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$167+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:10 amHLN - ORD
1 stop7h 45mUnited Airlines
Sun 1/47:10 amORD - HLN
1 stop7h 35mUnited Airlines
Deal found 12/16$582
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:32 pmHLN - ORD
1 stop28h 27mAlaska Airlines
Sun 1/47:00 amORD - HLN
2 stops11h 55mAlaska Airlines
Deal found 12/16$993

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$347
(Alaska Airlines)

One-way from

$167
(Delta)

Popular in

June

Cheapest in

September

Average price

$424
Provider with most accurate pricing for Helena-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Helena-Chicago (CHI) flights.
Search Deals
From Helena to Chicago (CHI)
Search Deals
One-way flight from Helena to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 35% potential increase in price ($247 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($48 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 18, 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 1/31

6:48 pm-11:50 pm

1 stop28h 02m

Chicago O'Hare Intl

Sat 2/7

8:00 am-6:11 pm

1 stop11h 11m

$347

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 2/14

4:36 pm-4:33 pm

1 stop22h 57m

Chicago O'Hare Intl

Wed 2/18

7:00 am-3:59 pm

1 stop9h 59m

$347

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 3/14

2:30 pm-11:52 pm

1 stop8h 22m

Chicago O'Hare Intl

Thu 3/19

7:00 am-1:38 pm

1 stop7h 38m

$459

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 3/14

12:59 pm-9:34 pm

1 stop7h 35m

Chicago O'Hare Intl

Thu 3/19

9:43 am-10:35 pm

2 stops13h 52m

$494

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 1/31

5:30 am-4:16 pm

2 stops9h 46m

Chicago Midway

Sat 2/7

10:53 am-10:29 pm

2 stops12h 36m

$689

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 3/14

5:30 am-3:25 pm

2 stops8h 55m

Chicago Midway

Thu 3/19

10:49 am-10:35 pm

2 stops12h 46m

$859

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 1/17

1:10 pm-9:52 pm

1 stop7h 42m

$167

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 1/14

5:30 am-1:38 pm

1 stop7h 08m

$167

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 1/18

5:30 am-12:41 pm

1 stop6h 11m

$177

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 1/15

1:10 pm-9:52 pm

1 stop7h 42m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 24 results
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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 December.
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 December 18, 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
9,091 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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
9,091 reviews
United Airlines
7.4
Good
9,091 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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 0 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 9h 46m. The time it takes to get you to your destination can typically vary by up to 18h 16m. Helena and Chicago are separated by a distance of 1240 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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?

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