Cheap Flights from Chicago (MDW) to Gaylord (GLR)

Popular airlines from Chicago Midway Airport (MDW) to Gaylord, MI (GLR-Gaylord Regional)

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Gaylord, MI (GLR-Gaylord Regional) cost?
Lock in a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Gaylord, MI (GLR-Gaylord Regional) 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 Gaylord, MI (GLR-Gaylord Regional)?
Flying in is a good way to save, as it's the cheapest month for flights between MDW and GLR. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Gaylord, MI (GLR-Gaylord Regional)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from MDW to GLR. Then, sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Gaylord, MI (GLR-Gaylord Regional)?
Nonstop flights from Midway Intl. Airport (MDW) to Gaylord, MI (GLR-Gaylord Regional) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to GLR?
You'll typically find Tuesday the quietest day for flights, while Fridays are often 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 Gaylord, MI (GLR-Gaylord Regional)?
Choose a flight from Midway Intl. Airport (MDW) to Gaylord, MI (GLR-Gaylord Regional) that takes off before 3 PM to reduce the likelihood of delays. Later departures have a 22% higher chance of being canceled, on average.**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 Gaylord, MI (GLR-Gaylord Regional) last-minute?
Last-minute fares from MDW to GLR are typically more expensive. To secure the cheapest rates, start searching for flights well ahead of time. That being said, if you can play around with your travel dates, you may land a cheap fare right before your journey.
Is it cheaper to book a MDW to GLR flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to GLR flight and hotel package with Expedia could result in significant savings. Better still, having everything in one convenient place takes the hassle out of planning your trip. Simply pick your flights and select from our extensive range of stays, then personalize your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Gaylord, MI (GLR-Gaylord Regional)?
Typically, you're able to reschedule or cancel your MDW to GLR flight. However, there may be additional fees, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you want more information, head to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Gaylord Regional
Distance
270 mi

Book with confidence

Chicago to Gaylord Flights

The cheapest times to fly from Chicago to Gaylord

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

 

The best time to book a flight from Chicago to Gaylord

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

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 Gaylord 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 Gaylord 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 Gaylord 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 Gaylord Flights

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*Available to One Key members.