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$99+ Cheap flights from Pittsburgh (PIT) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Pittsburgh to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

May

Cheapest in

March

Round-trip from

$153
(Southwest)

One-way from

$99
(Southwest)
Provider with most accurate pricing for Pittsburgh-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Pittsburgh-Chicago Midway flights.
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High demand for flights, 35% potential price rise
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Best time to find cheap flights, 36% potential price drop
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From Pittsburgh to Chicago Midway
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One-way flight from Pittsburgh to Chicago Midway
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Find flight deals from Pittsburgh to Midway

Cheapest flights from Pittsburgh to Midway
Explore the most affordable flight options available from Pittsburgh to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This Southwest deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/178:20 amPIT - MDW
Nonstop1h 35mSouthwest
Thu 12/198:20 amMDW - PIT
Nonstop1h 20mSouthwest
Deal found 11/19$153
This Delta deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/104:35 pmPIT - MDW
1 stop6h 31mDelta
Tue 12/175:50 pmMDW - PIT
1 stop4h 06mDelta
Deal found 11/18$176
This Mytrip deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/47:33 pmPIT - MDW
2 stops22h 07mMultiple Airlines
Thu 1/99:21 amMDW - PIT
1 stop10h 49mMultiple Airlines
Deal found 11/19$510

Find flights from Pittsburgh to Midway within your budget

Customize your flight search to find flights from Pittsburgh to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 12/17

8:20 am-8:55 am

Nonstop1h 35m

Chicago Midway

Thu 12/19

8:20 am-10:40 am

Nonstop1h 20m

$153

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 1/12

4:41 pm-12:13 am

1 stop8h 32m

Chicago Midway

Thu 1/16

7:15 am-3:44 pm

1 stop7h 29m

$157

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 12/10

4:35 pm-10:06 pm

1 stop6h 31m

Chicago Midway

Tue 12/17

5:50 pm-10:56 pm

1 stop4h 06m

$176

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 12/4

7:33 pm-4:40 pm

2 stops22h 07m

Chicago Midway

Thu 1/9

9:21 am-9:10 pm

1 stop10h 49m

$510

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 12/24

8:20 am-8:55 am

Nonstop1h 35m

$99

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 12/17

6:16 pm-10:06 pm

1 stop4h 50m

$129

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 1/2

9:56 pm-7:32 pm

1 stop22h 36m

$135

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 3/11

9:00 am-5:46 pm

1 stop9h 46m

$145

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 11/26

8:06 pm-5:26 pm

2 stops22h 20m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Compare providers for flights from Pittsburgh to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pittsburgh to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Pittsburgh-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pittsburgh-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pittsburgh-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Pittsburgh to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pittsburgh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Pittsburgh to Midway

Get recent, data-driven insights about flights from Pittsburgh to Midway including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Pittsburgh to Chicago Midway Airport?

Currently, December is the cheapest month in which you can book a flight from Pittsburgh to Chicago Midway Airport (average of $159). Flying from Pittsburgh to Chicago Midway Airport in July is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PIT to MDW?

Find hourly flight availability from Pittsburgh to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 17% on flights from Pittsburgh to Chicago Midway Airport by exploring options for tickets in the evening.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated November 20, 2024.
Read through reviews of airlines operating flights from Pittsburgh to Chicago, such as Delta and Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Allegiant Air
7.4
Good
850 reviews
Southwest
8.1
Very good
5,014 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,014 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Pittsburgh to Chicago Midway?

    For a flight from Pittsburgh to Chicago Midway, you will be flying from Pittsburgh. Pittsburgh (PIT) is just 13.5 mi from the center of the city. Pittsburgh is the only Pittsburgh airport and it handles 2 outbound flights to Chicago Midway per day. 2 airlines have flights to Chicago Midway from Pittsburgh on a regular basis.

  • What are the cheapest airlines flying from Pittsburgh to Chicago Midway Airport round-trip?

    Southwest, at $153, was found to be the cheapest airline from Pittsburgh to Chicago Midway Airport.Alternate airlines to your destination round-trip include Frontier and Delta. Southwest is priced at 48% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Pittsburgh to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $99. Delta flights start at $129 while deals on Frontier start at $135 one-way.

  • What are the cheapest flights from Pittsburgh to Chicago Midway Airport?

    On average you can expect to pay $349 for a flight from Pittsburgh to Chicago Midway Airport. The cheapest flight overall is $109 while the most popular route, (Pittsburgh - Chicago Midway) is currently priced at $153.

  • Can I find deals for flights from Pittsburgh to Midway that include hotel bookings?

    Yes. In addition to deals on Pittsburgh to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pittsburgh to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pittsburgh to Midway.

  • Can I find deals for business class flights from Pittsburgh to Midway?

    Yes. Cheapflights offers flight deals from Pittsburgh to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pittsburgh to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Pittsburgh to Chicago Midway Airport (average of $159). Flying from Pittsburgh to Chicago Midway Airport in July is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Pittsburgh to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Pittsburgh to Midway

Discover the top 2 airlines that operate flights from Pittsburgh to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$148Average$296FlexibilityNo cancel feeOn-time63%
DeltaCheapest$155Average$363FlexibilityNo cancel feeOn-timeN/A
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