Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Pittsburgh to Chicago from $79

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pittsburgh to Chicago departing on 4/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Pittsburgh to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:25 pm - 1:55 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
7:45 am - 10:05 am
MDW
-
PIT
1h 20mnonstop
$175Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
7:10 pm - 7:40 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
4:20 pm - 9:05 pm
MDW
-
PIT
3h 45m
1 stop
$185Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
12:30 pm - 7:45 pm
PIT
-
MDW
8h 15m
2 stops
Southwest Logo
4:00 pm - 6:20 pm
MDW
-
PIT
1h 20mnonstop
$190Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
8:00 pm - 8:30 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
7:40 am - 10:00 am
MDW
-
PIT
1h 20mnonstop
$193Southwest
Thu, May 7 - Mon, May 11
Delta Logo
10:20 am - 4:25 pm
PIT
-
MDW
7h 05m
1 stop
Delta Logo
6:38 pm - 10:56 pm
MDW
-
PIT
3h 18m
1 stop
$195Delta
Tue, Apr 21 - Mon, Apr 27
Southwest Logo
6:55 pm - 10:15 pm
PIT
-
MDW
4h 20m
1 stop
Southwest Logo
9:15 am - 9:05 pm
MDW
-
PIT
10h 50m
2 stops
$200Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
8:00 pm - 8:30 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
5:40 pm - 10:15 pm
MDW
-
PIT
3h 35m
1 stop
$203Southwest
Thu, May 7 - Mon, May 11
Southwest Logo
12:30 pm - 7:45 pm
PIT
-
MDW
8h 15m
2 stops
Southwest Logo
9:15 am - 9:05 pm
MDW
-
PIT
10h 50m
2 stops
$205Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
5:45 am - 1:05 pm
PIT
-
MDW
8h 20m
2 stops
Southwest Logo
6:55 pm - 9:20 pm
MDW
-
PIT
1h 25mnonstop
$208Southwest
Thu, May 7 - Mon, May 11
Southwest Logo
8:05 pm - 10:45 pm
PIT
-
MDW
3h 40m
1 stop
Southwest Logo
5:50 pm - 11:10 pm
MDW
-
PIT
4h 20m
1 stop
$213Southwest
Thu, Apr 16 - Mon, Apr 20

Southwest flights from Pittsburgh to Chicago Midway Airport

Our best Southwest deals on Pittsburgh to Chicago Midway Airport flight tickets
Southwest
Apr 22
PIT1:25 pmPittsburgh
1h 30m
MDW1:55 pmChicago Midway
Apr 25
MDW7:45 amChicago Midway
1h 20m
PIT10:05 amPittsburgh
$175
Southwest
Apr 22
PIT7:10 pmPittsburgh
1h 30m
MDW7:40 pmChicago Midway
Apr 25
MDW4:20 pmChicago Midway
3h 45m
1 stop
PIT9:05 pmPittsburgh
$185
Southwest
Apr 22
PIT12:30 pmPittsburgh
8h 15m
2 stops
MDW7:45 pmChicago Midway
Apr 25
MDW4:00 pmChicago Midway
1h 20m
PIT6:20 pmPittsburgh
$190

Delta flights from Pittsburgh to Chicago Midway Airport

Our best Delta deals on Pittsburgh to Chicago Midway Airport flight tickets
Delta
Apr 21
PIT11:55 amPittsburgh
5h 30m
1 stop
MDW4:25 pmChicago Midway
Apr 27
MDW5:21 pmChicago Midway
6h 10m
1 stop
PIT12:31 amPittsburgh
$195
Delta
Feb 28
PIT10:54 amPittsburgh
5h 27m
1 stop
MDW3:21 pmChicago Midway
Mar 2
MDW6:20 pmChicago Midway
3h 17m
1 stop
PIT10:37 pmPittsburgh
$213
Delta
Apr 10
PIT6:30 amPittsburgh
3h 23m
1 stop
MDW8:53 amChicago Midway
Apr 13
MDW5:21 pmChicago Midway
6h 10m
1 stop
PIT12:31 amPittsburgh
$278

momondo Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 6, 2026.
Use the filters below to find and compare flights from Pittsburgh to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/22

