HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$193+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$335
(Alaska Airlines)

One-way from

$193
(Alaska Airlines)

Popular in

December

Cheapest in

February

Average price

$415
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. 19% potential increase in price ($130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 April 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 5/214:11 pmHLN - ORD
1 stop6h 48mAlaska Airlines
Wed 5/288:00 amORD - HLN
1 stop8h 31mAlaska Airlines
Deal found 4/16$335
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/215:45 amHLN - ORD
1 stop5h 58mDelta
Wed 5/281:45 pmORD - HLN
2 stops9h 31mDelta
Deal found 4/16$352
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Thu 8/76:45 amHLN - ORD
1 stop16h 45mUnited Airlines
Mon 8/115:00 amORD - HLN
1 stop17h 15mUnited Airlines
Deal found 4/16$502
This Hawaiian Airlines deal was found by Cheapflights users on 4/16. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/27:29 pmHLN - ORD
1 stop9h 36mHawaiian Airlines
Tue 5/612:00 pmORD - HLN
1 stop7h 49mHawaiian Airlines
Deal found 4/16$516
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:45 amHLN - MDW
2 stops11h 18mDelta
Mon 8/111:00 pmMDW - HLN
2 stops10h 33mDelta
Deal found 4/16$593
This United deal was found by Cheapflights users on 4/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:00 amHLN - ORD
2 stops9h 08mMultiple Airlines
Mon 9/87:00 amORD - HLN
2 stops9h 34mMultiple Airlines
Deal found 4/16$1,049

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 April 17, 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

Wed 5/21

4:11 pm-11:59 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 5/28

8:00 am-3:31 pm

1 stop8h 31m

$335

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 5/21

5:45 am-12:43 pm

1 stop5h 58m

Chicago O'Hare Intl

Wed 5/28

1:45 pm-10:16 pm

2 stops9h 31m

$352

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 8/7

6:45 am-12:30 am

1 stop16h 45m

Chicago O'Hare Intl

Mon 8/11

5:00 am-9:15 pm

1 stop17h 15m

$502

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 5/2

7:29 pm-6:05 am

1 stop9h 36m

Chicago O'Hare Intl

Tue 5/6

12:00 pm-6:49 pm

1 stop7h 49m

$516

HelenaChicago

HLN - MDW

HLNMDW

Helena

Thu 8/7

5:45 am-6:03 pm

2 stops11h 18m

Chicago Midway

Mon 8/11

1:00 pm-10:33 pm

2 stops10h 33m

$593

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 9/4

7:00 am-5:08 pm

2 stops9h 08m

Chicago O'Hare Intl

Mon 9/8

7:00 am-3:34 pm

2 stops9h 34m

$1,049

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 5/12

7:29 pm-11:59 pm

1 stop27h 30m

$193

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 5/11

5:45 am-12:43 pm

1 stop5h 58m

$280

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 7/30

2:34 pm-10:34 pm

1 stop7h 00m

$284

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 5/11

5:45 am-5:45 pm

2 stops11h 00m

$695

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 April.
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 April 17, 2025.
Alaska Airlines
8.0
Very good
9,887 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,887 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,916 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,380 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $335, 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 37% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Helena to Chicago one-way?

    To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $193. Delta flights start at $280 while deals on United Airlines start at $284 one-way.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Helena to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Bozeman to O'Hare Intl flights
Missoula to O'Hare Intl flights
Kalispell to O'Hare Intl flights
Billings to O'Hare Intl flights
Bozeman to Midway flights
Missoula to Midway flights
Kalispell to Midway flights
Helena to O'Hare Intl flights
Billings to Midway flights
Helena to Midway flights
Bozeman to St. Louis flights
Missoula to St. Louis flights
Great Falls to O'Hare Intl flights
Kalispell to St. Louis flights
Butte to O'Hare Intl flights
Great Falls to Midway flights
Butte to St. Louis flights
Billings to St. Louis flights
Helena to St. Louis flights
Kalispell to Peoria flights
Bozeman to Moline flights
Butte to Midway flights
Missoula to Moline flights
Cody to O'Hare Intl flights
Missoula to Dubuque flights
Helena to Moline flights
Billings to Moline flights
Missoula to Peoria flights
Billings to Evansville flights
Kalispell to Moline flights
Bozeman to Dubuque flights
Cody to Springfield flights
Cody to Bloomington flights

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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$314Average$524FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$404Average$768FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.