Cheap Flights from St. Paul (STP) to Chicago (PWK)

Popular airlines from St. Paul, MN (STP-St. Paul Downtown) to Chicago, IL (PWK-Chicago Executive)

Frequently asked questions

How much does a flight from St. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK) cost?
Get a cheap one-way flight or cheap return flight from St. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from St. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK)?
The cheapest month to fly from STP to PWK is , when there's less demand. Off-peak months are typically when airlines offer lower prices between these airports.
What is the cheapest airline that flies from St. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from STP to PWK. Then, sort your results by "Price (lowest to highest)" to snag the best deal available.
How many flights per day from St. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK)?
You'll have to book a flight with a layover when traveling from St. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from STP to PWK?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can change depending on various factors, such as the time of year and airline.*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. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK)?
To avoid potential delays on the St. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK) route, aim to travel before 3 PM. Departures after this hour are 22% more likely to be canceled.**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. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK) last-minute?
Last-minute fares from STP to PWK are usually more expensive. For the lowest rates, start searching for flights as soon as possible. That said, if you're flexible with your travel plans, you may score a cheap ticket right before your trip.
Is it cheaper to book a STP to PWK flight and hotel package?
Opting for a STP to PWK flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Pick from our wide range of accommodations and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from St. Paul Downtown Airport (STP) to Chicago Executive Airport (PWK)?
In most cases, you can reschedule or cancel your STP to PWK flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you want more details, visit our Customer Service portal.

Travel information

Origin airport
St. Paul Downtown
Destination airport
Chicago Executive
Distance
323 mi

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St. Paul to Chicago Flights

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

 

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

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

 

St. Paul to Chicago Flights

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*Available to One Key members.