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

Compare Pittsburgh International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Pittsburgh International to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Pittsburgh International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $196. Find the lowest prices on one-way and return tickets right here.
Chicago.$196 per passenger.Departing Sat, 8 Aug, returning Wed, 12 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Sat, 8 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 12 Aug, arriving in Pittsburgh International.Price includes taxes and charges.From $196, select.
Chicago.$196 per passenger.Departing Wed, 21 Oct, returning Sat, 24 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Wed, 21 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 24 Oct, arriving in Pittsburgh International.Price includes taxes and charges.From $196, select.
Chicago.$196 per passenger.Departing Sat, 29 Aug, returning Sat, 5 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Sat, 29 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 5 Sep, arriving in Pittsburgh International.Price includes taxes and charges.From $196, select.
Chicago.$196 per passenger.Departing Mon, 21 Sep, returning Wed, 23 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Mon, 21 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 23 Sep, arriving in Pittsburgh International.Price includes taxes and charges.From $196, select.
Chicago.$259 per passenger.Departing Thu, 29 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Thu, 29 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in Pittsburgh International.Price includes taxes and charges.From $259, select.
Chicago.$259 per passenger.Departing Mon, 9 Nov, returning Tue, 10 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Mon, 9 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 10 Nov, arriving in Pittsburgh International.Price includes taxes and charges.From $259, select.
Chicago.$311 per passenger.Departing Sat, 26 Sep, returning Sat, 3 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Sat, 26 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in Pittsburgh International.Price includes taxes and charges.From $311, select.
Chicago.$344 per passenger.Departing Wed, 16 Dec, returning Mon, 21 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Wed, 16 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 21 Dec, arriving in Pittsburgh International.Price includes taxes and charges.From $344, select.
Chicago.$371 per passenger.Departing Sat, 27 Feb, returning Tue, 2 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Pittsburgh International on Sat, 27 Feb, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 2 Mar, arriving in Pittsburgh International.Price includes taxes and charges.From $371, select.
Chicago.$419 per passenger.Departing Sun, 3 Jan, returning Tue, 5 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pittsburgh International on Sun, 3 Jan, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 5 Jan, arriving in Pittsburgh International.Price includes taxes and charges.From $419, select.
Chicago.$449 per passenger.Departing Tue, 28 Jul, returning Tue, 4 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Tue, 28 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 4 Aug, arriving in Pittsburgh International.Price includes taxes and charges.From $449, select.
Chicago.$491 per passenger.Departing Sat, 27 Feb, returning Tue, 2 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Sat, 27 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Mar, arriving in Pittsburgh International.Price includes taxes and charges.From $491, select.
Chicago.$491 per passenger.Departing Tue, 5 Jan, returning Tue, 12 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Tue, 5 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 12 Jan, arriving in Pittsburgh International.Price includes taxes and charges.From $491, select.
Chicago.$491 per passenger.Departing Fri, 19 Feb, returning Mon, 22 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Fri, 19 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 22 Feb, arriving in Pittsburgh International.Price includes taxes and charges.From $491, select.
Chicago.$519 per passenger.Departing Sat, 26 Dec, returning Sat, 2 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Pittsburgh International on Sat, 26 Dec, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 2 Jan, arriving in Pittsburgh International.Price includes taxes and charges.From $519, select.
Chicago.$519 per passenger.Departing Sat, 26 Dec, returning Sat, 2 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Sat, 26 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 2 Jan, arriving in Pittsburgh International.Price includes taxes and charges.From $519, select.

Find the cheapest month to fly from Pittsburgh International to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Pittsburgh International to Chicago Midway flights are currently cheapest in August.
Jul
from $700
Aug
from $196
Sep
from $196
Oct
from $196
Nov
from $259
Dec
from $344
Jan
from $419
Feb
from $491
Mar
from $573
Apr
Find prices
May
from $589
Jun
Find prices

Direct flights from Pittsburgh International to Chicago Midway

Pittsburgh International to Chicago Midway: Alternative routes

Compare routes from Pittsburgh International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
ClosestCheapest
from $196
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Chicago O'Hare International

25km from central Chicago
Cheapest
from $196
Search flights

Chicago Rockford

127km from central Chicago
from $375
Search flights

Pittsburgh to Chicago: Flight information

The things to know before you go.
Cheapest flight found$196
Cheapest month to flyAugust
Average flight time1 hr, 31 mins
Most popular airlineSouthwest Airlines
Average flights per week25

