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$248+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$333
(Delta)

One-way from

$248
(Alaska Airlines)

Popular in

June

Cheapest in

September
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 ($247 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($48 potential savings vs. average RT price).
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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 November 12, 2025.

This Delta deal was found by Cheapflights users on 11/9. 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.
Sun 12/145:30 amHLN - ORD
1 stop6h 10mDelta
Mon 12/157:20 amORD - HLN
1 stop6h 05mDelta
Deal found 11/9$353
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:28 pmHLN - ORD
1 stop10h 53mAlaska Airlines
Mon 12/153:05 pmORD - HLN
2 stops27h 46mAlaska Airlines
Deal found 11/9$406
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/222:26 pmHLN - ORD
1 stop8h 33mUnited Airlines
Wed 12/248:08 pmORD - HLN
1 stop18h 37mUnited Airlines
Deal found 11/10$471
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:26 pmHLN - ORD
1 stop8h 33mUnited Airlines
Thu 12/252:31 pmORD - HLN
1 stop8h 00mUnited Airlines
Deal found 11/10$496
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/212:26 pmHLN - ORD
1 stop5h 53mUnited Airlines
Wed 12/241:55 pmORD - HLN
1 stop8h 36mUnited Airlines
Deal found 11/10$503
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/212:26 pmHLN - ORD
1 stop5h 53mUnited Airlines
Thu 12/252:31 pmORD - HLN
1 stop8h 00mUnited Airlines
Deal found 11/10$506
This Delta deal was found by Cheapflights users on 11/9. 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.
Sun 12/145:30 amHLN - MDW
2 stops9h 48mDelta
Mon 12/151:14 pmMDW - HLN
2 stops10h 16mDelta
Deal found 11/9$529
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:26 pmHLN - ORD
1 stop8h 33mUnited Airlines
Wed 12/248:08 pmORD - HLN
1 stop18h 37mUnited Airlines
Deal found 11/10$541
This Delta deal was found by Cheapflights users on 11/10. 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.
Sat 12/201:11 pmHLN - ORD
1 stop7h 25mDelta
Wed 12/246:45 amORD - HLN
2 stops16h 45mDelta
Deal found 11/10$542
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/202:26 pmHLN - ORD
1 stop8h 33mUnited Airlines
Wed 12/248:08 pmORD - HLN
1 stop18h 37mUnited Airlines
Deal found 11/10$563
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:26 pmHLN - ORD
1 stop7h 34mUnited Airlines
Thu 12/252:31 pmORD - HLN
1 stop8h 00mUnited Airlines
Deal found 11/10$576
This Delta deal was found by Cheapflights users on 11/11. 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.
Sun 11/165:30 amHLN - MDW
2 stops10h 08mDelta
Tue 11/2510:47 amMDW - HLN
2 stops12h 43mDelta
Deal found 11/11$949

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 November 12, 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

Sat 1/24

5:30 am-5:56 pm

2 stops11h 26m

Chicago O'Hare Intl

Sat 1/31

7:20 am-12:27 pm

1 stop6h 07m

$338

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 1/24

5:30 am-12:44 pm

1 stop6h 14m

Chicago O'Hare Intl

Fri 1/30

7:20 am-12:27 pm

1 stop6h 07m

$343

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 12/14

5:30 am-12:40 pm

1 stop6h 10m

Chicago O'Hare Intl

Mon 12/15

7:20 am-12:25 pm

1 stop6h 05m

$353

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 2/27

1:07 pm-4:16 pm

2 stops26h 09m

Chicago Midway

Tue 3/3

1:28 pm-10:29 pm

2 stops10h 01m

$433

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 2/27

1:07 pm-4:16 pm

2 stops26h 09m

Chicago Midway

Mon 3/2

10:53 am-10:29 pm

2 stops12h 36m

$443

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 12/22

2:26 pm-11:59 pm

1 stop8h 33m

Chicago O'Hare Intl

Wed 12/24

8:08 pm-1:45 pm

1 stop18h 37m

$471

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 12/14

6:28 pm-1:09 pm

2 stops17h 41m

Chicago O'Hare Intl

Mon 12/15

8:59 pm-5:51 pm

2 stops21h 52m

$477

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 12/24

2:26 pm-11:59 pm

1 stop8h 33m

Chicago O'Hare Intl

Thu 12/25

2:31 pm-9:31 pm

1 stop8h 00m

$496

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 12/21

2:26 pm-9:19 pm

1 stop5h 53m

Chicago O'Hare Intl

Wed 12/24

1:55 pm-9:31 pm

1 stop8h 36m

$503

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 12/22

2:26 pm-11:59 pm

1 stop8h 33m

Chicago O'Hare Intl

Thu 12/25

7:10 am-1:45 pm

1 stop7h 35m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 18 results
1
2

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 November.
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 November is currently the most expensive (average of $298). 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.

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 November 12, 2025.
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.
United Airlines
7.4
Good
9,015 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,015 reviews
United Airlines
7.4
Good
9,015 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 Delta, United Airlines, and Alaska Airlines fly from Helena to Chicago in about 8h 33m. The time it takes to get you to your destination can typically vary by up to 9h 08m. 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 29% 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 November is currently the most expensive (average of $298). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$311Average$529FlexibilityNo cancel feeOn-time69%
DeltaCheapest$314Average$354FlexibilityNo cancel feeOn-timeN/A

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