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$204+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$396
(Alaska Airlines)

One-way from

$204
(Alaska Airlines)

Popular in

December

Cheapest in

February

Average price

$602
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. 19% potential increase in price ($130 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Alaska Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 8/184:08 pmHLN - ORD
1 stop26h 34mAlaska Airlines
Sat 8/236:20 amORD - HLN
1 stop10h 01mAlaska Airlines
Deal found 5/1$396
This Delta deal was found by Cheapflights users on 4/30. 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.
Tue 8/121:03 pmHLN - ORD
2 stops9h 52mDelta
Wed 8/137:15 amORD - HLN
1 stop6h 20mDelta
Deal found 4/30$482
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/96:45 amHLN - ORD
1 stop13h 25mUnited Airlines
Thu 8/145:00 amORD - HLN
1 stop17h 15mUnited Airlines
Deal found 4/30$507
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 8/75:50 amHLN - MDW
2 stops14h 51mDelta
Thu 8/1410:35 amMDW - HLN
2 stops12h 58mDelta
Deal found 4/30$517

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 May 1, 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

Mon 8/18

4:08 pm-7:42 pm

1 stop26h 34m

Chicago O'Hare Intl

Sat 8/23

6:20 am-3:21 pm

1 stop10h 01m

$396

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 8/12

1:03 pm-11:55 pm

2 stops9h 52m

Chicago O'Hare Intl

Wed 8/13

7:15 am-12:35 pm

1 stop6h 20m

$482

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 8/9

6:45 am-9:10 pm

1 stop13h 25m

Chicago O'Hare Intl

Thu 8/14

5:00 am-9:15 pm

1 stop17h 15m

$507

HelenaChicago

HLN - MDW

HLNMDW

Helena

Thu 8/7

5:50 am-9:41 pm

2 stops14h 51m

Chicago Midway

Thu 8/14

10:35 am-10:33 pm

2 stops12h 58m

$517

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 10/6

4:10 pm-1:04 pm

1 stop19h 54m

$204

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 6/21

5:44 am-5:12 pm

2 stops10h 28m

$335

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 6/21

5:44 am-4:49 pm

2 stops10h 05m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
ExpediaPrice Accuracy1 starTrust 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 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 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, August is the cheapest month in which you can book a flight from Helena to Chicago (average of $245). Flying from Helena to Chicago in March is currently the most expensive (average of $321). 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    Alaska Airlines, at $396, was found to be the cheapest airline from Helena to Chicago.Alternate airlines to your destination round-trip include Delta and United Airlines. Users have found that Alaska Airlines is 26% 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, August is the cheapest month in which you can book a flight from Helena to Chicago (average of $245). Flying from Helena to Chicago in March is currently the most expensive (average of $321). 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 Helena?

Book flights to Helena if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$314Average$524FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$404Average$756FlexibilityNo cancel feeOn-time69%

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