HLN - CHI

$180 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 4/16. 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
$349
Alaska Airlines
Mon 4/13Thu 4/16
HLN - ORD • 1 stop
Cheapest one-way
$180
Alaska Airlines
Thu 4/16
HLN - ORD • 1 stop
Top airlines
Cheapest • from $349 (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 $422 (round-trip)
Shortest trip • 5h 41m (one-way)
Insights
Insights
Insights
Insights
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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!
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

Mon, Apr 13 - Thu, Apr 16
Alaska Airlines Logo
6:22 pm - 6:39 am
HLN
-
ORD
11h 17m
1 stop
Alaska Airlines Logo
6:00 am - 5:45 pm
ORD
-
HLN
12h 45m
1 stop
$349Alaska Airlines
Mon, Apr 13 - Thu, Apr 16
Delta Logo
1:04 pm - 9:18 pm
HLN
-
ORD
7h 14m
1 stop
Delta Logo
1:36 pm - 10:30 pm
ORD
-
HLN
9h 54m
2 stops
$382Delta
Sat, Apr 18 - Wed, Apr 22
Alaska Airlines Logo
6:22 pm - 6:39 am
HLN
-
ORD
11h 17m
1 stop
Alaska Airlines Logo
6:00 am - 5:45 pm
ORD
-
HLN
12h 45m
1 stop
$383Alaska Airlines
Sat, Apr 18 - Wed, Apr 22
Alaska Airlines Logo
6:22 pm - 6:39 am
HLN
-
ORD
11h 17m
1 stop
Alaska Airlines Logo
6:00 am - 5:45 pm
ORD
-
HLN
12h 45m
1 stop
$403Alaska Airlines
Sun, Apr 26 - Thu, Apr 30
Alaska Airlines Logo
6:22 pm - 6:40 am
HLN
-
ORD
11h 18m
1 stop
Alaska Airlines Logo
8:50 am - 5:45 pm
ORD
-
HLN
33h 55m
2 stops
$426Alaska Airlines
Sun, Apr 26 - Thu, Apr 30
Alaska Airlines Logo
6:22 pm - 11:43 pm
HLN
-
ORD
28h 21m
2 stops
Alaska Airlines Logo
6:00 am - 5:45 pm
ORD
-
HLN
12h 45m
1 stop
$441Alaska Airlines
Sat, Mar 28 - Wed, Apr 1
United Airlines Logo
6:15 am - 1:15 pm
HLN
-
ORD
6h 00m
1 stop
United Airlines Logo
8:40 am - 1:39 pm
ORD
-
HLN
5h 59m
1 stop
$485United Airlines
Tue, Mar 31 - Sat, Apr 4
United Airlines Logo
2:25 pm - 10:41 pm
HLN
-
ORD
7h 16m
1 stop
United Airlines Logo
7:00 am - 1:39 pm
ORD
-
HLN
7h 39m
1 stop
$488United Airlines
Sat, Apr 18 - Wed, Apr 22
United Airlines Logo
2:25 pm - 10:58 pm
HLN
-
ORD
7h 33m
1 stop
United Airlines Logo
7:05 am - 9:33 pm
ORD
-
HLN
15h 28m
2 stops
$497United Airlines
Wed, Apr 1 - Sun, Apr 5
Delta Logo
5:30 am - 5:22 pm
HLN
-
MDW
10h 52m
2 stops
Delta Logo
1:10 pm - 10:30 pm
MDW
-
HLN
10h 20m
2 stops
$819Delta
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 Alaska Airlines ($349) and Delta ($382).

Good to know

Cheapest flight$180
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 $180 for a one-way ticket and $349 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 9435 reviews
8.1Crew
6.6Food
7.3Comfort
7.1Entertainment
7.7Boarding
Airline reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

10.0 ExcellentDr. Joseph, Feb 2026
DCA - ORD
Read more United Airlines reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

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

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

Information on your arrival and departure airports