HLN - CHI

$380 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 10/21. 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

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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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

Tue, Oct 21 - Thu, Oct 23
Alaska Airlines Logo
6:18 pm - 6:24 amHLN-ORD
11h 06m1 stop
Alaska Airlines Logo
8:00 am - 5:41 pmORD-HLN
10h 41m1 stop
$380Alaska Airlines
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Tue, Oct 14 - Sat, Oct 18
Alaska Airlines Logo
6:18 pm - 6:24 amHLN-ORD
11h 06m1 stop
Alaska Airlines Logo
8:00 am - 5:41 pmORD-HLN
10h 41m1 stop
$415Alaska Airlines
Find Deal
Tue, Oct 21 - Thu, Oct 23
Alaska Airlines Logo
6:18 pm - 2:50 pmHLN-ORD
19h 32m2 stops
Alaska Airlines Logo
6:00 am - 5:41 pmORD-HLN
12h 41m1 stop
$421Alaska Airlines
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Wed, Oct 15 - Sat, Oct 18
United Airlines Logo
5:18 pm - 11:59 pmHLN-ORD
5h 41m1 stop
United Airlines Logo
10:53 am - 4:40 pmORD-HLN
6h 47m1 stop
$433United Airlines
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Fri, Oct 17 - Sat, Oct 18
United Airlines Logo
5:18 pm - 11:59 pmHLN-ORD
5h 41m1 stop
United Airlines Logo
10:53 am - 4:40 pmORD-HLN
6h 47m1 stop
$461United Airlines
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Tue, Oct 14 - Mon, Oct 20
United Airlines Logo
2:44 pm - 10:39 pmHLN-ORD
6h 55m1 stop
United Airlines Logo
5:01 am - 4:40 pmORD-HLN
12h 39m1 stop
$464United Airlines
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Tue, Oct 14 - Sun, Oct 19
United Airlines Logo
2:44 pm - 10:39 pmHLN-ORD
6h 55m1 stop
United Airlines Logo
5:01 am - 9:00 pmORD-HLN
16h 59m1 stop
$484United Airlines
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Fri, Oct 17 - Tue, Oct 21
Delta Logo
1:00 pm - 10:20 amHLN-ORD
20h 20m2 stops
Delta Logo
7:50 am - 12:20 pmORD-HLN
5h 30m1 stop
$494Delta
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Sat, Nov 22 - Fri, Nov 28
Delta Logo
1:06 pm - 9:25 pmHLN-ORD
7h 19m1 stop
Delta Logo
7:33 am - 12:26 pmORD-HLN
5h 53m1 stop
$548Delta
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Thu, Nov 20 - Sat, Nov 29
Delta Logo
5:33 am - 12:38 pmHLN-ORD
6h 05m1 stop
Delta Logo
7:33 am - 12:26 pmORD-HLN
5h 53m1 stop
$553Delta
Find Deal

Everything you should know

Top airlines
Alaska Airlines
Cheapest • from $380 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$380
Alaska Airlines
Tue 10/21Thu 10/23
HLN - ORD • 1 stop
Cheapest one-way
Multiple Airlines
Mon 9/15
HLN - CHI • multi-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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$380
Best time to beat the crowds with an average 58% drop in price.
Most popular time to fly with an average 18% increase in price.
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 $380 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.

  • Which airline alliances offer flights from Helena to Chicago?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Helena and Chicago, with SkyTeam being the most commonly used for this 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 8929 reviews
7.1Entertainment
8.1Crew
7.3Comfort
6.6Food
7.7Boarding
Airline reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

2.0 MediocreAnonymous, Aug 2025RSW - ORD
Read more United Airlines reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

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

Information on your arrival and departure airports

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