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$324+ 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
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 May 9, 2026.

This Delta deal was found by Cheapflights users on 5/5. 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.
Fri 6/51:03 pm
HLN
-
ORD
1 stop7h 47m
Delta
Tue 6/97:45 am
ORD
-
HLN
1 stop5h 35m
Delta
Deal found 5/5$329
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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 12/54:08 pm
HLN
-
ORD
1 stop6h 51m
Alaska Airlines
Wed 12/98:00 am
ORD
-
HLN
1 stop8h 31m
Alaska Airlines
Deal found 5/7$339
This Delta deal was found by Cheapflights users on 5/6. 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.
Tue 6/25:45 am
HLN
-
ORD
1 stop5h 07m
Delta
Thu 7/27:45 am
ORD
-
HLN
1 stop5h 35m
Delta
Deal found 5/6$354
This United Airlines deal was found by Cheapflights users on 5/7. 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 6/62:20 pm
HLN
-
ORD
1 stop7h 29m
United Airlines
Sat 6/137:05 am
ORD
-
HLN
1 stop7h 28m
United Airlines
Deal found 5/7$389
This deal was found by Cheapflights users on 5/4. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:30 pm
HLN
-
ORD
1 stop7h 14m
United Airlines
Sat 10/318:55 am
ORD
-
HLN
1 stop5h 32m
United Airlines
Deal found 5/4$419
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Wed 9/22:29 pm
HLN
-
ORD
1 stop8h 30m
United Airlines
Sat 9/56:00 am
ORD
-
HLN
1 stop8h 32m
United Airlines
Deal found 5/4$479
This Expedia deal was found by Cheapflights users on 5/7. 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.
Sat 6/64:43 pm
HLN
-
ORD
2 stops26h 16m
Alaska Airlines
Sat 6/136:00 am
ORD
-
HLN
1 stop11h 32m
Alaska Airlines
Deal found 5/7$495
This Delta deal was found by Cheapflights users on 5/7. 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 6/65:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Sat 6/131:49 pm
MDW
-
HLN
2 stops9h 42m
Delta
Deal found 5/7$529
This Delta deal was found by Cheapflights users on 5/5. 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 5/205:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Sun 5/241:59 pm
MDW
-
HLN
2 stops9h 34m
Delta
Deal found 5/5$800
This Delta deal was found by Cheapflights users on 5/5. 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.
Fri 6/55:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Tue 6/91:26 pm
MDW
-
HLN
2 stops10h 05m
Delta
Deal found 5/5$974
This Delta deal was found by Cheapflights users on 5/8. 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 6/25:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Thu 7/21:26 pm
MDW
-
HLN
2 stops10h 05m
Delta
Deal found 5/8$975
This Delta deal was found by Cheapflights users on 5/7. 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 5/225:45 am
HLN
-
MDW
2 stops11h 48m
Delta
Tue 5/261:22 pm
MDW
-
HLN
2 stops10h 11m
Delta
Deal found 5/7$1,219

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 May 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(Delta)

One-way from

$324
(Delta)
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

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 May 9, 2026.
Use the filters below to find and compare flights from Helena to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 6/2

5:45 am-11:52 am

1 stop5h 07m

Chicago O'Hare Intl

Thu 7/2

7:45 am-12:20 pm

1 stop5h 35m

$364

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 6/6

2:20 pm-10:49 pm

1 stop7h 29m

Chicago O'Hare Intl

Sat 6/13

7:05 am-1:33 pm

1 stop7h 28m

$389

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 5/20

1:03 pm-11:59 pm

2 stops9h 56m

Chicago O'Hare Intl

Sun 5/24

11:09 am-10:33 pm

2 stops12h 24m

$499

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 6/25

5:35 am-5:02 pm

2 stops10h 27m

Chicago O'Hare Intl

Sun 6/28

7:45 am-12:20 pm

1 stop5h 35m

$510

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 5/20

2:30 pm-11:56 pm

1 stop8h 26m

Chicago O'Hare Intl

Sun 5/24

6:00 am-1:33 pm

1 stop8h 33m

$514

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sat 6/6

5:45 am-6:33 pm

2 stops11h 48m

Chicago Midway

Sat 6/13

1:49 pm-10:31 pm

2 stops9h 42m

$529

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 7/17

2:20 pm-11:19 pm

1 stop7h 59m

Chicago O'Hare Intl

Tue 7/21

7:05 am-9:20 pm

1 stop15h 15m

$601

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 5/21

2:20 pm-10:49 pm

1 stop7h 29m

Chicago O'Hare Intl

Mon 5/25

7:05 am-1:33 pm

1 stop7h 28m

$642

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 5/22

4:43 pm-1:22 pm

2 stops19h 39m

Chicago O'Hare Intl

Tue 5/26

5:44 pm-4:06 pm

1 stop23h 22m

$711

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 6/14

5:09 pm-6:20 am

1 stop12h 11m

Chicago O'Hare Intl

Wed 6/17

8:05 pm-4:32 pm

1 stop21h 27m

$729

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 30 resultsSorted by cheapest first
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 May.
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
No data available for this route at this time. Please check back soon.

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 May 9, 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
9,692 reviews

Entertainment

7.1

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

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
9,692 reviews
United Airlines
7.4
Good
9,692 reviews

Entertainment

7.1

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

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 Delta and United Airlines fly from Helena to Chicago in about 5h 07m. The time it takes to get you to your destination can typically vary by up to 2h 22m. 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.

See more FAQs

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