$448+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MDW
Sep 8 — Sep 151
Round-trip
1 adult, Economy
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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
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Best
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One-way
Cheapest flights from Helena to MidwayExplore 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 August 9, 2026.
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 August 9, 2026.
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 11/17:15 am -
2 stops9h 45m
Fri 11/1311:28 am -
2 stops11h 58m
Deal found 8/7![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 8/5. 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 9/127:15 am -
2 stops8h 42m
Tue 9/152:00 pm -
2 stops9h 24m
Deal found 8/5![Delta logo]()
$674
This Delta deal was found by Cheapflights users on 8/5. 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 8/285:40 am -
2 stops11h 53m
Mon 8/3110:54 am -
2 stops12h 36m
Deal found 8/5![Delta logo]()
$689
This Delta deal was found by Cheapflights users on 8/5. 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 9/15:40 am -
2 stops10h 19m
Thu 9/31:51 pm -
2 stops9h 39m
Deal found 8/5![Delta logo]()
$773
This Delta deal was found by Cheapflights users on 8/8. 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 -
2 stops11h 53m
Mon 8/241:25 pm -
2 stops10h 05m
Deal found 8/8![Delta logo]()
$858
This Delta deal was found by Cheapflights users on 8/5. 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 9/35:40 am -
2 stops9h 35m
Wed 9/92:00 pm -
2 stops9h 24m
Deal found 8/5![Delta logo]()
$874
This Delta deal was found by Cheapflights users on 8/6. 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 10/307:15 am -
2 stops8h 32m
Sun 11/11:27 pm -
2 stops9h 57m
Deal found 8/6![Delta logo]()
$1,195
This Delta deal was found by Cheapflights users on 8/7. 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.
Thu 10/157:15 am -
2 stops9h 45m
Mon 10/191:27 pm -
2 stops9h 57m
Deal found 8/7![Delta logo]()
$1,234
This Delta deal was found by Cheapflights users on 8/8. 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 8/135:40 am -
2 stops9h 35m
Sun 8/161:25 pm -
2 stops10h 05m
Deal found 8/8![Delta logo]()
$1,309
This Delta deal was found by Cheapflights users on 8/8. 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 9/35:40 am -
2 stops11h 53m
Tue 9/82:00 pm -
2 stops9h 24m
Deal found 8/8![Delta logo]()
$1,359
Best flights from Helena to MidwayDiscover carefully curated flight deals from Helena to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 9, 2026.
Discover carefully curated flight deals from Helena to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 9, 2026.
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 11/17:15 am -
2 stops9h 45m
Fri 11/1311:28 am -
2 stops11h 58m
Deal found 8/7![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 8/5. 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 9/15:40 am -
2 stops10h 19m
Thu 9/31:51 pm -
2 stops9h 39m
Deal found 8/5![Delta logo]()
$773
This Delta deal was found by Cheapflights users on 8/9. 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.
Thu 9/35:40 am -
2 stops11h 53m
Wed 9/911:35 am -
2 stops11h 49m
Deal found 8/9![Delta logo]()
$874
This Delta deal was found by Cheapflights users on 8/7. 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.
