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$200 Cheap Flights from Chicago (CHI) to Helena (HLN)

View $200 flight on Wed, Jan 20, 2027

Photo by Bob Webster

Popular airlines from Chicago to Helena, MT (HLN-Helena Regional)

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    • Cheap Flights from Chicago to Helena (CHI-HLN)

    Prices were available within the past 7 days and start at $200 for one-way flights and $389 for roundtrip, for the period specified. Prices and availability are subject to change.

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    One way

    Roundtrip

    Select United flight, departing Wed, Jan 20 from Chicago to Helena, returning Sun, Jan 24, priced at $389 Found 16 hours ago

    Wed, Jan 20 - Sun, Jan 24 · ORD · HLN · Roundtrip

    Select Delta flight, departing Wed, Feb 3 from Chicago to Helena, returning Tue, Feb 9, priced at $389 Found 22 hours ago

    Wed, Feb 3 - Tue, Feb 9 · ORD · HLN · Roundtrip

    Select Alaska Airlines flight, departing Thu, Dec 10 from Chicago to Helena, returning Mon, Dec 14, priced at $394 Found 1 day ago

    Thu, Dec 10 - Mon, Dec 14 · ORD · HLN · Roundtrip

    Select Delta flight, departing Wed, Jan 20 from Chicago to Helena, returning Sun, Jan 24, priced at $399 Found 16 hours ago

    Wed, Jan 20 - Sun, Jan 24 · ORD · HLN · Roundtrip

    Select United flight, departing Wed, Jan 20 from Chicago to Helena, returning Sun, Jan 24, priced at $400 Found 16 hours ago

    Wed, Jan 20 - Sun, Jan 24 · ORD · HLN · Roundtrip

    Select United flight, departing Mon, Mar 29 from Chicago to Helena, returning Sat, Apr 3, priced at $404 Found 3 hours ago

    Mon, Mar 29 - Sat, Apr 3 · ORD · HLN · Roundtrip

    Select Delta flight, departing Mon, Mar 29 from Chicago to Helena, returning Sat, Apr 3, priced at $404 Found 3 hours ago

    Mon, Mar 29 - Sat, A · pr 3 · ORD · HLN · Roundtrip

    Select United flight, departing Wed, Feb 3 from Chicago to Helena, returning Tue, Feb 9, priced at $408 Found 22 hours ago

    Wed, Feb 3 - Tue, Feb 9 · ORD · HLN · Roundtrip

    Select United flight, departing Sat, May 29 from Chicago to Helena, returning Tue, Jun 1, priced at $414 Found 22 hours ago

    Sat, May 29 - Tue, Jun 1 · ORD · HLN · Roundtrip

    Select Bargain Flight flight, departing Tue, Jun 22 from Chicago to Helena, returning Tue, Jun 29, priced at $479 Found 3 days ago

    Tue, Jun 22 - Tue, Jun 29 · ORD · HLN · Roundtrip

    Book with confidence

    Chicago to Helena Flights

    The cheapest times to fly from Chicago to Helena

    On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Helena are during the month of January. You can find some of the cheapest flights from Chicago to Helena with Expedia's search tool and vast selection of airlines.

    The best time to book a flight from Chicago to Helena

    Sunday is one of the best days to book for cheap flights from Chicago to Helena: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

    How to find cheap round-trip tickets from Chicago to Helena

    Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Helena in 2026. You can also book with separate airlines for your outbound and return journeys, from $200 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

    Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Helena flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

    You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Helena airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

    *Terms apply.

    Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

    Travel information

    Origin airportChicago Midway Airport
    Destination airportHelena, MT
    Distance1,240 miles away
    Airlines servingDelta
    Popular airlineDelta
    Roundtrip price$389

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    *Available to One Key members.