HLN - CHI

$145 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 5/5. 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
$289
United Airlines
Fri 3/20Tue 3/24
HLN - ORD • 1 stop
Cheapest one-way
$145
Delta
Tue 5/5
HLN - ORD • 1 stop
Top airlines
United Airlines
Cheapest • from $289 (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

Fri, Mar 20 - Tue, Mar 24
United Airlines Logo
2:30 pm - 11:52 pm
HLN
-
ORD
8h 22m
1 stop
United Airlines Logo
7:00 am - 1:38 pm
ORD
-
HLN
7h 38m
1 stop
$289United Airlines
Thu, Mar 19 - Wed, Mar 25
United Airlines Logo
2:30 pm - 9:29 pm
HLN
-
ORD
5h 59m
1 stop
United Airlines Logo
2:01 pm - 9:25 pm
ORD
-
HLN
8h 24m
1 stop
$314United Airlines
Sat, Feb 14 - Tue, Feb 17
United Airlines Logo
2:25 pm - 11:59 pm
HLN
-
ORD
8h 34m
1 stop
United Airlines Logo
7:10 am - 1:40 pm
ORD
-
HLN
7h 30m
1 stop
$339United Airlines
Sat, Feb 14 - Tue, Feb 17
United Airlines Logo
2:25 pm - 9:29 pm
HLN
-
ORD
6h 04m
1 stop
United Airlines Logo
7:10 am - 1:40 pm
ORD
-
HLN
7h 30m
1 stop
$374United Airlines
Sat, Feb 14 - Tue, Feb 17
United Airlines Logo
2:25 pm - 9:29 pm
HLN
-
ORD
6h 04m
1 stop
United Airlines Logo
9:25 pm - 9:16 pm
ORD
-
HLN
24h 51m
2 stops
$382United Airlines
Wed, May 20 - Sat, May 23
United Airlines Logo
2:30 pm - 10:58 pm
HLN
-
ORD
7h 28m
1 stop
United Airlines Logo
2:33 pm - 9:05 pm
ORD
-
HLN
7h 32m
1 stop
$383United Airlines
Fri, Mar 6 - Sun, Mar 8
Delta Logo
5:30 am - 12:19 pm
HLN
-
ORD
5h 49m
1 stop
Delta Logo
7:20 am - 12:21 pm
ORD
-
HLN
6h 01m
1 stop
$429Delta
Fri, Mar 20 - Tue, Mar 24
Alaska Airlines Logo
6:22 pm - 11:59 pm
HLN
-
ORD
28h 37m
1 stop
Alaska Airlines Logo
4:10 pm - 5:45 pm
ORD
-
HLN
26h 35m
2 stops
$438Alaska Airlines
Fri, Mar 20 - Tue, Mar 24
Delta Logo
5:30 am - 5:54 pm
HLN
-
MDW
11h 24m
2 stops
Delta Logo
1:10 pm - 10:30 pm
MDW
-
HLN
10h 20m
2 stops
$950Delta
Fri, Jul 24 - Mon, Jul 27
Delta Logo
5:45 am - 6:31 pm
HLN
-
MDW
11h 46m
2 stops
Delta Logo
1:00 pm - 10:34 pm
MDW
-
HLN
10h 34m
2 stops
$1,000Delta
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 United Airlines ($289) and Alaska Airlines ($429).

Find deals

Good to know

Low seasonSeptember
Cheapest flight$145
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 $145 for a one-way ticket and $289 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 9215 reviews
7.7Boarding
8.1Crew
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

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.

4.0 OkaySean, Jan 2026
BOS - ORD
Read more United Airlines reviews

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

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.

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

Information on your arrival and departure airports

Helena (HLN)