Cheap Flights from Ashland (ASX) to Chicago (ORD)

Popular airlines from Ashland, WI (ASX-John F. Kennedy Memorial) to Chicago O'Hare Intl. Airport (ORD)

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Frequently asked questions

How much does a flight from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight or cheap return flight from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD) 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 Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD)?
Traveling in is a great way to save, as it's the cheapest month for flights between ASX and ORD. You'll usually find the lowest fares during the off-season.
Which airlines fly direct from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD)?
You can't catch a nonstop flight from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD). However, you can seamlessly travel to Chicago without any layovers by leaving from Gogebic County Airport (IWD).
What is the cheapest airline that flies from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from ASX to ORD. Then, sort your results by "Price (lowest to highest)" to snag the best deal available.
How many flights per day from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD)?
Direct flights from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ASX to ORD?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary depending on various factors, such as the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD)?
To touch down at O'Hare Intl. Airport (ORD) without delays, pick a flight that leaves from Ashland, WI (ASX-John F. Kennedy Memorial) 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 Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from ASX to ORD are generally more expensive. For the cheapest rates, start looking for flights as soon as possible. That said, if your travel plans are flexible, you may land a cheap fare right before your journey.
Is it cheaper to book an ASX to ORD flight and hotel package?
You'll generally save money by securing an ASX to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After choosing your preferred flights and accommodations, you can add extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Ashland, WI (ASX-John F. Kennedy Memorial) to O'Hare Intl. Airport (ORD)?
If you reserved your ASX to ORD flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

Travel information

Origin airport
John F. Kennedy Memorial
Destination airport
O'Hare Intl.
Distance
349 mi

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Ashland to Chicago Flights

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

 

The best time to book a flight from Ashland to Chicago

Sunday is one of the best days to book for cheap flights from Ashland 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 Ashland 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 Ashland to Chicago in 2026. 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 Ashland 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 Ashland 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.

 

Ashland to Chicago Flights

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