Cheap Flights from Chicago (MDW) to Orland (OLA)

Popular airlines from Chicago Midway Airport (MDW) to Orland (OLA-Brekstad)

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Brekstad Airport (OLA) cost?
Lock in a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Brekstad Airport (OLA) 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 Brekstad Airport (OLA)?
The cheapest month to fly from MDW to OLA is , when demand is low. Off-peak months are generally when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Brekstad Airport (OLA)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll fly you from MDW to OLA. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from Midway Intl. Airport (MDW) to Brekstad Airport (OLA)?
Direct flights from Midway Intl. Airport (MDW) to Brekstad Airport (OLA) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to OLA?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*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 Brekstad Airport (OLA)?
To land at Brekstad Airport (OLA) without delays, choose a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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 Brekstad Airport (OLA) last-minute?
Waiting until right before your break to book a ticket from MDW to OLA generally means paying more. While you might find some last-minute deals, they're not always guaranteed. Keep your travel schedule open to maximize your chances of landing a bargain.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Brekstad Airport (OLA)?
In most instances, you're able to cancel or reschedule your MDW to OLA flight. However, there may be additional charges, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you'd like more details, go to our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Brekstad
Distance
3888 mi

Book with confidence

Book with confidence

Chicago to Orland Flights

The cheapest times to fly from Chicago to Orland

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

 

The best time to book a flight from Chicago to Orland

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

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 Orland 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 Orland 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 Orland 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 Orland Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.