PIT - MDW

$66 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 5/16. 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
$167
Overall average: $328
Southwest
czw. 4/9pon. 4/13
PIT - MDW • Non-stop
Cheapest non-stop
$197
Typical prices: $261-$493
Southwest
pon. 5/4czw. 5/7
PIT - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
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 $167 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 30m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 87% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Orlando (MCO)
Cheapest • Avg $200 (round-trip)
Detroit (DTW)
Shortest trip • 3h 23m (one-way)
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 38% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

czw., kwi 9 - pon., kwi 13
Southwest Logo
8:00 pm - 8:30 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
3:50 pm - 10:15 pm
MDW
-
PIT
5h 25m
1 stop
$167Southwest
czw., kwi 9 - pon., kwi 13
Southwest Logo
1:35 pm - 2:05 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
2:10 pm - 11:10 pm
MDW
-
PIT
8h 00m
2 stops
$172Southwest
czw., kwi 9 - pon., kwi 13
Delta Logo
12:22 pm - 6:40 pm
PIT
-
MDW
7h 18m
1 stop
Delta Logo
6:38 pm - 10:56 pm
MDW
-
PIT
3h 18m
1 stop
$177Delta
pon., kwi 6 - czw., kwi 9
Southwest Logo
8:05 pm - 11:00 pm
PIT
-
MDW
3h 55m
1 stop
Southwest Logo
2:10 pm - 11:10 pm
MDW
-
PIT
8h 00m
2 stops
$182Southwest
sob., kwi 11 - sob., kwi 11
Southwest Logo
10:05 am - 1:10 pm
PIT
-
MDW
4h 05m
1 stop
Southwest Logo
4:00 pm - 6:20 pm
MDW
-
PIT
1h 20mnonstop
$183Southwest
wt., mar 31 - sob., kwi 4
Delta Logo
10:26 am - 12:29 pm
PIT
-
MDW
3h 03m
1 stop
Delta Logo
9:35 am - 1:27 pm
MDW
-
PIT
2h 52m
1 stop
$187Delta
czw., maj 7 - pon., maj 11
Southwest Logo
5:45 am - 1:10 pm
PIT
-
MDW
8h 25m
2 stops
Southwest Logo
7:50 am - 12:55 pm
MDW
-
PIT
4h 05m
1 stop
$192Southwest
pon., maj 4 - czw., maj 7
Southwest Logo
8:00 pm - 8:30 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
7:40 am - 10:00 am
MDW
-
PIT
1h 20mnonstop
$197Southwest
śr., kwi 8 - sob., kwi 11
Southwest Logo
10:50 am - 5:05 pm
PIT
-
MDW
7h 15m
2 stops
Southwest Logo
7:25 am - 5:05 pm
MDW
-
PIT
8h 40m
1 stop
$212Southwest
pon., kwi 13 - czw., kwi 16
Southwest Logo
1:35 pm - 2:05 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
6:55 pm - 9:20 pm
MDW
-
PIT
1h 25mnonstop
$217Southwest
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 Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Thursday is the cheapest day to fly and Saturday 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 February, where the average cost of round-trip tickets is $546 and $477 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.

Find deals
Expert advice

Expert advice for your flight from Pittsburgh to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

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 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 seasonJanuary
Cheapest flight$66
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 39% 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 $66 for a one-way ticket and $167 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, JetBlue, Delta, and Alaska Airlines 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 $189 or less one-way and $325 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 4319 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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

Information on your arrival and departure airports

Pittsburgh (PIT)
Midway (MDW)