$270+ Cheap flights from Helena (HLN) to Chicago (CHI)
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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Nov 12 — Nov 191
Round-trip
1 adult, Economy
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Find cheap flights from Helena to Chicago 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 Chicago
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Best
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Cheapest flights from Helena to ChicagoExplore the most affordable flight options available from Helena to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2026.
Explore the most affordable flight options available from Helena to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2026.
This Delta deal was found by Cheapflights users on 10/11. 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 11/61:08 pm -
1 stop7h 57m
Sun 11/87:35 am -
1 stop5h 53m
Deal found 10/11![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 10/12. 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 10/281:08 pm -
1 stop7h 57m
Mon 11/27:35 am -
1 stop5h 53m
Deal found 10/12![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 10/12. 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 10/271:08 pm -
1 stop7h 57m
Sat 10/317:35 am -
1 stop5h 53m
Deal found 10/12![Delta logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 10/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:41 pm -
1 stop21h 19m
Tue 11/179:30 am -
1 stop7h 34m
Deal found 10/8![Alaska Airlines logo]()
$446
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:23 pm -
1 stop8h 36m
Mon 11/163:56 pm -
1 stop6h 35m
Deal found 10/11![United Airlines logo]()
$508
This Delta deal was found by Cheapflights users on 10/9. 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 10/151:08 pm -
1 stop7h 57m
Mon 10/197:35 am -
1 stop5h 53m
Deal found 10/9![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 10/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:28 am -
2 stops11h 17m
Tue 11/178:40 am -
1 stop6h 00m
Deal found 10/8![United Airlines logo]()
$552
Best flights from Helena to ChicagoDiscover carefully curated flight deals from Helena to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
Discover carefully curated flight deals from Helena to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
This Delta deal was found by Cheapflights users on 10/12. 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 10/281:08 pm -
2 stops9h 49m
Mon 11/27:35 am -
1 stop5h 53m
Deal found 10/12![Delta logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 10/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:41 pm -
1 stop21h 19m
Tue 11/179:30 am -
1 stop7h 34m
Deal found 10/8![Alaska Airlines logo]()
$446
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/236:15 am -
1 stop6h 06m
Wed 1/274:15 pm -
1 stop6h 17m
Deal found 10/9![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 10/12. 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 10/271:08 pm -
1 stop7h 57m
Sat 10/317:35 am -
1 stop5h 53m
Deal found 10/12![Delta logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 10/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/235:00 pm -
1 stop29h 59m
Wed 1/278:00 am -
1 stop9h 23m
Deal found 10/12![Alaska Airlines logo]()
$486
This United Airlines deal was found by Cheapflights users on 10/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:28 am -
2 stops11h 17m
Tue 11/178:40 am -
1 stop6h 00m
Deal found 10/8![United Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 10/11. 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 11/61:08 pm -
2 stops9h 49m
Sun 11/87:35 am -
1 stop5h 53m
Deal found 10/11![Delta logo]()
$534
Last-minute flights from Helena to ChicagoDiscover last-minute flight deals from Helena to Chicago. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Helena to Chicago. Data last updated October 13, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/9. 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 10/151:08 pm -
1 stop7h 57m
Mon 10/197:35 am -
1 stop5h 53m
Deal found 10/9![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 10/12. 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 10/271:08 pm -
1 stop7h 57m
Sat 10/317:35 am -
1 stop5h 53m
Deal found 10/12![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 10/12. 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 10/281:08 pm -
1 stop7h 57m
Mon 11/27:35 am -
1 stop5h 53m
Deal found 10/12![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 10/11. 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 11/61:08 pm -
1 stop7h 57m
Sun 11/87:35 am -
1 stop5h 53m
Deal found 10/11![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:23 pm -
1 stop8h 36m
Mon 11/163:56 pm -
1 stop6h 35m
Deal found 10/11![United Airlines logo]()
$508
This Alaska Airlines deal was found by Cheapflights users on 10/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:41 pm -
1 stop21h 19m
Tue 11/179:30 am -
1 stop7h 34m
Deal found 10/8![Alaska Airlines logo]()
$446
This United Airlines deal was found by Cheapflights users on 10/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:28 am -
2 stops11h 17m
Tue 11/178:40 am -
1 stop6h 00m
Deal found 10/8![United Airlines logo]()
$552
One-way flights from Helena to ChicagoSearch for one-way flight options from Helena to Chicago. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
Search for one-way flight options from Helena to Chicago. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
This Travelocity deal was found by Cheapflights users on 10/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:26 pm -
1 stop11h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Alaska Airlines logo]()
$270
This Alaska Airlines deal was found by Cheapflights users on 10/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:41 pm -
1 stop11h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Alaska Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 10/8. 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 10/291:08 pm -
2 stops9h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/136:20 am -
1 stop6h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![United Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:26 pm -
3 stops47h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$675
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:28 am -
2 stops9h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![United Airlines logo]()
$848
Find flight deals from Helena to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Helena (HLN) to Chicago (CHI). 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 October 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $389 (Delta) |
One-way from | $270 (Travelocity) |
Cheapflights Fare Finder
Customize your flight search to find flights from Helena to Chicago 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 7,457,451 searches. Data last updated October 13, 2026.
Use the filters below to find and compare flights from Helena to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Thu 10/29
5:26 pm-5:40 am
1 stop11h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$270
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Fri 11/13
4:41 pm-5:40 am
1 stop11h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$307
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Thu 10/29
1:08 pm-11:57 pm
2 stops9h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$344
Quickest round-trip
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Sun 12/13
6:20 am-1:30 pm
1 stop6h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$390
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Wed 10/28
1:08 pm-11:57 pm
2 stops9h 49m
Chicago O'Hare Intl
Mon 11/2
7:35 am-12:28 pm
1 stop5h 53m
$399
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Tue 10/27
1:08 pm-10:05 pm
1 stop7h 57m
Chicago O'Hare Intl
Sat 10/31
7:35 am-12:28 pm
1 stop5h 53m
$429
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Sat 11/14
4:41 pm-3:00 pm
1 stop21h 19m
Chicago O'Hare Intl
Tue 11/17
9:30 am-4:04 pm
1 stop7h 34m
$446
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Sat 1/23
6:15 am-1:21 pm
1 stop6h 06m
Chicago O'Hare Intl
Wed 1/27
4:15 pm-9:32 pm
1 stop6h 17m
$469
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Sat 1/23
5:00 pm-11:59 pm
1 stop29h 59m
Chicago O'Hare Intl
Wed 1/27
8:00 am-4:23 pm
1 stop9h 23m
$486
HelenaChicago
HLN Helena - ORD Chicago O'Hare Intl
HLNORD
Helena
Fri 11/6
1:08 pm-11:57 pm
2 stops9h 49m
Chicago O'Hare Intl
Sun 11/8
7:35 am-12:28 pm
1 stop5h 53m
$534
Showing 1-10 of 12 resultsSorted by cheapest first
Compare providers for flights from Helena to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Helena to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Helena-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Helena-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Helena-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Helena-Chicago 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 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 Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Helena with our price prediction graph.
HLN-CHI
HLN-ORD
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.
Cheapflights Insights
Everything you need to know about your flight from Helena to Chicago
HLN-CHI
HLN-ORD
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated October 13, 2026.
Peruse reviews from past customers who have flown with United Airlines from Helena to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Overall
7.4
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Overall
7.4
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Helena to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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