Cheap Flights from Chicago (MDW) to Wolf Point (OLF)

Popular airlines from Chicago Midway Airport (MDW) to Wolf Point, MT (OLF-L. M. Clayton)

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF) cost?
Lock in a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF) 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 Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF)?
The cheapest month to fly from MDW to OLF is , when demand is low. Off-peak season is often when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest MDW to OLF flight.
How many flights per day from Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF)?
Direct flights from Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to OLF?
Typically you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* However, this can change based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF)?
To avoid potential delays on the Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF) route, fly before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**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 Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF) last-minute?
Booking your plane ticket from MDW to OLF shortly before your trip is generally more expensive. However, if you're flexible with your travel times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to OLF flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to OLF flight and hotel package with Expedia could lead to significant savings. What's more, having everything in one easy place takes the hassle out of planning your trip. Simply pick your flights and select from our wide range of hotels, then tailor your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to L. M. Clayton Airport (OLF)?
Typically, it's possible to cancel or reschedule your MDW to OLF flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
L. M. Clayton
Distance
971 mi

Book with confidence

Book with confidence

Chicago to Wolf Point Flights

The cheapest times to fly from Chicago to Wolf Point

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

 

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

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

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

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.