1:25 pm-1:55 pm

Nonstop1h 30m

Chicago Midway

Sat 4/25

7:45 am-10:05 am

Nonstop1h 20m

$175

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/22

7:10 pm-7:40 pm

Nonstop1h 30m

Chicago Midway

Sat 4/25

4:20 pm-9:05 pm

1 stop3h 45m

$185

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/22

12:30 pm-7:45 pm

2 stops8h 15m

Chicago Midway

Sat 4/25

4:00 pm-6:20 pm

Nonstop1h 20m

$190

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 5/7

8:00 pm-8:30 pm

Nonstop1h 30m

Chicago Midway

Mon 5/11

7:40 am-10:00 am

Nonstop1h 20m

$193

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 4/21

10:20 am-4:25 pm

1 stop7h 05m

Chicago Midway

Mon 4/27

6:38 pm-10:56 pm

1 stop3h 18m

$195

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/22

6:55 pm-10:15 pm

1 stop4h 20m

Chicago Midway

Sat 4/25

9:15 am-9:05 pm

2 stops10h 50m

$200

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 5/7

8:00 pm-8:30 pm

Nonstop1h 30m

Chicago Midway

Mon 5/11

5:40 pm-10:15 pm

1 stop3h 35m

$203

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 4/22

12:30 pm-7:45 pm

2 stops8h 15m

Chicago Midway

Sat 4/25

9:15 am-9:05 pm

2 stops10h 50m

$205

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 5/7

5:45 am-1:05 pm

2 stops8h 20m

Chicago Midway

Mon 5/11

6:55 pm-9:20 pm

Nonstop1h 25m

$208

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 4/16

8:05 pm-10:45 pm

1 stop3h 40m

Chicago Midway

Mon 4/20

5:50 pm-11:10 pm

1 stop4h 20m

$213

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Pittsburgh to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Pittsburgh, with most prices found around $201. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Pittsburgh during the month October is also very affordable. Most momondo users find prices during this month for around $248.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Pittsburgh. The lowest ticket price found for a Wednesday departure recently was $350. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Pittsburgh because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $416.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Pittsburgh at noon is the least expensive time of day to depart. momondo users have found prices as low as $335 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $389. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Pittsburgh to Chicago Midway flight route?

Fly from Pittsburgh to Chicago Midway for the best Pittsburgh - Chicago Midway flight prices

What cabin class options are available on Pittsburgh to Chicago Midway flights?

There is only 1 cabin class available to choose from on Pittsburgh to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Pittsburgh to Chicago Midway Airport flights?

You could potentially save up to 47% on your flight if you consider stops on a Pittsburgh to Chicago Midway Airport flight.

When to book flights from Pittsburgh to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Pittsburgh to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Pittsburgh to Chicago Midway Airport (PIT to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pittsburgh to Chicago Midway Airport

Best Price Found

$193

Fastest flight time

1h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Pittsburgh in the past 72 hours is $193. The best round-trip flight deal from Pittsburgh to Chicago Midway Airport found on momondo in the last 72 hours is $331.
The fastest flight from Pittsburgh to Chicago Midway Airport takes 1h 20m
Direct flights go from Pittsburgh to Chicago Midway Airport every day.
Search flight deals

  • How far is Pittsburgh to Chicago Midway by plane?

    The straight-line distance from Pittsburgh to Chicago Midway is 413.5 mi. 1h 20m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Pittsburgh Airport to Chicago Midway Airport?

    Prices for flights from Pittsburgh Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Pittsburgh Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Pittsburgh Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Pittsburgh Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Pittsburgh to Chicago Midway Airport?

  • What is the most popular airline from Pittsburgh to Chicago Midway Airport?

Best airlines flying from Pittsburgh to Chicago Midway Airport

Compare and see reviews for airlines that fly from Pittsburgh to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $97Free CancellationRating
8.0
4,280 reviews
Search Southwest flights

  • Southwest Flights From Pittsburgh to Chicago Midway Airport

    The lowest priced Southwest flight from Pittsburgh to Chicago Midway Airport from the last 72 hours was $97. Generally, Southwest has 17 flights on this route every week with an average price of $313. Southwest is rated 8.0/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Pittsburgh to Chicago?

It is quick and easy to find Pittsburgh to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Pittsburgh to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Pittsburgh to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Pittsburgh to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Pittsburgh.

I’m not ready to book a flight from Pittsburgh to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Pittsburgh and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 3/8
Sun 3/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago