Cheap flights from Pittsburgh to Chicago from $109
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pittsburgh to Chicago departing on 5/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Pittsburgh to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Pittsburgh, with most prices found around $242. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Pittsburgh during the month April is also very affordable. Most momondo users find prices during this month for around $260.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Pittsburgh. The lowest ticket price found for a Wednesday departure recently was $373. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Pittsburgh because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $448.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Pittsburgh in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $374 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $418. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Pittsburgh to Chicago Midway flight route?
Fly from Pittsburgh to Chicago Midway for the best Pittsburgh - Chicago Midway flight prices
How many flights depart from Pittsburgh to Chicago Midway Airport on average per day?
As of May 2025, 2 flights take off from Pittsburgh and land in Chicago Midway Airport each day. The most common flight departure time for this route is 6:00AM, with 35% of daily flights taking off at noon.
How many flights depart from Pittsburgh to Chicago Midway Airport on average per week?
As of May 2025, 15 flights take off from Pittsburgh and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
When to book flights from Pittsburgh to Chicago Midway Airport
Cheap Pittsburgh to Chicago Midway Airport (PIT to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Pittsburgh to Chicago Midway Airport
How far is Pittsburgh to Chicago Midway by plane?
The straight-line distance from Pittsburgh to Chicago Midway is 413.5 mi. 1h 25m is a normal flight duration for this route.
When did momondo last update prices for flights from Pittsburgh Airport to Chicago Midway Airport?
Prices for flights from Pittsburgh Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Pittsburgh Airport to Chicago Midway Airport?
There are 2 operators available for flights from Pittsburgh Airport to Chicago Midway Airport as of May 2025.
How old do you have to be to fly from Pittsburgh Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Pittsburgh Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Pittsburgh to Chicago Midway Airport?
Based on momondo bookings for flights between Pittsburgh and Chicago Midway Airport, the leading plane model is Airbus A319, making up 12.86% of the total bookings. Other popular models include Boeing 737 MAX 8 with 11.04%, Boeing 737-800 Passenger/BBJ2 (winglets) with 11.04%, and Embraer 175 (Enhanced Winglets) with 10.50%.
What is the most popular airline from Pittsburgh to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Pittsburgh to Chicago Midway Airport is Southwest, representing 89% of all bookings. The subsequent popular airline is Delta at 11%.
Best airlines flying from Pittsburgh to Chicago Midway Airport
Compare and see reviews for airlines that fly from Pittsburgh to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $126 | Free Cancellation | Rating 8.0 4,294 reviews | |||
| PriceFrom $197 | Free Cancellation | Rating 8.0 7,934 reviews |
Southwest Flights From Pittsburgh to Chicago Midway Airport
The lowest priced Southwest flight from Pittsburgh to Chicago Midway Airport from the last 72 hours was $126. Generally, Southwest has 15 flights on this route every week with an average price of $315. Southwest is rated 8.0/10 by our users.
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Why should I use momondo to find a flight deal from Pittsburgh to Chicago?
It is quick and easy to find Pittsburgh to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Pittsburgh to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Pittsburgh to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Pittsburgh to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Pittsburgh.
I’m not ready to book a flight from Pittsburgh to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Pittsburgh and alert you when they change.