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$69 Cheap Flights from Pittsburgh (PIT) to Chicago (MDW)

View $69 flight on Fri, Sep 11, 2026Opens in a new window

Popular airlines from Pittsburgh Intl. Airport (PIT) to Chicago Midway Airport (MDW)

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Cheap Flights from Pittsburgh to Chicago (PIT-MDW)

Prices were available within the past 7 days and start at $69 for one-way flights and $137 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Aug 13 - Mon, Aug 17
PIT
Pittsburgh
MDW
Chicago
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Aug 13 from Pittsburgh to Chicago, returning Mon, Aug 17, priced at $137 found 1 day ago
Southwest Airlines
Thu, Aug 13 - Mon, Aug 17
PIT
Pittsburgh
MDW
Chicago
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Aug 13 from Pittsburgh to Chicago, returning Mon, Aug 17, priced at $147 found 1 day ago
Southwest Airlines
Thu, Oct 1 - Mon, Oct 5
PIT
Pittsburgh
MDW
Chicago
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Oct 1 from Pittsburgh to Chicago, returning Mon, Oct 5, priced at $158 found 1 day ago
Southwest Airlines
Wed, Sep 2 - Sat, Sep 5
PIT
Pittsburgh
MDW
Chicago
$159 Roundtrip, found 8 hours ago
$159
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Pittsburgh to Chicago, returning Sat, Sep 5, priced at $159 found 8 hours ago
Southwest Airlines
Wed, Oct 14 - Thu, Oct 15
PIT
Pittsburgh
MDW
Chicago
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Pittsburgh to Chicago, returning Thu, Oct 15, priced at $162 found 1 day ago
Delta
Tue, Sep 15 - Thu, Sep 17
PIT
Pittsburgh
MDW
Chicago
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 15 from Pittsburgh to Chicago, returning Thu, Sep 17, priced at $167 found 1 day ago
Southwest Airlines
Wed, Sep 2 - Sat, Sep 5
PIT
Pittsburgh
MDW
Chicago
$169 Roundtrip, found 8 hours ago
$169
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Pittsburgh to Chicago, returning Sat, Sep 5, priced at $169 found 8 hours ago
Southwest Airlines
Thu, Aug 13 - Mon, Aug 17
PIT
Pittsburgh
MDW
Chicago
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Aug 13 from Pittsburgh to Chicago, returning Mon, Aug 17, priced at $172 found 1 day ago
Southwest Airlines
Mon, Sep 7 - Fri, Sep 11
PIT
Pittsburgh
MDW
Chicago
$174 Roundtrip, found 10 hours ago
$174
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Mon, Sep 7 from Pittsburgh to Chicago, returning Fri, Sep 11, priced at $174 found 10 hours ago
Frontier Airlines
Thu, Dec 24 - Thu, Dec 31
PIT
Pittsburgh
MDW
Chicago
$849 Roundtrip, found 1 day ago
$849
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Dec 24 from Pittsburgh to Chicago, returning Thu, Dec 31, priced at $849 found 1 day ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $494
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $494

What you need to know for your flight from Pittsburgh Intl. to Midway Intl.

Pittsburgh (PIT) to Chicago (MDW) at a glance

Travel from Pittsburgh (PIT) to Chicago (MDW) with a selection of airlines operating this domestic short-haul route. Whether you're looking for affordable options or full-service flights, you can compare choices to discover the best itinerary that aligns with your budget and schedule. Explore the famous attractions and vibrant neighborhoods of Chicago as you plan your journey. Here you’ll find essential information about flights from Pittsburgh International Airport to Midway International Airport.

  • Fastest flight duration: around 1h 30m non-stop
  • Route distance: roughly 400 miles (645 km)
  • Flights per week: around 12 departures on average
  • Typical fares (one-way): economy tickets often range from $40–$360, depending on seasonality and how far ahead you book

Flights from Pittsburgh International Airport (PIT) to Midway International Airport (MDW)

Based on the latest traveler bookings, here are the top airlines flying from Pittsburgh to Chicago, favored for both non-stop and one-stop flights. Common layover choices include Philadelphia International Airport (PHL) with a layover of about 1 hour and 30 minutes, Detroit Metropolitan Wayne County Airport (DTW) with a 45-minute layover, and Hartsfield-Jackson Atlanta International Airport (ATL) offering a 1-hour layover. These options allow you to mix and match pricing, total travel time, and cabin class to find the perfect itinerary for your needs.

  • Southwest Airlines: This budget-friendly airline provides both non-stop and one-stop flights, with one-way ticket prices generally falling between $40 and $360. It dominates this route, making up about 95% of all departures, with a typical non-stop flight taking around 1 hour and 30 minutes.
  • Delta: Offering full-service travel, Delta features one-stop flights priced from $90 to $445 for one-way tickets. It accounts for roughly 3% of the departures on this route, with an in-flight duration of 3 hours and 15 minutes, resulting in a total journey time of about 5 hours when including the layover.
  • Frontier Airlines: As a low-cost option, Frontier provides one-stop services with one-way fares usually ranging from $70 to $145. This airline represents about 1% of the departures on this route, with an in-flight time of 3 hours and 15 minutes, leading to an overall travel time of approximately 5 hours, considering the layover.