Thu 10/157:15 am -
2 stops9h 45m
Mon 10/191:27 pm -
2 stops9h 57m
Deal found 8/7![Delta logo]()
$1,234
This Delta deal was found by Cheapflights users on 8/8. 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 9/35:40 am -
2 stops11h 53m
Tue 9/82:00 pm -
2 stops9h 24m
Deal found 8/8![Delta logo]()
$1,359
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 10/117:15 am -
2 stops8h 32m
Sun 10/181:27 pm -
2 stops9h 57m
Deal found 8/7![Delta logo]()
$1,609
This Delta deal was found by Cheapflights users on 8/8. 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 9/45:40 am -
2 stops9h 35m
Tue 9/82:00 pm -
2 stops9h 24m
Deal found 8/8![Delta logo]()
$1,920
Last-minute flights from Helena to MidwayDiscover last-minute flight deals from Helena to Midway. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Helena to Midway. Data last updated August 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/8. 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 8/135:40 am -
2 stops9h 35m
Sun 8/161:25 pm -
2 stops10h 05m
Deal found 8/8![Delta logo]()
$1,309
This Delta deal was found by Cheapflights users on 8/8. 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 -
2 stops11h 53m
Mon 8/241:25 pm -
2 stops10h 05m
Deal found 8/8![Delta logo]()
$858
This Delta deal was found by Cheapflights users on 8/8. 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 -
2 stops11h 53m
Sun 8/161:25 pm -
2 stops10h 05m
Deal found 8/8![Delta logo]()
$1,408
This Delta deal was found by Cheapflights users on 8/5. 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 8/285:40 am -
2 stops11h 53m
Mon 8/3110:54 am -
2 stops12h 36m
Deal found 8/5![Delta logo]()
$689
This Delta deal was found by Cheapflights users on 8/5. 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 9/15:40 am -
2 stops10h 19m
Thu 9/31:51 pm -
2 stops9h 39m
Deal found 8/5![Delta logo]()
$773
This Delta deal was found by Cheapflights users on 8/5. 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 9/35:40 am -
2 stops9h 35m
Wed 9/92:00 pm -
2 stops9h 24m
Deal found 8/5![Delta logo]()
$874
This Delta deal was found by Cheapflights users on 8/8. 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 9/35:40 am -
2 stops11h 53m
Tue 9/82:00 pm -
2 stops9h 24m
Deal found 8/8![Delta logo]()
$1,359
This Delta deal was found by Cheapflights users on 8/8. 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 9/45:40 am -
2 stops9h 35m
Tue 9/82:00 pm -
2 stops9h 24m
Deal found 8/8![Delta logo]()
$1,920
This Delta deal was found by Cheapflights users on 8/5. 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 9/127:15 am -
2 stops8h 42m
Tue 9/152:00 pm -
2 stops9h 24m
Deal found 8/5![Delta logo]()
$674
One-way flights from Helena to MidwaySearch for one-way flight options from Helena to Midway. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
Search for one-way flight options from Helena to Midway. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This KAYAK deal was found by Cheapflights users on 8/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:40 am -
2 stops9h 35m
Deal found 8/6![Delta logo]()
$512
This Delta deal was found by Cheapflights users on 8/8. 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 -
2 stops11h 53m
Deal found 8/8![Delta logo]()
$604
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:09 pm -
3 stops23h 52m
Deal found 8/5![Multiple Airlines logo]()
$1,045
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 August 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $448 (Delta) |
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 August 9, 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
Cheapest round-trip
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Sun 11/1
7:15 am-6:00 pm
2 stops9h 45m
Chicago Midway
Fri 11/13
11:28 am-10:26 pm
2 stops11h 58m
$448
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Tue 9/1
5:40 am-4:59 pm
2 stops10h 19m
Chicago Midway
Thu 9/3
1:51 pm-10:30 pm
2 stops9h 39m
$773
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Thu 9/3
5:40 am-6:33 pm
2 stops11h 53m
Chicago Midway
Wed 9/9
11:35 am-10:24 pm
2 stops11h 49m
$874
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Thu 10/15
7:15 am-6:00 pm
2 stops9h 45m
Chicago Midway
Mon 10/19
1:27 pm-10:24 pm
2 stops9h 57m
$1,234
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Thu 9/3
5:40 am-6:33 pm
2 stops11h 53m
Chicago Midway
Tue 9/8
2:00 pm-10:24 pm
2 stops9h 24m
$1,359
Quickest round-trip
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Sun 10/11
7:15 am-4:47 pm
2 stops8h 32m
Chicago Midway
Sun 10/18
1:27 pm-10:24 pm
2 stops9h 57m
$1,609
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Fri 9/4
5:40 am-4:15 pm
2 stops9h 35m
Chicago Midway
Tue 9/8
2:00 pm-10:24 pm
2 stops9h 24m
$1,920
Cheapest one-way
Quickest one-way
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Tue 8/18
5:40 am-4:15 pm
2 stops9h 35m
$512
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Fri 8/14
5:40 am-6:33 pm
2 stops11h 53m
$604
HelenaChicago
HLN Helena - MDW Chicago Midway
HLNMDW
Helena
Tue 8/18
5:09 pm-6:01 pm
3 stops23h 52m
$1,045
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.
HLN-MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
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Valparaiso
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Saint Joseph
Porter
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