$471 Cheap Flights from Wolf Point (OLF) to Chicago (ORD)

View $471 flight on Mon, Nov 10, 2025Opens in a new window

Popular airlines from Wolf Point, MT (OLF-L. M. Clayton) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Wolf Point to Chicago (OLF-ORD)

Prices were available within the past 7 days and start at $471 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frequently asked questions

How much is a flight from OLF to O'Hare Airport?
The lowest price advertised for a round-trip journey from L. M. Clayton Airport (OLF) to O'Hare Intl. Airport (ORD) is . But you better get a move on. This figure is taken from fares quoted within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from L. M. Clayton Airport (OLF) to O'Hare Airport?
Each air carrier has its own terms and conditions. If you do decide to cancel, follow the simple instructions on our Customer Service Portal.
How do I find cheap flights from L. M. Clayton Airport (OLF) to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for L. M. Clayton Airport to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from L. M. Clayton Airport to O'Hare Airport?
It's around 963 mi from Wolf Point to Chicago, so expect to be up in the air for a while. Keep yourself entertained by packing things like your e-reader or a thrilling novel.
Which airlines fly direct from OLF to O'Hare Airport?
At present, no airlines offer flights directly from L. M. Clayton Airport (OLF) to O'Hare Intl. Airport (ORD). You'll need to book a flight with at least one stop. To get the best price and connections, lock in your airfare ahead of time.
Are OLF to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes score a bargain, with some of the cheapest airfares from OLF to ORD emerging a few weeks prior to the departure date. If you'd rather book ahead of time, Expedia compares and updates the best flight deals continuously — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines publish prices that far in advance.

Travel information

Origin airport
L. M. Clayton
Destination airport
O'Hare Intl.
Distance
957 mi

Book with confidence

Wolf Point to Chicago Flights

The cheapest times to fly from Wolf Point to Chicago

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

 

The best time to book a flight from Wolf Point to Chicago

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

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 Wolf Point to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $471 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 Wolf Point to Chicago 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 Wolf Point to Chicago 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.

 

Wolf Point to Chicago Flights
*Available to One Key members.