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$285+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
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 August 7, 2025.

Round-trip from

$285
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$511
From Helena to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($126 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 7, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/304:02 pmHLN - ORD
1 stop6h 57mHawaiian Airlines
Sat 9/68:00 amORD - HLN
1 stop8h 21mHawaiian Airlines
Deal found 8/6$285
This Delta deal was found by Cheapflights users on 8/5. 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 9/35:50 amHLN - ORD
1 stop5h 08mDelta
Sat 9/137:55 amORD - HLN
1 stop5h 25mDelta
Deal found 8/5$315
This Delta deal was found by Cheapflights users on 8/6. 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 11/11:00 pmHLN - ORD
1 stop7h 43mDelta
Tue 11/46:08 amORD - HLN
2 stops7h 12mDelta
Deal found 8/6$320
This Delta deal was found by Cheapflights users on 8/5. 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 9/41:00 pmHLN - ORD
1 stop7h 00mDelta
Sat 9/137:55 amORD - HLN
1 stop5h 25mDelta
Deal found 8/5$325
This Delta deal was found by Cheapflights users on 8/6. 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 8/305:50 amHLN - ORD
2 stops8h 14mDelta
Sat 9/67:45 amORD - HLN
1 stop5h 35mDelta
Deal found 8/6$340
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/25:20 pmHLN - ORD
1 stop5h 39mUnited Airlines
Sat 9/137:15 amORD - HLN
1 stop7h 15mUnited Airlines
Deal found 8/5$395
This United Airlines deal was found by Cheapflights users on 8/6. 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 8/295:20 pmHLN - ORD
1 stop5h 39mUnited Airlines
Tue 9/28:49 amORD - HLN
1 stop8h 15mUnited Airlines
Deal found 8/6$405
This United Airlines deal was found by Cheapflights users on 8/4. 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 9/55:20 pmHLN - ORD
1 stop5h 39mUnited Airlines
Mon 9/810:56 amORD - HLN
1 stop6h 08mUnited Airlines
Deal found 8/4$411
This United Airlines deal was found by Cheapflights users on 8/5. 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 10/25:18 pmHLN - ORD
1 stop5h 41mUnited Airlines
Mon 10/67:10 amORD - HLN
1 stop7h 59mUnited Airlines
Deal found 8/5$416
This Delta deal was found by Cheapflights users on 8/6. 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 8/305:50 amHLN - MDW
2 stops10h 47mDelta
Sat 9/61:08 pmMDW - HLN
2 stops10h 05mDelta
Deal found 8/6$421
This Alaska Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 9/54:02 pmHLN - ORD
1 stop7h 01mAlaska Airlines
Mon 9/87:00 amORD - HLN
2 stops33h 21mAlaska Airlines
Deal found 8/4$429
This Delta deal was found by Cheapflights users on 8/5. 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 9/21:00 pmHLN - MDW
2 stops19h 16mDelta
Sat 9/131:08 pmMDW - HLN
2 stops10h 06mDelta
Deal found 8/5$507

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 August 7, 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 8/30

4:02 pm-11:59 pm

1 stop6h 57m

Chicago O'Hare Intl

Sat 9/6

8:00 am-3:21 pm

1 stop8h 21m

$285

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 9/17

4:02 pm-12:03 am

1 stop7h 01m

Chicago O'Hare Intl

Wed 9/24

8:00 am-3:21 pm

1 stop8h 21m

$290

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 9/3

5:50 am-11:58 am

1 stop5h 08m

Chicago O'Hare Intl

Sat 9/13

7:55 am-12:20 pm

1 stop5h 25m

$315

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 11/1

1:00 pm-9:43 pm

1 stop7h 43m

Chicago O'Hare Intl

Tue 11/4

6:08 am-12:20 pm

2 stops7h 12m

$320

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 9/4

1:00 pm-9:00 pm

1 stop7h 00m

Chicago O'Hare Intl

Sat 9/13

7:55 am-12:20 pm

1 stop5h 25m

$325

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 8/30

5:50 am-3:04 pm

2 stops8h 14m

Chicago O'Hare Intl

Sat 9/6

7:45 am-12:20 pm

1 stop5h 35m

$340

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 9/2

5:20 pm-11:59 pm

1 stop5h 39m

Chicago O'Hare Intl

Sat 9/13

7:15 am-1:30 pm

1 stop7h 15m

$395

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 9/5

5:20 pm-11:59 pm

1 stop5h 39m

Chicago O'Hare Intl

Mon 9/8

10:56 am-4:04 pm

1 stop6h 08m

$411

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 10/2

5:18 pm-11:59 pm

1 stop5h 41m

Chicago O'Hare Intl

Mon 10/6

7:10 am-2:09 pm

1 stop7h 59m

$416

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 8/30

5:50 am-5:37 pm

2 stops10h 47m

Chicago Midway

Sat 9/6

1:08 pm-10:13 pm

2 stops10h 05m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Showing 1-10 of 24 results
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2
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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 August 7, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and Hawaiian 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Delta
8.0
Very good
7,985 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Hawaiian Airlines
7.8
Good
2,628 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
United Airlines
7.4
Good
8,917 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

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?

    Hawaiian Airlines, at $285, 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 Hawaiian Airlines is 44% 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
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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$314Average$456FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$404Average$768FlexibilityNo cancel feeOn-time69%

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