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$158+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$388
(Delta)

One-way from

$158
(Delta)

Popular in

December

Cheapest in

September

Average price

$506
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 ($126 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
Mon 8/181:00 pmHLN - ORD
2 stops9h 56mDelta
Sat 8/237:45 amORD - HLN
1 stop5h 35mDelta
Deal found 7/29$388
This United Airlines deal was found by Cheapflights users on 7/29. 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 9/22:53 pmORD - HLN
1 stop7h 18mUnited Airlines
Deal found 7/29$463
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 8/294:02 pmHLN - ORD
1 stop29h 02mAlaska Airlines
Tue 9/23:20 pmORD - HLN
1 stop25h 01mAlaska Airlines
Deal found 7/28$514
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/295:50 amHLN - MDW
2 stops10h 47mDelta
Tue 9/21:43 pmMDW - HLN
2 stops9h 30mDelta
Deal found 7/30$639
This United deal was found by Cheapflights users on 7/28. 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.
Mon 8/115:39 pmHLN - ORD
1 stop5h 51mMultiple Airlines
Fri 8/156:00 amORD - HLN
1 stop10h 31mMultiple Airlines
Deal found 7/28$817

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 July 30, 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

1:00 pm-11:56 pm

2 stops9h 56m

Chicago O'Hare Intl

Sat 8/23

7:45 am-12:20 pm

1 stop5h 35m

$388

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 8/29

5:20 pm-11:59 pm

1 stop5h 39m

Chicago O'Hare Intl

Tue 9/2

2:53 pm-9:11 pm

1 stop7h 18m

$463

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 8/29

4:02 pm-10:04 pm

1 stop29h 02m

Chicago O'Hare Intl

Tue 9/2

3:20 pm-3:21 pm

1 stop25h 01m

$514

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/29

5:50 am-5:37 pm

2 stops10h 47m

Chicago Midway

Tue 9/2

1:43 pm-10:13 pm

2 stops9h 30m

$639

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 8/11

5:39 pm-12:30 am

1 stop5h 51m

Chicago O'Hare Intl

Fri 8/15

6:00 am-3:31 pm

1 stop10h 31m

$817

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 8/19

1:00 pm-10:04 pm

1 stop8h 04m

$158

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 8/20

5:50 am-6:37 pm

2 stops11h 47m

$293

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 8/25

4:02 pm-1:09 pm

2 stops20h 07m

$324

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 8/14

5:39 pm-12:30 am

1 stop5h 51m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 30, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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?

    Delta, at $388, was found to be the cheapest airline from Helena to Chicago.Alternate airlines to your destination round-trip include United Airlines and Alaska Airlines. Users have found that Delta is 24% 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 Delta, which is currently one of the cheapest options available, starting at $158. Alaska Airlines flights start at $324 while deals on United Airlines start at $359 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 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$314Average$456FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$404Average$768FlexibilityNo cancel feeOn-time69%

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