$486 Cheap Flights from Chicago (ORD) to Glendive (GDV)

View $486 flight on Wed, Nov 19, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Glendive, MT (GDV-Dawson Community)

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Cheap Flights from Chicago to Glendive (ORD-GDV)

Prices were available within the past 7 days and start at $486 for one-way flights and $755 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Wed, Nov 19 - Wed, Feb 11
ORD
Chicago
GDV
Glendive
$755 Roundtrip, found 2 days ago
$755
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Nov 19 from Chicago to Glendive, returning Wed, Feb 11, priced at $755 found 2 days ago
Alaska Airlines
Thu, Nov 13 - Mon, Nov 17
ORD
Chicago
GDV
Glendive
$851 Roundtrip, found 5 days ago
$851
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Thu, Nov 13 from Chicago to Glendive, returning Mon, Nov 17, priced at $851 found 5 days ago
Alaska Airlines
Thu, Nov 13 - Mon, Nov 17
ORD
Chicago
GDV
Glendive
$892 Roundtrip, found 5 days ago
$892
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Thu, Nov 13 from Chicago to Glendive, returning Mon, Nov 17, priced at $892 found 5 days ago
Alaska Airlines
Thu, Nov 13 - Mon, Nov 17
ORD
Chicago
GDV
Glendive
$931 Roundtrip, found 5 days ago
$931
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Thu, Nov 13 from Chicago to Glendive, returning Mon, Nov 17, priced at $931 found 5 days ago
Alaska Airlines
Thu, Nov 13 - Mon, Nov 17
ORD
Chicago
GDV
Glendive
$972 Roundtrip, found 5 days ago
$972
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Thu, Nov 13 from Chicago to Glendive, returning Mon, Nov 17, priced at $972 found 5 days ago
Alaska Airlines
Fri, Nov 14 - Tue, Nov 18
ORD
Chicago
GDV
Glendive
$982 Roundtrip, found 3 days ago
$982
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Fri, Nov 14 from Chicago to Glendive, returning Tue, Nov 18, priced at $982 found 3 days ago
Alaska Airlines
Fri, Nov 14 - Tue, Nov 18
ORD
Chicago
GDV
Glendive
$1,011 Roundtrip, found 3 days ago
$1,011
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Fri, Nov 14 from Chicago to Glendive, returning Tue, Nov 18, priced at $1,011 found 3 days ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV) cost?
Snag a cheap one-way flight from $486 or cheap return flight from $755 from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV)?
November is the cheapest month to fly from ORD to GDV. Avoiding peak travel times is often the key to better flight prices.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV)?
To find the cheapest airline that'll fly you from ORD to GDV, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV)?
You'll have to hop on a flight with a layover if you're traveling from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from ORD to GDV?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV)?
To reach Dawson Community Airport (GDV) without delays, choose a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV) last-minute?
Holding off until just before your trip to book your flight from ORD to GDV generally means paying more. While you may come across some last-minute offers, they're not always guaranteed. Be flexible with your travel plans for a better chance of snagging a bargain.
Is it cheaper to book an ORD to GDV flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to GDV flight and hotel package with Expedia could result in significant savings. What's more, having everything in one convenient place will take the hassle out of planning your trip. Just pick your flights and choose from our extensive range of stays, then customize your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Dawson Community Airport (GDV)?
If you reserved your ORD to GDV flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Dawson Community
Roundtrip price
$754
Distance
902 mi

Book with confidence

Chicago to Glendive Flights

The cheapest times to fly from Chicago to Glendive

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 Glendive are during the month of November. You can find some of the cheapest flights from Chicago to Glendive with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Glendive

Sunday is one of the best days to book for cheap flights from Chicago to Glendive: 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 Glendive

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 Glendive in 2025. You can also book with separate airlines for your outbound and return journeys, from $486 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 Glendive 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 Glendive 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.

 

Chicago to Glendive Flights

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*Available to One Key members.