Cheap Flights from Chicago (MDW) to Tupelo (TUP)

Popular airlines from Chicago Midway Airport (MDW) to Tupelo, MS (TUP-Tupelo Regional)

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Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Tupelo Regional Airport (TUP) cost?
Snag a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Tupelo Regional Airport (TUP) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Tupelo Regional Airport (TUP)?
The cheapest month to fly from MDW to TUP is , when demand is low. Off-peak season is generally when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Tupelo Regional Airport (TUP)?
To find the cheapest airline flying from MDW to TUP, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Tupelo Regional Airport (TUP)?
You'll need to hop on a flight with a layover when traveling from Midway Intl. Airport (MDW) to Tupelo Regional Airport (TUP). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from MDW to TUP?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can change depending on the time of year, carrier and other factors.*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 Tupelo Regional Airport (TUP)?
To arrive at Tupelo Regional Airport (TUP) on time, book a flight that leaves 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 Tupelo Regional Airport (TUP) last-minute?
Holding off until just before your departure to book your flight from MDW to TUP often results in higher prices. While you might find some last-minute deals, they're not always guaranteed. Allow some flexibility in your schedule to maximize your chances of snagging a bargain.
Is it cheaper to book a MDW to TUP flight and hotel package?
Securing a MDW to TUP flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Select from our impressive range of hotels and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Tupelo Regional Airport (TUP)?
Typically, it's possible to reschedule or cancel your MDW to TUP flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Tupelo Regional
Distance
522 mi

Book with confidence

Book with confidence

Chicago to Tupelo Flights

The cheapest times to fly from Chicago to Tupelo

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

 

The best time to book a flight from Chicago to Tupelo

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

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 Tupelo 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 Tupelo 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 Tupelo 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 Tupelo Flights

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Explore a world of travel with Expedia

*Available to One Key members.