Finding cheap flights from Pittsburgh International to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Pittsburgh International to Chicago Midway is $196. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 31 minutes is the average flight time from Pittsburgh International to Chicago Midway.
Southwest Airlines flies direct from Pittsburgh International to Chicago Midway.
As of July 2026, there are 25 flights per week flying from Pittsburgh International to Chicago Midway.
The cheapest month to fly from Pittsburgh International to Chicago Midway is usually August.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Pittsburgh International Airport to Chicago Midway Airport on Saturday, 29 August 2026.
Yes – the average flight time is 1 hour and 31 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Pittsburgh International Airport (PIT) to Chicago Midway Airport (MDW): what you need to know

  • Take a direct flight from Pittsburgh International Airport to Chicago Midway Airport and you'll be travelling for an average of 1 hour 25 minutes.

  • Chicago is one hour behind Pittsburgh and observes the UTC-6 timezone.

  • Take your pick of 12 weekly Pittsburgh International Airport to Chicago Midway Airport flights. The 06:20 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the last service of the day at 21:30.

  • Arrive at the airport on time so you don't miss your PIT to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid a last-minute sprint to the gate.

  • During popular months such as July, you'll want to get to the airport well in advance. Plan to arrive two hours before domestic departures and four hours ahead for international flights whenever you're travelling during a peak period in general.

  • Travelling to Chicago (and then exploring more of the United States!) is a breeze with Southwest Airlines. This popular carrier has direct flights from Pittsburgh International Airport to Chicago Midway Airport.

  • The airline that serves the most passengers on this route is Southwest Airlines.

  • With 77.34% of its services landing on schedule, Southwest Airlines is the most punctual carrier offering PIT to MDW flights.

  • Consider adding a stopover when booking your ticket from Pittsburgh International Airport to Chicago Midway Airport. Just uncheck 'Direct flights only' to break up your journey, or maybe even explore a new city along the way. Here are some options between PIT and MDW:

    • Detroit Wayne County Airport

    • Baltimore Washington International Airport

    • Raleigh / Durham Airport

Handy information about Pittsburgh International Airport (PIT)

  • You'll find PIT at 1000 Airport Boulevard.

  • Of all flights departing from Pittsburgh International Airport, 77% land on schedule at their destination.

  • Central Pittsburgh to Pittsburgh International Airport is approximately 32 kilometres. Depending on traffic, it'll take you about 30 minutes to get there if you're driving, ride-sharing or catching a taxi.

  • Expect a journey time of about 45 minutes on public transport.

  • Booked an early flight from Pittsburgh International Airport to Chicago Midway Airport? Avoid the last-minute rush to the terminal (and enjoy a little extra shut-eye) by picking one of these hotels near PIT:

Arriving at Chicago Midway Airport (MDW)

  • If you're landing on a late Pittsburgh International Airport to Chicago Midway Airport flight, nothing beats the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and resting not long after at one of these accommodation options near MDW:

  • Pick up a Chicago Midway Airport rental car and explore Chicago and beyond with your own wheels. Dollar, Hertz and Budget are leading providers you can book with here.

  • To get the lowest price, reserve your vehicle from Chicago Midway Airport around four weeks ahead.

Getting from Chicago Midway Airport (MDW) to central Chicago

  • You'll find MDW at 5700 South Cicero.

  • From Chicago Midway Airport, Chicago is approximately 16 kilometres away. It takes around 25 minutes to get to the centre driving.

  • It takes roughly 30 minutes if you're using public transport.

When to fly to Chicago Midway Airport (MDW)

  • The quietest month for a flight from Pittsburgh International Airport to Chicago Midway Airport is December, while July is the busiest. Choose the best time to go to Chicago based on whether you prefer a laid-back vibe or a more bustling atmosphere.

  • Lock in your flight from Pittsburgh International Airport to Chicago Midway Airport for July if you want to visit Chicago during its warmest month. Expect temperatures of between 16ºC (61ºF) and 28ºC (82ºF).

  • Search for cheap tickets from PIT to MDW in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of the United States

  • You've done Chicago, now it's time to discover more of the United States. Travel about 451 kilometres south-east to Columbus to check off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, you'll have a full itinerary ahead.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in the United States. Experience the best of this destination with a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Plan smart, explore more

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Prices shown on this page are estimated lowest prices only. Found in the last 12 days.