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

Featured airlines

American Airlines
United
Southwest Airlines
Delta
Spirit Airlines
JetBlue Airways
Frontier Airlines
Air India
Hawaiian Airlines

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.
Flights from Chicago (MDW) to St. Petersburg (PIE)
Origin airport
Midway Intl.
Destination airport
St. Petersburg-Clearwater Intl.
Distance
1000 mi

Chicago to St. Petersburg Flights

The cheapest times to fly from Chicago to St. Petersburg

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

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

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

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 St. Petersburg 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 St. Petersburg 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 St. Petersburg 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 Midway Intl. Airport (MDW) to St. Petersburg-Clearwater Intl. Airport (PIE) cost?
Discover the latest flight deals from MDW to PIE 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 MDW to PIE?
The cheapest flights from MDW to PIE are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to PIE?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to PIE. 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 St. Petersburg-Clearwater Intl. Airport (PIE)?
You’ll need to hop on a flight with a layover if you’re traveling from Midway Intl. Airport (MDW) to St. Petersburg-Clearwater Intl. Airport (PIE). Direct flights don’t operate daily on this route. However, simply filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from MDW to PIE?
Friday is generally the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can vary based on a range of factors, including 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 Midway Intl. Airport (MDW) to St. Petersburg-Clearwater Intl. Airport (PIE)?
To touch down at St. Petersburg-Clearwater Intl. Airport (PIE) on schedule, select a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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.
What airports do you fly into for St. Petersburg - Clearwater from Midway Intl. Airport (MDW)?
Hop on a direct flight from Midway Intl. Airport (MDW) to St. Petersburg - Clearwater and touch down at Tampa Intl. Airport (TPA). Another point of entry into this city is Sarasota-Bradenton Intl. Airport (SRQ).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to St. Petersburg-Clearwater Intl. Airport (PIE) last-minute?
Booking your ticket from MDW to PIE right before your trip is generally more expensive. However, if there’s some wiggle room with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to PIE flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to PIE flight and hotel package with Expedia could lead to significant savings. Better still, managing everything in one place takes the hassle out of travel planning. Simply secure your flights and choose from our wide range of stays, then customize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to St. Petersburg-Clearwater Intl. Airport (PIE)?
Generally, it’s possible to cancel or reschedule your MDW to PIE flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline’s policies in your itinerary to see what changes are possible and whether any costs are involved. You’ll also find further details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.