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$380+ Cheap flights from Helena (HLN) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$380
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$202
From Helena to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($130 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/216:18 pmHLN - ORD
1 stop11h 06mAlaska Airlines
Thu 10/238:00 amORD - HLN
1 stop10h 41mAlaska Airlines
Deal found 9/14$380
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 10/146:18 pmHLN - ORD
1 stop11h 06mAlaska Airlines
Sat 10/188:00 amORD - HLN
1 stop10h 41mAlaska Airlines
Deal found 9/13$415
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/155:18 pmHLN - ORD
1 stop5h 41mUnited Airlines
Sat 10/1810:53 amORD - HLN
1 stop6h 47mUnited Airlines
Deal found 9/13$433
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 10/175:18 pmHLN - ORD
1 stop5h 41mUnited Airlines
Tue 10/212:17 pmORD - HLN
1 stop7h 43mUnited Airlines
Deal found 9/13$461
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/142:44 pmHLN - ORD
1 stop6h 55mUnited Airlines
Mon 10/205:01 amORD - HLN
1 stop12h 39mUnited Airlines
Deal found 9/13$464
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 10/146:18 pmHLN - ORD
1 stop11h 06mAlaska Airlines
Fri 10/176:00 amORD - HLN
1 stop12h 41mAlaska Airlines
Deal found 9/13$469
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/142:44 pmHLN - ORD
1 stop6h 55mUnited Airlines
Sun 10/195:01 amORD - HLN
1 stop16h 59mUnited Airlines
Deal found 9/13$484
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 10/175:18 pmHLN - ORD
1 stop5h 41mUnited Airlines
Mon 10/205:01 amORD - HLN
1 stop12h 39mUnited Airlines
Deal found 9/13$492
This Delta deal was found by Cheapflights users on 9/13. 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.
Fri 10/171:00 pmHLN - ORD
2 stops20h 20mDelta
Tue 10/217:50 amORD - HLN
1 stop5h 30mDelta
Deal found 9/13$494
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 9/14$506
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/24:02 pmHLN - ORD
1 stop14h 01mAlaska Airlines
Mon 10/66:00 amORD - HLN
1 stop12h 41mAlaska Airlines
Deal found 9/14$512
This Delta deal was found by Cheapflights users on 9/14. 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 10/215:45 amHLN - MDW
2 stops11h 40mDelta
Thu 10/2310:35 amMDW - HLN
2 stops12h 41mDelta
Deal found 9/14$909

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 September 15, 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 10/15

5:18 pm-11:59 pm

1 stop5h 41m

Chicago O'Hare Intl

Sat 10/18

10:53 am-4:40 pm

1 stop6h 47m

$433

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 10/14

5:18 pm-11:59 pm

1 stop5h 41m

Chicago O'Hare Intl

Tue 10/21

2:53 pm-9:00 pm

1 stop7h 07m

$433

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 10/17

5:18 pm-11:59 pm

1 stop5h 41m

Chicago O'Hare Intl

Tue 10/21

2:17 pm-9:00 pm

1 stop7h 43m

$461

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 10/15

5:18 pm-11:59 pm

1 stop5h 41m

Chicago O'Hare Intl

Mon 10/20

5:01 am-4:40 pm

1 stop12h 39m

$464

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 10/14

2:44 pm-10:39 pm

1 stop6h 55m

Chicago O'Hare Intl

Mon 10/20

5:01 am-4:40 pm

1 stop12h 39m

$464

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 10/14

6:18 pm-6:24 am

1 stop11h 06m

Chicago O'Hare Intl

Fri 10/17

6:00 am-5:41 pm

1 stop12h 41m

$469

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 10/14

2:44 pm-10:39 pm

1 stop6h 55m

Chicago O'Hare Intl

Sun 10/19

5:01 am-9:00 pm

1 stop16h 59m

$484

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 10/15

5:18 pm-11:59 pm

1 stop5h 41m

Chicago O'Hare Intl

Sun 10/19

5:01 am-9:00 pm

1 stop16h 59m

$484

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 10/17

5:18 pm-11:59 pm

1 stop5h 41m

Chicago O'Hare Intl

Mon 10/20

5:01 am-4:40 pm

1 stop12h 39m

$492

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 10/17

1:00 pm-10:20 am

2 stops20h 20m

Chicago O'Hare Intl

Tue 10/21

7:50 am-12:20 pm

1 stop5h 30m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 17 results
1
2

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.

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 September 15, 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
8,931 reviews

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,931 reviews
United Airlines
7.4
Good
8,931 reviews

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 United Airlines and Delta fly from Helena to Chicago in about 5h 41m. The time it takes to get you to your destination can typically vary by up to 16h 30m. 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?

    Delta, at $314, was found to be the cheapest airline from Helena to Chicago. An alternate airline flying to your destination would be United Airlines. Users have found that Delta is 33% 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$314Average$354FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$404Average$791FlexibilityNo cancel feeOn-time69%

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