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

View $69 flight on Wed, Aug 26, 2026Opens in a new window

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

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Cheap Flights from Chicago to Pittsburgh (MDW-PIT)

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
Mon, Sep 21 - Wed, Sep 23
MDW
Chicago
PIT
Pittsburgh
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Sep 21 from Chicago to Pittsburgh, returning Wed, Sep 23, priced at $137 just found
Southwest Airlines
Fri, Sep 11 - Mon, Sep 14
MDW
Chicago
PIT
Pittsburgh
$142 Roundtrip, just found
$142
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Sep 11 from Chicago to Pittsburgh, returning Mon, Sep 14, priced at $142 just found
Southwest Airlines
Mon, Sep 21 - Wed, Sep 23
MDW
Chicago
PIT
Pittsburgh
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Sep 21 from Chicago to Pittsburgh, returning Wed, Sep 23, priced at $147 just found
Southwest Airlines
Fri, Sep 11 - Mon, Sep 14
MDW
Chicago
PIT
Pittsburgh
$152 Roundtrip, just found
$152
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Sep 11 from Chicago to Pittsburgh, returning Mon, Sep 14, priced at $152 just found
Delta
Tue, Sep 15 - Wed, Sep 16
MDW
Chicago
PIT
Pittsburgh
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 15 from Chicago to Pittsburgh, returning Wed, Sep 16, priced at $157 found 1 day ago
Southwest Airlines
Fri, Sep 11 - Mon, Sep 14
MDW
Chicago
PIT
Pittsburgh
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Sep 11 from Chicago to Pittsburgh, returning Mon, Sep 14, priced at $157 just found
Southwest Airlines
Wed, Feb 10 - Wed, Feb 17
MDW
Chicago
PIT
Pittsburgh
$158 Roundtrip, found 8 hours ago
$158
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Feb 10 from Chicago to Pittsburgh, returning Wed, Feb 17, priced at $158 found 8 hours ago
Southwest Airlines
Fri, Sep 11 - Mon, Sep 14
MDW
Chicago
PIT
Pittsburgh
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Sep 11 from Chicago to Pittsburgh, returning Mon, Sep 14, priced at $162 just found
Southwest Airlines
Thu, Sep 17 - Mon, Sep 21
MDW
Chicago
PIT
Pittsburgh
$162 Roundtrip, found 5 hours ago
$162
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Thu, Sep 17 from Chicago to Pittsburgh, returning Mon, Sep 21, priced at $162 found 5 hours ago
Southwest Airlines
Mon, Sep 21 - Wed, Sep 23
MDW
Chicago
PIT
Pittsburgh
$164 Roundtrip, just found
$164
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Sep 21 from Chicago to Pittsburgh, returning Wed, Sep 23, priced at $164 just found

Alternative airports near Pittsburgh

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

Select flight to Pittsburgh Intl. PIT. Cheapest option available. Average driving time to city center is 24 minutes. Flights from $369
PIT
Pittsburgh Intl.
Cheapest
Average driving time to city center24 min
Flights from $369

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

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

Travel between Chicago (MDW) and Pittsburgh (PIT) with a range of airlines offering convenient routes on this domestic short-haul journey. Evaluate choices from both full-service and low-cost carriers to secure the best itinerary for your budget, schedule, and plans as you discover Pittsburgh's renowned attractions and vibrant neighborhoods. Here, you can find essential details about flights from Midway International Airport to Pittsburgh International Airport.

  • Fastest flight duration: around 1h 30m non-stop
  • Route distance: roughly 400 miles (645 km)
  • Flights per week: around 11 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 Midway International Airport (MDW) to Pittsburgh International Airport (PIT)

Based on the latest traveler bookings, here are the most popular airlines flying from Chicago to Pittsburgh, featuring both non-stop and one-stop options. Common layover points include Philadelphia International Airport (PHL) with around a 1-hour layover, Detroit Metropolitan Wayne County Airport (DTW) at approximately 50 minutes, and Orlando International Airport (MCO) with a layover of about 1 hour and 15 minutes. This variety allows you to balance ticket prices, total travel time, and cabin class to create the ideal travel itinerary.

  • 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, accounting for about 93% of all departures, and a typical non-stop flight lasts around 1 hour and 30 minutes.
  • Frontier Airlines: Another low-cost option, Frontier offers one-stop services with one-way fares typically ranging from $80 to $145. It makes up roughly 4% of the departures on this route, featuring an in-flight duration of 3 hours and 15 minutes, with a total travel time of about 4 hours and 15 minutes, including layover.
  • Delta: As a full-service airline, Delta provides one-stop services with one-way fares usually between $85 and $375. It represents approximately 4% of departures on this route, with an in-flight time of 3 hours and 15 minutes, leading to a total journey time of around 4 hours and 15 minutes, including layover.

