HLN - CHI

$225 Find Cheap Flights from Helena to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Helena to Chicago departing on 5/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Helena to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Helena to Chicago, as well as popular online travel agencies
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$329
Delta
Fri 6/5Tue 6/9
HLN - ORD • 1 stop
Cheapest one-way
$225
Alaska Airlines
Sun 5/31
HLN - ORD • 1 stop
Top airlines
Cheapest • from $329 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Helena and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $354 (round-trip)
Shortest trip • 5h 44m (one-way)
Insights
Insights
Insights
Insights
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Helena to Chicago (HLN-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Helena to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Helena to Chicago

Fri, Jun 5 - Tue, Jun 9
Delta Logo
1:03 pm - 9:50 pm
HLN
-
ORD
7h 47m
1 stop
Delta Logo
7:45 am - 12:20 pm
ORD
-
HLN
5h 35m
1 stop
$329Delta
Fri, Jun 5 - Tue, Jun 9
Delta Logo
1:03 pm - 9:50 pm
HLN
-
ORD
7h 47m
1 stop
Delta Logo
11:23 am - 10:31 pm
ORD
-
HLN
12h 08m
2 stops
$334Delta
Wed, Jul 29 - Tue, Aug 4
Delta Logo
5:40 am - 4:23 pm
HLN
-
ORD
9h 43m
2 stops
Delta Logo
2:07 pm - 10:40 pm
ORD
-
HLN
9h 33m
2 stops
$359Delta
Wed, Jul 29 - Tue, Aug 4
Delta Logo
12:55 pm - 9:48 pm
HLN
-
ORD
7h 53m
1 stop
Delta Logo
2:07 pm - 10:40 pm
ORD
-
HLN
9h 33m
2 stops
$409Delta
Wed, Jul 29 - Tue, Aug 4
Delta Logo
5:40 am - 6:25 pm
HLN
-
MDW
11h 45m
2 stops
Delta Logo
1:16 pm - 10:40 pm
MDW
-
HLN
10h 24m
2 stops
$414Delta
Fri, Oct 9 - Mon, Oct 12
Alaska Airlines Logo
4:08 pm - 11:59 pm
HLN
-
ORD
6h 51m
1 stop
Alaska Airlines Logo
6:00 am - 3:31 pm
ORD
-
HLN
10h 31m
1 stop
$419Alaska Airlines
Wed, Jul 29 - Tue, Aug 4
Delta Logo
5:40 am - 6:29 pm
HLN
-
ORD
11h 49m
2 stops
Delta Logo
2:07 pm - 10:40 pm
ORD
-
HLN
9h 33m
2 stops
$464Delta
Fri, Jun 5 - Mon, Jun 8
Alaska Airlines Logo
4:43 pm - 6:20 am
HLN
-
ORD
12h 37m
1 stop
Alaska Airlines Logo
7:49 pm - 4:06 pm
ORD
-
HLN
21h 17m
1 stop
$473Alaska Airlines
Mon, Jun 8 - Wed, Jun 10
Alaska Airlines Logo
4:43 pm - 6:20 am
HLN
-
ORD
12h 37m
1 stop
Alaska Airlines Logo
6:00 am - 4:32 pm
ORD
-
HLN
11h 32m
1 stop
$483Alaska Airlines
Wed, Jul 29 - Tue, Aug 4
Alaska Airlines Logo
5:09 pm - 6:20 am
HLN
-
ORD
12h 11m
1 stop
Alaska Airlines Logo
6:00 am - 4:32 pm
ORD
-
HLN
11h 32m
1 stop
$489Alaska Airlines
Booking Insights

KAYAK's insights & trends for Helena to Chicago flights

Get data-powered insights and trends into flights from Helena to Chicago to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Helena to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Helena to Chicago were found on Delta ($329) and Alaska Airlines ($419).

Good to know

Cheapest flight$225
Flight from Helena to Chicago O'Hare Airport

When to book flights from Helena to Chicago

Are your dates flexible? Find out the best times to travel from Helena to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Helena to Chicago

  • What is the cheapest flight from Helena to Chicago?

    In the last 3 days, the lowest price for a flight from Helena to Chicago was $225 for a one-way ticket and $329 for a round-trip.

  • Do I need a passport to fly between Helena and Chicago?

    No, a passport isn't needed to fly from Helena to Chicago. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Helena to Chicago?

    When flying out of Helena you will be using Helena. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Helena to Chicago?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Helena to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Helena to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Helena to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Helena is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Helena to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Helena with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Helena to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Helena up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Helena to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Helena to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Helena to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9680 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

8.0 ExcellentWendi, Apr 2026
MSP - ORD
Read more United Airlines reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Everything you need to know for your flight from Helena to Chicago

Information on your arrival and departure airports