Best time to fly from Pittsburgh (PIT) to Chicago (MDW)

The most popular months for travelers flying from Pittsburgh to Chicago are April, August, and October, when peak temperatures in Chicago reach up to 73°F in August. If you prefer quieter travel, consider January, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 25.7°F. For better deals, November usually offers the lowest average one-way fare around $131. Flight availability peaks in July and August, with approximately 15 flights per week, making it easier to find convenient departure times.

  • Cheapest time to fly: November usually offers good deals with average one-way fare around $131, roughly 23% cheaper than the yearly average.
  • More budget-friendly months to fly: August and December typically offer average one-way fares of around $134.
  • Most flight options: July and August have the highest number of flights from Pittsburgh to Chicago, with approximately 15 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January25.7°F (-3.5°C)Low9$183
February27.0°F (-2.8°C)Low9$196
March37.0°F (2.8°C)Average10$213
April46.0°F (7.8°C)High11$205
May57.0°F (13.9°C)Low10$194
June67.3°F (19.6°C)Average12$172
July73.4°F (23.0°C)Average15$193
August73.0°F (22.8°C)High15$133
September67.1°F (19.5°C)Average13$156
October54.9°F (12.7°C)High14$146
November42.3°F (5.7°C)Average12$131
December33.1°F (0.6°C)Average11$136

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Pittsburgh (PIT) to Chicago (MDW)

  • Pittsburgh to Chicago (PIT-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). On this route, one-way economy fares generally fall between $45 and $335, influenced by the season and how far in advance you book. Travelers can choose from both non-stop and one-stop flights. Major airlines operating this route include United and American Airlines, with first-class service also offered.

How to find the best prices for flights from Pittsburgh (PIT) to Chicago (MDW)

Getting some of the best deals on flights from Pittsburgh to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking 2-8 weeks in advance, which coincides with when most travelers make their reservations. Afternoon departures, between 12 PM and 6 PM, not only tend to be less expensive but are also the most sought-after flight times. Additionally, flying on Tuesday typically offers lower prices, while Friday remains the most popular travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Midway International Airport from Pittsburgh International Airport

Chicago welcomes travelers from Pittsburgh with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Midway International Airport, travelers can easily access several transport options. Midway Station, a metro station, is located about 0.2 miles away on foot, while Chicago Ashburn Station, a train station, is approximately 4.1 miles away by car. Additionally, Lyons Seaport, a seaport, is situated around 7.2 miles from the airport, also accessible by car.

Frequently asked questions

How much does a flight from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $69 and cheap return flights from $137 Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $147 and $486, and return flights often range between $243 and $819. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from PIT to MDW is August when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter PIT to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines is one of the cheapest airlines offering nonstop flights from Pittsburgh, PA (PIT) to Chicago, IL (MDW), with round-trip tickets starting from around $431. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Pittsburgh, PA (PIT) to Chicago, IL (MDW) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN offers the most daily flights from Pittsburgh to Chicago, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
On average, there are around 3 nonstop flights per day from Pittsburgh Intl. (PIT) to Midway Intl. (MDW). For more options, look at flights that include layovers.
What is the earliest flight from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Pittsburgh International Airport (PIT) to Midway International (MDW) usually departs at around 5:00 AM, operated by Southwest Airlines. This seasonal service is available in January and December, making it perfect for early risers looking to start their day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
For flights from Pittsburgh, PA (PIT) to Chicago, IL (MDW), the most popular departure times are in the early afternoon, from 12pm to 3pm. About 26% of passengers prefer this time window. Many major carriers, including Southwest Airlines, offer flights during this window. This timing is popular because it allows travelers to enjoy their morning before heading to the airport.
How long does it take to fly from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from PIT to MDW typically takes around 1 hour 30 minutes, covering approximately 399 miles. Connecting flights on this route usually add 5 hours 30 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the PIT to MDW route with Delta Air Lines.
How do I earn miles on a Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Pittsburgh Intl. (PIT)?
When traveling from Pittsburgh Intl. (PIT) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), LaGuardia (LGA), Ronald Reagan Washington National (DCA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

0
Origin airport
Pittsburgh Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$137
Distance
399 mi

Book with confidence

Pittsburgh to Chicago Flights

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

 

The best time to book a flight from Pittsburgh to Chicago

Sunday is one of the best days to book for cheap flights from Pittsburgh 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 Pittsburgh 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 Pittsburgh to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $69 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 Pittsburgh 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 Pittsburgh 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.

 

Pittsburgh to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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