Cheap flights from Chicago to Helena

One-way fares from $254 · CHI → HLN · prices found by travellers in the last 48 hours

Compare all dates Helena → Chicago
Cheapest fare
$254

Alaska Airlines · Fri, Nov 13

Cheapest month
November

from $254

Direct flights
Not recently

Usually 1+ stop

Quickest trip
6h 20m

2,000 km

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Cheapest month to fly from Chicago to Helena

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $254

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Alaska Airlines
Depart09:30 Fri, Nov 13ORD → HLN 6h 20m · 1 stop
$254one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Helena

Where to stay, what to do and getting around, from our travel partners.

Where to stay

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Things to do

Things to do in HelenaTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in HelenaPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in HelenaCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Chicago to Helena

Chicago (CHI) and Helena (HLN) are about 2,000 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 6h 20m. Over the next few months, one-way fares start from $254, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Helena?

The cheapest one-way fare we've seen recently is $254 with Alaska Airlines, departing Friday, November 13, 2026.

What is the cheapest month to fly from Chicago to Helena?

November 2026 currently has the lowest fares, from $254 one way.

Are there direct flights from Chicago to Helena?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Chicago to Helena?

The quickest journey we've seen takes about 6h 20m. Chicago and Helena are around 2,000 km apart.

Which airlines fly from Chicago to Helena?

Recent fares on this route were with Alaska Airlines.

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