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

The most popular months for travelers flying from Chicago to Pittsburgh are April, September, and October, when peak temperatures in Pittsburgh reach up to 66.2°F in September. If you prefer quieter travel, consider January, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 28.6°F. For better deals, September usually offers the lowest average one-way fare around $105. Flight availability peaks in September, with approximately 14 flights per week, making it easier to find convenient departure times. February has the fewest flights, with approximately 8 flights per week.

  • Cheapest time to fly: September usually offers good deals with average one-way fare around $105, roughly 35% cheaper than the yearly average.
  • Another budget-friendly time to fly: November typically offers an average one-way fare of around $119.
  • Most flight options: September has the highest number of flights from Chicago to Pittsburgh, with approximately 14 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January28.6°F (-1.9°C)Low10$168
February31.3°F (-0.4°C)Low8$232
March40.5°F (4.7°C)Average11$224
April51.1°F (10.6°C)High10$202
May61.7°F (16.5°C)Low9$185
June69.4°F (20.8°C)Average9$162
July73.9°F (23.3°C)Average10$163
August72.1°F (22.3°C)Average11$138
September66.2°F (19.0°C)High14$105
October54.7°F (12.6°C)High13$126
November42.6°F (5.9°C)Average12$119
December35.2°F (1.8°C)Average10$147

*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 Chicago (MDW) to Pittsburgh (PIT)

  • Chicago to Pittsburgh (ORD-PIT): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy ticket prices on this route generally range from $45 to $360, influenced by the season and how early you book. Travelers can choose between non-stop and one-stop flights. Major airlines operating on this route include American Airlines and United. Additionally, first class service is available for those seeking a more premium experience.

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

Getting some of the best deals on flights from Chicago to Pittsburgh 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 found when booking 2-8 weeks in advance, which aligns with when most travelers make their reservations. Morning departures between 5 am and 12 pm often offer lower prices and are popular among flyers. Additionally, flying on Tuesday generally provides better deals, while Sunday 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 Pittsburgh International Airport from Midway International Airport

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

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Pittsburgh, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Pittsburgh International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Pittsburgh 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.

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.) cost?
You can find cheap one-way flights from $69 and cheap return flights from $137 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.) with Expedia. One-way flights generally range between $116 and $492, and roundtrip flights usually range from $196 to $788. 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
The cheapest month to fly from MDW to PIT is September 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
Enter MDW to PIT and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
Southwest Airlines is one of the cheapest airlines offering nonstop flights from Chicago, IL (MDW) to Pittsburgh, PA (PIT), with prices starting from around $77. 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
The best airline to fly with from Chicago, IL (MDW) to Pittsburgh, PA (PIT) 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 also offers the most daily flights from MDW to PIT, 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
There are approximately 3 nonstop flights per day from Midway Intl. (MDW) to Pittsburgh Intl. (PIT). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
The earliest flight from Chicago, Illinois (MDW) to Pittsburgh, Pennsylvania (PIT) typically departs at around 5:00 AM, operated by Southwest Airlines. Catching this early flight means you can arrive in Pittsburgh with plenty of time to enjoy your day. 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
The most popular departure times for flights from Midway International Airport (MDW) to Pittsburgh International Airport (PIT) are in the late morning, from 9am to noon. About 34% of passengers prefer this time window. Many major carriers, including Southwest Airlines and Delta Air Lines, offer flights during this window. This timing works well because it lets you travel after the morning rush, making for a smoother airport experience.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
Flying nonstop from MDW to PIT takes around 1 hour 20 minutes, with the route covering approximately 399 miles. Flights with a layover typically take 4 hours 30 minutes longer than direct options. 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
First class seats are offered on the MDW to PIT route with Delta Air Lines.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh 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 Pittsburgh from Midway Intl. (MDW)?
If you're planning to travel to Pittsburgh from Midway Intl. (MDW), you can fly into Pittsburgh Intl. (PIT) Some flights may connect through major hubs like Detroit Metropolitan Wayne County (DTW), Norfolk Intl. (ORF), Bradley Intl. (BDL) before reaching Pittsburgh. 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.) Pittsburgh 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 Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh Intl.)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Pittsburgh, PA (PIT-Pittsburgh 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

Origin airport
Midway Intl.
Destination airport
Pittsburgh Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$137
Distance
399 mi
Average flight time
2 hours 26 mins

Book with confidence

Chicago to Pittsburgh Flights

The cheapest times to fly from Chicago to Pittsburgh

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

 

The best time to book a flight from Chicago to Pittsburgh

Sunday is one of the best days to book for cheap flights from Chicago to Pittsburgh: 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 Chicago to Pittsburgh

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 Chicago to Pittsburgh 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 Chicago to Pittsburgh 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 Chicago to Pittsburgh 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.

 

Chicago to Pittsburgh Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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