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$242+ Cheap flights from Helena (HLN) to Chicago (CHI)

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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap 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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$382
(Alaska Airlines)

One-way from

$242
(Alaska Airlines)

Popular in

June

Cheapest in

September

Average price

$434
Provider with most accurate pricing for Helena-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Helena-Chicago (CHI) flights.
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From Helena to Chicago (CHI)
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One-way flight from Helena to Chicago (CHI)
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Highest demand for flights based on searches. 35% potential increase in price ($243 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($47 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Helena to Chicago

Cheapest flights from Helena to Chicago
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 30, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 11/227:32 pmHLN - ORD
1 stop9h 56mAlaska Airlines
Fri 11/286:00 amORD - HLN
1 stop13h 52mAlaska Airlines
Deal found 10/30$460
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 11/262:22 pmHLN - ORD
1 stop5h 36mUnited Airlines
Wed 12/38:45 amORD - HLN
1 stop6h 02mUnited Airlines
Deal found 10/29$494
This Delta deal was found by Cheapflights users on 10/30. 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 11/225:30 amHLN - ORD
2 stops8h 34mDelta
Fri 11/281:29 pmORD - HLN
2 stops10h 01mDelta
Deal found 10/30$829

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 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Helena to Chicago that are best for you.

Fly from

Helena

Fly to

Chicago

Route

Depart

Return

Price

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 3/1

4:10 pm-5:04 am

1 stop11h 54m

Chicago O'Hare Intl

Wed 3/4

7:45 am-3:43 pm

1 stop8h 58m

$382

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 3/1

4:10 pm-11:59 pm

1 stop6h 49m

Chicago O'Hare Intl

Thu 3/5

7:45 am-3:43 pm

1 stop8h 58m

$402

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 11/22

7:32 pm-6:28 am

1 stop9h 56m

Chicago O'Hare Intl

Fri 11/28

6:00 am-6:52 pm

1 stop13h 52m

$460

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 11/26

2:22 pm-8:58 pm

1 stop5h 36m

Chicago O'Hare Intl

Wed 12/3

8:45 am-1:47 pm

1 stop6h 02m

$494

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 2/27

12:50 pm-3:25 pm

2 stops25h 35m

Chicago Midway

Tue 3/3

10:35 am-10:38 pm

2 stops13h 03m

$548

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 1/8

5:59 pm-11:37 pm

2 stops28h 38m

$242

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 1/8

5:59 pm-7:43 pm

3 stops48h 44m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Helena-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Helena-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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

What is the cheapest month to book a flight from Helena to Chicago?

Currently, October is the cheapest month in which you can book a flight from Helena to Chicago (average of $169). Flying from Helena to Chicago in December is currently the most expensive (average of $312). 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.

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.

  • What airport do you fly from for flights from Helena to Chicago?

    Most people fly from Helena (HLN) if they book a flight from Helena to Chicago. On average, Helena has 0 outbound flights to Chicago per day from 2 airlines. Helena is conveniently located just 2.7 mi from Helena’s city center.

  • How long is the flight from Helena to Chicago?

    Airlines like Alaska Airlines and Delta fly from Helena to Chicago in about 11h 54m. The time it takes to get you to your destination can typically vary by up to 13h 41m. Helena and Chicago are separated by a distance of 1227 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Helena to Chicago round-trip?

    United Airlines, at $311, was found to be the cheapest airline from Helena to Chicago. An alternate airline flying to your destination would be Delta. Users have found that United Airlines is 30% cheaper than the other options available to this destination.

  • Can I find deals for flights from Helena to Chicago that include hotel bookings?

    Yes. In addition to deals on Helena to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Helena to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Helena to Chicago.

  • Can I find deals for business class flights from Helena to Chicago?

    Yes. Cheapflights offers flight deals from Helena to Chicago 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?

    Currently, October is the cheapest month in which you can book a flight from Helena to Chicago (average of $169). Flying from Helena to Chicago in December is currently the most expensive (average of $312). 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?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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Hammond
Porter
Benton Harbor

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Top 2 airlines flying from Helena to Chicago

Discover the top 2 airlines that operate flights from Helena to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$311Average$529FlexibilityNo cancel feeOn-time69%
DeltaCheapest$314Average$354FlexibilityNo cancel feeOn-timeN/A

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