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

Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between PIE and MDW start from . Book ASAP to get the best price for your journey. Prices and availability are subject to change. Additional terms apply.

Most flights can be cancelled online, but every air carrier has its own set of terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.

Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for St. Pete-Clearwater Intl. Airport to MDW flights, you’ll see a “no change fees” filter for you to select.

It’s around 1,600 kilometres between Clearwater and Chicago, so expect to be in your seat for a while. Keep yourself occupied by packing things like your e-reader or a gripping book.

If you want to travel straight from PIE to Midway Airport, you’ll have to book a flight with one or more stops. Unfortunately, there aren’t any airlines that fly directly on this route.

Booking your trip from St. Petersburg-Clearwater Intl. Airport (PIE) to MDW at the last minute could be your ticket to an awesome deal. However, it could end up costing you a whole lot more! If you’d rather play it safe, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains up to 12 months in advance. If your preferred carrier hasn’t released tickets yet, check back often as deals are updated on Expedia all the time.