HLN - CHI

$357 Find Cheap Flights from Helena to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Helena to Chicago departing on 2/14. 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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Everything you should know

Cheapest round-trip
$357
Alaska Airlines
Sat 2/14Wed 2/18
HLN - ORD • 1 stop
Cheapest one-way
Multiple Airlines
Mon 12/15
HLN - CHI • multi-stop
Top airlines
Alaska Airlines
Cheapest • from $357 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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

Sat, Feb 14 - Wed, Feb 18
Alaska Airlines Logo
4:36 pm - 2:05 pm
HLN
-
ORD
20h 29m1 stop
Alaska Airlines Logo
7:00 am - 3:59 pm
ORD
-
HLN
9h 59m1 stop
$357Alaska Airlines
Sat, Feb 14 - Wed, Feb 18
Alaska Airlines Logo
4:36 pm - 1:11 pm
HLN
-
ORD
19h 35m2 stops
Alaska Airlines Logo
7:00 am - 3:59 pm
ORD
-
HLN
9h 59m1 stop
$447Alaska Airlines
Mon, Mar 23 - Mon, Mar 30
Alaska Airlines Logo
4:10 pm - 11:58 pm
HLN
-
ORD
6h 48m1 stop
Alaska Airlines Logo
7:00 am - 3:38 pm
ORD
-
HLN
9h 38m1 stop
$488Alaska Airlines
Sat, Mar 14 - Thu, Mar 19
United Airlines Logo
2:30 pm - 10:55 pm
HLN
-
ORD
7h 25m1 stop
United Airlines Logo
7:00 am - 1:38 pm
ORD
-
HLN
7h 38m1 stop
$539United Airlines
Sat, Feb 14 - Wed, Feb 18
Alaska Airlines Logo
4:36 pm - 1:11 pm
HLN
-
ORD
19h 35m2 stops
Alaska Airlines Logo
2:07 pm - 3:59 pm
ORD
-
HLN
26h 52m2 stops
$551Alaska Airlines
Mon, Mar 23 - Mon, Mar 30
Alaska Airlines Logo
4:10 pm - 1:07 pm
HLN
-
ORD
19h 57m2 stops
Alaska Airlines Logo
7:00 am - 3:38 pm
ORD
-
HLN
9h 38m1 stop
$566Alaska Airlines
Sat, Mar 14 - Sun, Mar 22
Alaska Airlines Logo
4:36 pm - 2:07 pm
HLN
-
ORD
20h 31m1 stop
Alaska Airlines Logo
7:00 am - 3:38 pm
ORD
-
HLN
9h 38m1 stop
$574Alaska Airlines
Sat, Mar 14 - Thu, Mar 19
Delta Logo
12:59 pm - 9:34 pm
HLN
-
ORD
7h 35m1 stop
Delta Logo
11:15 am - 10:35 pm
ORD
-
HLN
12h 20m2 stops
$664Delta
Sat, Mar 14 - Sun, Mar 22
Delta Logo
12:59 pm - 9:34 pm
HLN
-
ORD
7h 35m1 stop
Delta Logo
3:59 pm - 10:35 pm
ORD
-
HLN
7h 36m2 stops
$914Delta
Sat, Mar 14 - Thu, Mar 19
Delta Logo
5:30 am - 4:49 pm
HLN
-
ORD
10h 19m2 stops
Delta Logo
11:15 am - 10:35 pm
ORD
-
HLN
12h 20m2 stops
$969Delta
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.

What’s the cheapest day of the week to fly from Helena to Chicago?

The average price of all round-trip flights from Helena to Chicago clicked on KAYAK for each day over the last 12 months.

For Helena to Chicago, Wednesday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Chicago back to Helena, the best deals are generally found on Thursday, with Friday being the most expensive.

Good to know

Low seasonSeptember
Cheapest flight$357
Best time to beat the crowds with an average 55% drop in price.
Most popular time to fly and prices are also 4% lower on average.
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 $357 for a round-trip ticket.

  • 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 9092 reviews
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
7.1Entertainment
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

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

Information on your arrival and departure airports