Cheap Flights from St. Petersburg (PIE) to Chicago (MDW)

Popular airlines from St. Petersburg-Clearwater Intl. Airport (PIE) to Chicago Midway Airport (MDW)

Find available prices by choosing your travel dates.
Flights from St. Petersburg (PIE) to Chicago (MDW)
Origin airport
St. Petersburg-Clearwater Intl.
Destination airport
Midway Intl.
Distance
1000 mi

St. Petersburg to Chicago Flights

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

The best time to book a flight from St. Petersburg to Chicago

Sunday is one of the best days to book for cheap flights from St. Petersburg 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 St. Petersburg 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 St. Petersburg to Chicago 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 St. Petersburg 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 St. Petersburg 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.

Frequently asked questions

How much does a flight from St. Petersburg-Clearwater Intl. Airport (PIE) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from PIE to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from PIE to MDW?
The cheapest flights from PIE to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from St. Petersburg-Clearwater Intl. Airport (PIE) to Midway Intl. Airport (MDW)?
Although St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.) doesn’t offer any direct flights to Midway Intl. Airport (MDW), other airports have nonstop options. Leaving from Tampa Intl. Airport (TPA) will get you to Chicago without any layovers.
What is the cheapest airline that flies from PIE to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from PIE to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from St. Petersburg-Clearwater Intl. Airport (PIE) to Midway Intl. Airport (MDW)?
Nonstop flights from St. Petersburg-Clearwater Intl. Airport (PIE) to Midway Intl. Airport (MDW) 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 dates and click on either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from PIE to MDW?
You’ll generally 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 St. Petersburg-Clearwater Intl. Airport (PIE) to Midway Intl. Airport (MDW)?
To avoid potential delays on the St. Petersburg-Clearwater Intl. Airport (PIE) to Midway Intl. Airport (MDW) route, fly before 3 PM. Later flights have a 22% higher chance of cancellation.**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 St. Petersburg-Clearwater Intl. Airport (PIE) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from PIE to MDW are typically more expensive. For the best rates, start searching for flights well ahead of time. That said, if you’re flexible with your travel dates, it’s possible to land a cheap fare right before your journey.
Is it cheaper to book a PIE to MDW flight and hotel package?
You’ll typically save money by securing a PIE to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s simple to manage everything in one convenient place. After selecting your preferred flights and accommodations, consider adding extras including car rentals, activities and tours.
Can I cancel or change the date of my flight from St. Petersburg-Clearwater Intl. Airport (PIE) to Midway Intl. Airport (MDW)?
Typically, you can cancel or modify your PIE to MDW flight. However, additional fees may apply, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline’s rules and fees on flight changes, or if you want further details, go to our Customer Service portal.

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*Available to One Key members.