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$240+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Aug 6 — Aug 131
Thu 8/6
Thu 8/13
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 July 7, 2026.

This Delta deal was found by Cheapflights users on 7/6. 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.
Wed 7/295:40 am
HLN
-
ORD
1 stop5h 20m
Delta
Tue 8/41:59 pm
ORD
-
HLN
2 stops9h 31m
Delta
Deal found 7/6$334
This Expedia deal was found by Cheapflights users on 7/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:41 pm
HLN
-
ORD
1 stop11h 59m
Alaska Airlines
Sun 11/159:31 am
ORD
-
HLN
1 stop7h 33m
Alaska Airlines
Deal found 7/2$364
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:45 am
HLN
-
ORD
1 stop5h 40m
Delta
Sun 11/153:50 pm
ORD
-
HLN
2 stops7h 51m
Delta
Deal found 7/2$369
This United Airlines deal was found by Cheapflights users on 7/7. 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.
Tue 9/82:35 pm
HLN
-
ORD
1 stop6h 17m
United Airlines
Tue 9/154:20 pm
ORD
-
HLN
1 stop6h 10m
United Airlines
Deal found 7/7$371
This Delta deal was found by Cheapflights users on 7/4. 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.
Fri 8/1412:55 pm
HLN
-
ORD
1 stop7h 38m
Delta
Mon 8/247:48 am
ORD
-
HLN
1 stop5h 27m
Delta
Deal found 7/4$394
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:20 pm
HLN
-
ORD
1 stop6h 19m
United Airlines
Sat 7/186:00 am
ORD
-
HLN
1 stop8h 33m
United Airlines
Deal found 7/3$434
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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.
Fri 8/145:09 pm
HLN
-
ORD
1 stop12h 11m
Alaska Airlines
Mon 8/246:00 am
ORD
-
HLN
1 stop11h 34m
Alaska Airlines
Deal found 7/7$469
This United Airlines deal was found by Cheapflights users on 7/6. 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 8/142:35 pm
HLN
-
ORD
1 stop6h 25m
United Airlines
Mon 8/243:56 pm
ORD
-
HLN
1 stop6h 34m
United Airlines
Deal found 7/6$479
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:45 am
HLN
-
MDW
2 stops10h 05m
Delta
Sun 11/1512:30 pm
MDW
-
HLN
2 stops11h 11m
Delta
Deal found 7/2$537
This Delta deal was found by Cheapflights users on 7/6. 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.
Wed 7/85:40 am
HLN
-
MDW
2 stops11h 45m
Delta
Fri 8/712:46 pm
MDW
-
HLN
2 stops10h 44m
Delta
Deal found 7/6$859
This Delta deal was found by Cheapflights users on 7/6. 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.
Fri 8/145:40 am
HLN
-
MDW
2 stops11h 53m
Delta
Mon 8/2412:46 pm
MDW
-
HLN
2 stops10h 44m
Delta
Deal found 7/6$961
This Delta deal was found by Cheapflights users on 7/6. 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.
Wed 7/295:40 am
HLN
-
MDW
2 stops11h 45m
Delta
Tue 8/41:25 pm
MDW
-
HLN
2 stops10h 05m
Delta
Deal found 7/6$1,099

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 July 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(Delta)

One-way from

$240
(Alaska Airlines)
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 July 7, 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

Thu 7/23

5:40 am-12:00 pm

1 stop5h 20m

Chicago O'Hare Intl

Tue 7/28

7:45 am-12:15 pm

1 stop5h 30m

$434

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 10/3

4:48 pm-6:20 am

1 stop12h 32m

Chicago O'Hare Intl

Wed 10/7

9:00 am-4:11 pm

1 stop8h 11m

$482

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 8/14

12:55 pm-9:33 pm

1 stop7h 38m

Chicago O'Hare Intl

Mon 8/24

1:50 pm-10:30 pm

2 stops9h 40m

$498

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 7/29

5:09 pm-6:20 am

1 stop12h 11m

Chicago O'Hare Intl

Tue 8/4

8:20 pm-4:32 pm

1 stop21h 12m

$531

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 11/13

5:45 am-4:50 pm

2 stops10h 05m

Chicago Midway

Sun 11/15

12:30 pm-10:41 pm

2 stops11h 11m

$537

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 7/29

5:40 am-12:00 pm

1 stop5h 20m

Chicago O'Hare Intl

Tue 8/4

1:59 pm-10:30 pm

2 stops9h 31m

$554

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/24

12:46 pm-10:30 pm

2 stops10h 44m

$961

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 7/29

5:40 am-6:25 pm

2 stops11h 45m

Chicago Midway

Tue 8/4

1:25 pm-10:30 pm

2 stops10h 05m

$1,198

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mon 8/3

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/10

1:51 pm-10:30 pm

2 stops9h 39m

$1,429

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 8/2

5:40 am-6:25 pm

2 stops11h 45m

Chicago Midway

Sat 8/8

1:25 pm-10:30 pm

2 stops10h 05m

$1,762

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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 July.
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 July 7, 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
9,944 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.7

Entertainment

7.1

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
9,944 reviews
United Airlines
7.4
Good
9,944 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.7

Entertainment

7.1

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 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 Alaska Airlines fly from Helena to Chicago in about 5h 20m. The time it takes to get you to your destination can typically vary by up to 7h 12m. 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
Lansing
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Porter

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