Cheap flights from Pennsylvania to Chicago from $39
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pennsylvania to Chicago departing on 8/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Pennsylvania to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Southwest flights from Pennsylvania to Chicago Midway Airport
Our best Southwest deals on Pennsylvania to Chicago Midway Airport flight tickets
Delta flights from Pennsylvania to Chicago Midway Airport
Our best Delta deals on Pennsylvania to Chicago Midway Airport flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Pennsylvania 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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Pennsylvania, with most prices found around $138. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Pennsylvania during the month August is also very affordable. Most momondo users find prices during this month for around $144.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Pennsylvania. The lowest ticket price found for a Friday departure recently was $214. 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 Pennsylvania because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $345.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Pennsylvania in the evening is the least expensive time of day to depart. momondo users have found prices as low as $209 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $317. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Pennsylvania to Chicago Midway flight route?
Fly from Philadelphia to Chicago Midway for the best Pennsylvania - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Pennsylvania when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $228 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Pennsylvania for as low as $149 on momondo.
What cabin class options are available on Pennsylvania to Chicago Midway flights?
There are 1 cabin classes available to choose from on Pennsylvania to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Pennsylvania to Chicago Midway?
Southwest, Frontier, and Delta are the most popular carriers operating from Pennsylvania to Chicago Midway
What airlines fly to Chicago Midway Airport?
Frontier, Southwest and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Pennsylvania according to our data. Frontier is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Pennsylvania to Chicago Midway Airport on average per day?
As of June 2025, 16 flights take off from Pennsylvania and land in Chicago Midway Airport each day. The most common flight departure time for this route is 6:00AM, with 34% of daily flights taking off at noon.
How many flights depart from Pennsylvania to Chicago Midway Airport on average per week?
115 flights are operational weekly from Pennsylvania to Chicago Midway Airport as of June 2025. The most popular departure day for this route is Mon, with 21% of flights per week taking off on this day.
Cheap Pennsylvania to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Pennsylvania to Chicago Midway Airport
When did momondo last update prices for flights from Pennsylvania to Chicago Midway Airport?
Prices for flights from Pennsylvania to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Pennsylvania to Chicago Midway Airport?
As of June 2025, there are 5 operators available to choose from for flights from Pennsylvania to Chicago Midway Airport.
How old do you have to be to fly from Pennsylvania to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Pennsylvania to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Pennsylvania to Chicago Midway Airport?
Based on momondo bookings for flights between Pennsylvania and Chicago Midway Airport, the leading plane model is Boeing 737-800, making up 17.98% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.49%, Boeing 737-800 Passenger/BBJ2 (winglets) with 9.78%, and Airbus A320-100/200 with 8.25%.
Best airlines flying from Pennsylvania to Chicago Midway Airport
Compare and see reviews for airlines that fly from Pennsylvania to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $55 | Free Cancellation | Rating 5.9 3,301 reviews | |||
| PriceFrom $126 | Free Cancellation | Rating 8.0 4,280 reviews | |||
| PriceFrom $181 | Free Cancellation | Rating 8.0 7,964 reviews | |||
| PriceFrom $193 | Free Cancellation | Rating 7.4 8,810 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Pennsylvania to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Pennsylvania to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Pennsylvania to Chicago with flexible booking policies on momondo?
All flight searches from Pennsylvania to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Pennsylvania to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Pennsylvania to Chicago.
I’m not ready to book a flight from Pennsylvania to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Pennsylvania are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.