Cheap Flights from Chicago (MDW) to Gloucester (GLO)

Popular airlines from Chicago Midway Airport (MDW) to Gloucester (GLO-Gloucestershire)

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Gloucester (GLO-Gloucestershire) cost?
Secure a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Gloucester (GLO-Gloucestershire) 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 Gloucester (GLO-Gloucestershire)?
is the least expensive month to fly from MDW to GLO. Traveling during quieter months is often the key to finding a great deal.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Gloucester (GLO-Gloucestershire)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll take you from MDW to GLO. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Midway Intl. Airport (MDW) to Gloucester (GLO-Gloucestershire)?
There are no daily direct flights departing from Midway Intl. Airport (MDW) to Gloucester (GLO-Gloucestershire). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from MDW to GLO?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary 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 Gloucester (GLO-Gloucestershire)?
To land at Gloucester (GLO-Gloucestershire) on schedule, pick a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The chance 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 Gloucester (GLO-Gloucestershire) last-minute?
Last-minute fares from MDW to GLO are generally more expensive. To lock in the cheapest rates, start looking for flights as soon as possible. That being said, if you can play around with your travel dates, you may land a cheap fare just before your departure.
Is it cheaper to book a MDW to GLO flight and hotel package?
Booking a MDW to GLO flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Pick from our wide range of stays and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Gloucester (GLO-Gloucestershire)?
If you reserved your MDW to GLO flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Gloucestershire
Distance
3869 mi

Book with confidence

Chicago to Gloucester Flights

The cheapest times to fly from Chicago to Gloucester

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

 

The best time to book a flight from Chicago to Gloucester

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

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 Gloucester 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 Chicago to Gloucester 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 Gloucester 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 Gloucester Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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