 10/181:11 pmMDW - HLN
2 stops10h 05mDelta
Deal found 9/17$729
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 9/305:45 amHLN - MDW
2 stops10h 50mDelta
Sat 10/41:08 pmMDW - HLN
2 stops10h 06mDelta
Deal found 9/15$868
This Delta deal was found by Cheapflights users on 9/15. 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 11/221:06 pmHLN - MDW
2 stops9h 26mDelta
Mon 12/11:14 pmMDW - HLN
2 stops10h 23mDelta
Deal found 9/15$934
This Delta deal was found by Cheapflights users on 9/17. 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 10/25:45 amHLN - MDW
2 stops11h 50mDelta
Mon 10/61:08 pmMDW - HLN
2 stops10h 08mDelta
Deal found 9/17$978
This Delta deal was found by Cheapflights users on 9/17. 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 10/175:45 amHLN - MDW
2 stops10h 58mDelta
Fri 10/241:08 pmMDW - HLN
2 stops10h 08mDelta
Deal found 9/17$1,018
This Delta deal was found by Cheapflights users on 9/16. 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 10/15:45 amHLN - MDW
2 stops11h 50mDelta
Sun 10/51:08 pmMDW - HLN
2 stops10h 06mDelta
Deal found 9/16$1,158
This Delta deal was found by Cheapflights users on 9/17. 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 9/185:45 amHLN - MDW
2 stops10h 50mDelta
Sat 9/201:08 pmMDW - HLN
2 stops10h 06mDelta
Deal found 9/17$1,228
This Delta deal was found by Cheapflights users on 9/15. 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 11/201:06 pmHLN - MDW
2 stops9h 26mDelta
Sat 11/291:47 pmMDW - HLN
2 stops9h 50mDelta
Deal found 9/15$1,989

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 September 17, 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

12:50 pm-9:46 pm

2 stops31h 56m

Chicago Midway

Mon 3/2

1:05 pm-10:38 pm

2 stops10h 33m

$543

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 10/11

5:45 am-5:43 pm

2 stops10h 58m

Chicago Midway

Sat 10/18

1:11 pm-10:16 pm

2 stops10h 05m

$729

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 9/30

5:45 am-5:35 pm

2 stops10h 50m

Chicago Midway

Sat 10/4

1:08 pm-10:14 pm

2 stops10h 06m

$868

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 11/22

1:06 pm-11:32 pm

2 stops9h 26m

Chicago Midway

Mon 12/1

1:14 pm-10:37 pm

2 stops10h 23m

$934

HelenaChicago

HLN - MDW

HLNMDW

Helena

Thu 10/2

5:45 am-6:35 pm

2 stops11h 50m

Chicago Midway

Mon 10/6

1:08 pm-10:16 pm

2 stops10h 08m

$978

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 10/17

5:45 am-5:43 pm

2 stops10h 58m

Chicago Midway

Fri 10/24

1:08 pm-10:16 pm

2 stops10h 08m

$1,018

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 10/1

5:45 am-6:35 pm

2 stops11h 50m

Chicago Midway

Sun 10/5

1:08 pm-10:14 pm

2 stops10h 06m

$1,158

HelenaChicago

HLN - MDW

HLNMDW

Helena

Thu 11/20

1:06 pm-11:32 pm

2 stops9h 26m

Chicago Midway

Sat 11/29

1:47 pm-10:37 pm

2 stops9h 50m

$1,989

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mon 2/2

12:50 pm-9:46 pm

2 stops31h 56m

$340

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 2/1

12:50 pm-9:46 pm

2 stops31h 56m

$451

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

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 31h 56m. 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.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.