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$139+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap 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 February 5, 2026.

This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:36 pm
HLN
-
ORD
1 stop18h 25m
Alaska Airlines
Fri 3/67:00 am
ORD
-
HLN
1 stop9h 59m
Alaska Airlines
Deal found 2/3$283
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/142:25 pm
HLN
-
ORD
1 stop6h 04m
United Airlines
Tue 2/177:10 am
ORD
-
HLN
1 stop7h 30m
United Airlines
Deal found 2/2$374
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:30 am
HLN
-
ORD
1 stop6h 11m
Delta
Tue 2/101:58 pm
ORD
-
HLN
2 stops9h 31m
Delta
Deal found 2/4$474
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:30 am
HLN
-
MDW
2 stops12h 06m
Delta
Tue 2/1010:48 am
MDW
-
HLN
2 stops12h 41m
Delta
Deal found 2/4$479
This Alaska Airlines deal was found by Cheapflights users on 2/4. 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.
Wed 2/46:48 pm
HLN
-
ORD
1 stop18h 50m
Alaska Airlines
Mon 2/96:06 pm
ORD
-
HLN
1 stop25h 05m
Alaska Airlines
Deal found 2/4$491
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 7/134:59 pm
HLN
-
ORD
1 stop12h 21m
Alaska Airlines
Wed 7/158:00 am
ORD
-
HLN
1 stop9h 22m
Alaska Airlines
Deal found 2/2$510
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:30 am
HLN
-
MDW
2 stops12h 06m
Delta
Mon 2/912:46 pm
MDW
-
HLN
2 stops10h 43m
Delta
Deal found 2/4$684
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:30 am
HLN
-
MDW
2 stops12h 06m
Delta
Sun 2/810:48 am
MDW
-
HLN
2 stops12h 41m
Delta
Deal found 2/4$771
This Delta deal was found by Cheapflights users on 2/3. 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 3/45:30 am
HLN
-
MDW
2 stops11h 15m
Delta
Fri 3/61:29 pm
MDW
-
HLN
2 stops9h 58m
Delta
Deal found 2/3$979

Find 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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$283
(Expedia)

One-way from

$235
(Delta)

Popular in

June

Cheapest in

September

Average price

$306
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. 35% potential increase in price ($247 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 5, 2026.
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 3/4

4:36 pm-12:01 pm

1 stop18h 25m

Chicago O'Hare Intl

Fri 3/6

3:54 pm-3:59 pm

1 stop25h 05m

$283

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 2/17

2:25 pm-10:52 pm

1 stop7h 27m

Chicago O'Hare Intl

Sat 2/21

7:10 am-1:40 pm

1 stop7h 30m

$374

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 3/16

2:30 pm-9:29 pm

1 stop5h 59m

Chicago O'Hare Intl

Fri 3/20

2:45 pm-9:25 pm

1 stop7h 40m

$491

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 7/13

4:59 pm-6:20 am

1 stop12h 21m

Chicago O'Hare Intl

Wed 7/15

8:00 am-4:22 pm

1 stop9h 22m

$510

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 2/17

4:36 pm-1:11 pm

2 stops19h 35m

Chicago O'Hare Intl

Sat 2/21

7:00 am-3:59 pm

1 stop9h 59m

$685

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 3/16

1:02 pm-11:54 pm

2 stops9h 52m

Chicago O'Hare Intl

Fri 3/20

7:20 am-12:21 pm

1 stop6h 01m

$864

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 3/4

5:30 am-5:45 pm

2 stops11h 15m

Chicago Midway

Fri 3/6

1:29 pm-10:27 pm

2 stops9h 58m

$979

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 5/6

1:04 pm-9:18 pm

1 stop7h 14m

$139

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 5/9

1:00 pm-9:50 pm

1 stop7h 50m

$139

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 5/5

5:40 am-11:51 am

1 stop5h 11m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 23 results
1
2
3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub the most. FlightHub 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, October is the cheapest month in which you can book a flight from Helena to Chicago (average of $169). Flying from Helena to Chicago in November is currently the most expensive (average of $298). 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 February 5, 2026.
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
9,236 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,236 reviews
United Airlines
7.4
Good
9,236 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 0 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 Alaska Airlines, United Airlines, and Delta fly from Helena to Chicago in about 7h 27m. The time it takes to get you to your destination can typically vary by up to 10h 58m. 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.

  • 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, October is the cheapest month in which you can book a flight from Helena to Chicago (average of $169). Flying from Helena to Chicago in November is currently the most expensive (average of $298). 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?

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