Skip to main content
Beginning of main content

PIT (Pittsburgh) to MDW (Chicago) Flights $161.6

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap PIT to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
30 Sep - 4 Oct

PIT

Pittsburgh

MDW

Chicago

$161.60

roundtrip

found 1 hour ago

20 Nov - 23 Nov

PIT

Pittsburgh

MDW

Chicago

$162.68

roundtrip

found 6 hours ago

23 Sep - 25 Sep

PIT

Pittsburgh

MDW

Chicago

$162.68

roundtrip

found 1 hour ago

27 Aug - 30 Aug

PIT

Pittsburgh

MDW

Chicago

$167.60

roundtrip

found 1 hour ago

27 Aug - 30 Aug

PIT

Pittsburgh

MDW

Chicago

$168.73

roundtrip

found 1 hour ago

29 Aug - 3 Sep

PIT

Pittsburgh

MDW

Chicago

$168.73

roundtrip

found 3 days ago

19 Aug - 22 Aug

PIT

Pittsburgh

MDW

Chicago

$168.73

roundtrip

found 1 day ago

19 Aug - 21 Aug

PIT

Pittsburgh

MDW

Chicago

$173.60

roundtrip

found 12 hours ago

19 Aug - 21 Aug

PIT

Pittsburgh

MDW

Chicago

$174.79

roundtrip

found 12 hours ago

22 Sep - 25 Sep

PIT

Pittsburgh

MDW

Chicago

$177.60

roundtrip

just found

Chicago

ORD-O'Hare Intl.

$144.40

Interesting Facts About Flights from Pittsburgh to Chicago (PIT to MDW)

Question : How long will the flight typically be from Pittsburgh International Airport (PIT) to Chicago Midway International Airport (MDW)?
Answer : When flying from PIT to MDW, it will take one hour and 36 minutes on average.

Question : How often is the Pittsburgh International Airport (PIT) to Chicago Midway International Airport (MDW) route delayed?
Answer : The Pittsburgh to Chicago route has an 83% on-time rate, ranking in the 65th percentile worldwide in getting their passengers to their destinations on schedule. If a flight is delayed, though, expect an average of less than half an hour added to your flight time.

Question : Is this route your best bet for getting to Chicago with minimal delays?
Answer : The best measurement of overall promptness combines both on-time percentage and total delay minutes. PIT to MDW currently has 3 stars out of 5, an average score at best.

Question : How long does it take to get from PIT to MDW?
Answer : Southwest Airlines currently holds the fastest travel time with one hour and 30 minutes. So, you would arrive in Chicago at 5:35 PM CDT if you left Pittsburgh at 5:05 PM EDT. Remember, there is a time change of one hour.

Question : Should you take that vacation to Chicago in the next 30 days?
Answer : Aug 8th has seen bookings (as of Jul 24th) as cheap as $174. That comes in 41% below the average price for this route. Saving now means you'll have more cash in your hand for the trip.

Question : From Pittsburgh to Chicago, which day of the week is going to have the most flight times?
Answer : Monday has the greatest variety of flight times for Pittsburgh to Chicago with six. Saturday currently offers the fewest number of flight times with only two options.

Question : When flying into Chicago, is Chicago Midway International Airport your cheapest option?
Answer : O'Hare International Airport (ORD) is just 16 miles away and on average, flights are 26% cheaper for the coming two months. Save a few bucks and put it towards your next trip.