PIT - MDW

$59 Find Cheap Flights from Pittsburgh to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pittsburgh to Midway departing on 12/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Pittsburgh to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Pittsburgh to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$122
Overall average: $236
Southwest
Mon 12/15Wed 12/17
PIT - MDW • 1 stop
Cheapest non-stop
$158
Typical prices: $206-$262
Southwest
Sat 12/6Mon 12/8
PIT - MDW • Non-stop
Our travelers' advice
AI-generated summary based on content written by travel experts
Arrive early at PIT due to construction delays.
Use the CTA Orange Line from MDW for quick downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $122 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 34% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Pittsburgh to Midway (PIT-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pittsburgh to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pittsburgh to Midway

Mon, Dec 15 - Wed, Dec 17
Southwest Logo
5:45 am - 10:10 amPIT-MDW
5h 25m1 stop
Southwest Logo
2:10 pm - 9:05 pmMDW-PIT
5h 55m2 stops
$122Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
1:20 pm - 8:15 pmPIT-MDW
7h 55m2 stops
Southwest Logo
2:30 pm - 9:55 pmMDW-PIT
6h 25m2 stops
$127Southwest
Find Deal
Thu, Jan 15 - Mon, Jan 19
Delta Logo
6:00 am - 8:54 amPIT-MDW
3h 54m1 stop
Delta Logo
6:35 pm - 10:39 pmMDW-PIT
3h 04m1 stop
$157Delta
Find Deal
Sat, Dec 6 - Mon, Dec 8
Southwest Logo
6:05 pm - 6:35 pmPIT-MDW
1h 30mnonstop
Southwest Logo
10:15 am - 12:45 pmMDW-PIT
1h 30mnonstop
$158Southwest
Find Deal
Sat, Dec 6 - Mon, Dec 8
Southwest Logo
9:45 am - 2:05 pmPIT-MDW
5h 20m1 stop
Southwest Logo
10:15 am - 12:45 pmMDW-PIT
1h 30mnonstop
$168Southwest
Find Deal
Mon, Nov 24 - Thu, Nov 27
Delta Logo
6:00 am - 1:07 pmPIT-MDW
8h 07m1 stop
Delta Logo
5:34 pm - 12:21 amMDW-PIT
5h 47m1 stop
$177Delta
Find Deal
Fri, Nov 21 - Sun, Nov 23
Frontier Logo
11:04 am - 11:29 pmPIT-MDW
13h 25m1 stop
Frontier Logo
5:30 pm - 10:09 amMDW-PIT
15h 39m1 stop
$189Frontier
Find Deal
Sat, Nov 22 - Mon, Nov 24
Multiple Airlines Logo
8:38 pm - 11:42 amPIT-MDW
16h 04m1 stop
Multiple Airlines Logo
5:47 pm - 8:19 amMDW-PIT
13h 32m1 stop
$197Multiple Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
Multiple Airlines Logo
11:04 am - 11:29 pmPIT-MDW
13h 25m1 stop
Multiple Airlines Logo
6:20 am - 7:21 amMDW-PIT
24h 01m1 stop
$200Multiple Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 16
Frontier Logo
6:36 pm - 10:26 amPIT-MDW
16h 50m1 stop
Frontier Logo
8:32 am - 1:53 pmMDW-PIT
4h 21m1 stop
$208Frontier
Find Deal
Booking Insights

KAYAK's insights & trends for Pittsburgh to Midway flights

Get data-powered insights and trends into flights from Pittsburgh to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Pittsburgh to Chicago Midway Airport?

The average price of all round-trip flights from Pittsburgh to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Pittsburgh to Chicago Midway Airport, look for departures on Tuesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Thursday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Pittsburgh to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pittsburgh to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Pittsburgh to Chicago Midway Airport is September, where tickets cost $201 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is $435 and $372 respectively.

Can I save money by flying with a layover from Pittsburgh to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $304 on average.

Expert advice

Expert advice for your flight from Pittsburgh to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
PIT

Arrive early at PIT due to ongoing construction and potentially busy security lines, especially for morning flights.

Read more about PITby Matt Meltzer
MDW

Use the CTA Orange Line from MDW for a quick, 25-30 minute ride to downtown Chicago, avoiding traffic delays.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Matt Meltzer

Matt Meltzer

Expert on PIT

Matt Meltzer

Matt Meltzer

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Good to know

Low seasonJuly
Cheapest flight$59
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 34% lower on average.
Flight from Pittsburgh to Chicago Midway Airport

When to book flights from Pittsburgh to Midway

Are your dates flexible? Find out the best times to travel from Pittsburgh to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Pittsburgh to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Pittsburgh to Chicago Midway Airport was $59 for a one-way ticket and $122 for a round-trip.

  • Do I need a passport to fly between Pittsburgh and Chicago Midway Airport?

    No, a passport isn't needed to fly from Pittsburgh to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Pittsburgh to Chicago Midway Airport?

    On your way to Chicago Midway Airport, you’ll fly out from Pittsburgh. You’ll be landing at Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Pittsburgh to Chicago Midway Airport?

    American Airlines, Delta, Alaska Airlines, and JetBlue offer inflight Wi-Fi service on the Pittsburgh to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Pittsburgh to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Pittsburgh to Chicago Midway Airport flight route.

  • On which days can I fly direct from Pittsburgh to Chicago Midway Airport?

    There are nonstop flights from Pittsburgh to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Pittsburgh to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Pittsburgh to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pittsburgh to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Pittsburgh is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Pittsburgh to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Pittsburgh with another airline. Booking your flights between Pittsburgh and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pittsburgh to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Pittsburgh up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Pittsburgh to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $217 or less one-way and $289 or less round-trip.

Prefer to fly direct from Pittsburgh to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Pittsburgh to Chicago Midway.
Find which airlines fly direct from Pittsburgh Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Pittsburgh to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Pittsburgh

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Pittsburgh to Midway

 
See real verified KAYAK customer reviews for airlines flying from Pittsburgh to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Pittsburgh to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4241 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Everything you need to know for your flight from Pittsburgh to Midway

Information on your arrival and departure airports

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