HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$244+ 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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Helena to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$346
(Alaska Airlines)

One-way from

$244
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$701
From Helena to Chicago (CHI)
Search Deals
One-way flight from Helena to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($133 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 12, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 stop14h 01mAlaska Airlines
Tue 9/28:00 amORD - HLN
1 stop8h 21mAlaska Airlines
Deal found 6/12$346
This Hawaiian Airlines deal was found by Cheapflights users on 6/11. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/184:09 pmHLN - ORD
1 stop6h 50mHawaiian Airlines
Sat 8/236:20 amORD - HLN
1 stop10h 01mHawaiian Airlines
Deal found 6/11$377
This Delta deal was found by Cheapflights users on 6/11. 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
1 stop8h 04mDelta
Sat 8/236:10 amORD - HLN
2 stops7h 10mDelta
Deal found 6/11$383
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/135:39 pmHLN - ORD
1 stop5h 51mUnited Airlines
Mon 8/187:40 pmORD - HLN
2 stops18h 50mUnited Airlines
Deal found 6/10$432
This Delta deal was found by Cheapflights users on 6/12. 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 8/185:50 amHLN - MDW
2 stops10h 47mDelta
Sat 8/231:08 pmMDW - HLN
2 stops10h 05mDelta
Deal found 6/12$784

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 June 12, 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

Fri 8/29

4:02 pm-7:03 am

1 stop14h 01m

Chicago O'Hare Intl

Tue 9/2

8:00 am-3:21 pm

1 stop8h 21m

$346

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 8/18

4:09 pm-11:59 pm

1 stop6h 50m

Chicago O'Hare Intl

Sat 8/23

6:20 am-3:21 pm

1 stop10h 01m

$377

HelenaChicago

HLN - ORD

HLNORD

Helena

Mon 8/18

1:00 pm-10:04 pm

1 stop8h 04m

Chicago O'Hare Intl

Sat 8/23

6:10 am-12:20 pm

2 stops7h 10m

$383

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 8/13

5:39 pm-12:30 am

1 stop5h 51m

Chicago O'Hare Intl

Mon 8/18

7:40 pm-1:30 pm

2 stops18h 50m

$432

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mon 8/18

5:50 am-5:37 pm

2 stops10h 47m

Chicago Midway

Sat 8/23

1:08 pm-10:13 pm

2 stops10h 05m

$784

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 7/19

4:09 pm-5:40 am

1 stop12h 31m

$244

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 6/15

6:20 am-1:21 pm

1 stop6h 01m

$559

HelenaChicago

HLN - ORD

HLNORD

Helena

Sun 6/15

5:44 am-4:46 pm

2 stops10h 02m

$574

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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?

    Alaska Airlines, at $346, was found to be the cheapest airline from Helena to Chicago.Alternate airlines to your destination round-trip include Hawaiian Airlines and Delta. Users have found that Alaska Airlines is 35% 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 Alaska Airlines, which is currently one of the cheapest options available, starting at $244. United Airlines flights start at $559 while deals on Delta start at $574 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 Helena?

Book flights to Helena if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Helena to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Missoula to O'Hare Intl flights
Bozeman to O'Hare Intl flights
Bozeman to Midway flights
Billings to O'Hare Intl flights
Helena to O'Hare Intl flights
Missoula to Midway flights
Billings to Midway flights
Butte to O'Hare Intl flights
Kalispell to O'Hare Intl flights
Bozeman to St. Louis flights
Helena to Midway flights
Great Falls to O'Hare Intl flights
Billings to St. Louis flights
Missoula to Peoria flights
Kalispell to St. Louis flights
Missoula to St. Louis flights
Kalispell to Midway flights
Butte to Midway flights
Great Falls to Midway flights
Butte to St. Louis flights
Helena to St. Louis flights
Missoula to Moline flights
Billings to Evansville flights
Kalispell to Peoria flights
Missoula to Dubuque flights
Bozeman to Dubuque flights
Billings to Moline flights
Helena to Moline flights
Bozeman to Moline flights
Cody to Bloomington flights
Kalispell to Moline flights
Cody to O'Hare Intl flights
Cody to Springfield flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$314Average$524FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$404Average$756FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.