Title: $382 Cheap flights from Wolf Point to Chicago (OLF to ORD) - Expedia.com

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# $382 Cheap Flights from Wolf Point (OLF) to Chicago (ORD)

[View $382 flight on Wed, Mar 25, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:OLF,to:ORD,departure:3/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:381.20&airProductToken=AQqGAQolCLmWARIEMTc2OBjuKiCBWijlyIgDMMfJiAM4UUAAWAFyA1FJUAouCMGmARIEMjA4NBiBWiCSASj1y4gDMPfMiAM4TkABWAFqAk1BcghOSDRPQVNNTgotCMGmARIDNTM4GJIBIK4cKJHOiAMwi9CIAzhOQAFYAWoCTUFyCE5INE9BU01OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) 

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

- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg)  
American Airlines  
[](https://www.expedia.com/Flights-Search?leg1=from:OLF,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:OLF,departure:4/2/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg)  
United  
[](https://www.expedia.com/Flights-Search?leg1=from:OLF,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:OLF,departure:4/2/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg)  
Southwest Airlines  
[](https://www.expedia.com/Flights-Search?leg1=from:OLF,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:OLF,departure:4/2/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg)  
Delta  
[](https://www.expedia.com/Flights-Search?leg1=from:OLF,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:OLF,departure:4/2/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg)  
Frontier Airlines  
[](https://www.expedia.com/Flights-Search?leg1=from:OLF,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:OLF,departure:4/2/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg)  
JetBlue Airways  
[](https://www.expedia.com/Flights-Search?leg1=from:OLF,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:OLF,departure:4/2/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg)  
Alaska Airlines  
[](https://www.expedia.com/Flights-Search?leg1=from:OLF,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:OLF,departure:4/2/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}])

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

Prices were available within the past 7 days and start at $382 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

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## Frequently asked questions

### How much is a flight from OLF to O'Hare Airport?

### Do I need to pay a cancellation fee if I cancel my flight from L. M. Clayton Airport (OLF) to O'Hare Airport?

### How do I find cheap flights from L. M. Clayton Airport (OLF) to O'Hare Intl. Airport (ORD) that have flexible change policies?

### How far is the flight from L. M. Clayton Airport to O'Hare Airport?

### Which airlines fly direct from OLF to O'Hare Airport?

### Are OLF to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?

## 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 2026\. You can also book with separate airlines for your outbound and return journeys, from $382 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](https://www.expedia.com/package-deals). 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.

\*Flight schedules are subject to change.

\*Available to One Key members.