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Cheap flights from Pittsburgh to Chicago Midway Airport from $55

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 Midway Airport departing on 4/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Pittsburgh to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Pittsburgh to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Pittsburgh to Chicago.

Cheap last minute flights

Planning a quick getaway from Pittsburgh to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Pittsburgh to Chicago

Find recent round-trip train or bus tickets from Pittsburgh to Chicago.

All round-trip flight deals from Pittsburgh to Chicago

The cheapest plane tickets from Pittsburgh to Chicago found on KAYAK recently.
2:20 pm - 7:51 pmPIT-MDW
6h 31m1 stop
4:40 pm - 10:48 amMDW-PIT
17h 08m1 stop
$120Frontier
Find Deal
Tue, Apr 8 - Tue, Apr 15
6:05 am - 11:59 amPIT-MDW
6h 54m1 stop
6:28 pm - 10:40 pmMDW-PIT
3h 12m1 stop
$177Delta
Find Deal
Tue, Feb 18 - Tue, Feb 25
6:15 am - 6:55 amPIT-MDW
1h 40mnonstop
8:25 pm - 10:50 pmMDW-PIT
1h 25mnonstop
$201Southwest
Find Deal
Sat, Feb 15 - Mon, Feb 17
7:45 am - 4:30 pmPIT-MDW
9h 45m1 stop
8:25 pm - 10:50 pmMDW-PIT
1h 25mnonstop
$211Southwest
Find Deal
Sat, Feb 15 - Mon, Feb 17
1:50 pm - 2:20 pmPIT-MDW
1h 30mnonstop
10:15 am - 12:35 pmMDW-PIT
1h 20mnonstop
$217Southwest
Find Deal
Tue, Feb 18 - Tue, Feb 25
4:45 pm - 10:00 pmPIT-MDW
6h 15m1 stop
5:10 pm - 7:30 pmMDW-PIT
1h 20mnonstop
$227Southwest
Find Deal
Tue, Feb 18 - Tue, Feb 25
6:27 am - 12:42 pmPIT-MDW
7h 15m1 stop
9:33 am - 1:25 pmMDW-PIT
2h 52m1 stop
$237Delta
Find Deal
Tue, Feb 18 - Tue, Feb 25
9:05 pm - 9:40 pmPIT-MDW
1h 35mnonstop
8:40 am - 11:05 amMDW-PIT
1h 25mnonstop
$249Southwest
Find Deal
Sun, Feb 16 - Tue, Feb 18
4:41 pm - 12:17 amPIT-MDW
8h 36m1 stop
7:15 am - 3:44 pmMDW-PIT
7h 29m1 stop
$250Frontier
Find Deal
Sun, Feb 2 - Sun, Feb 9
4:25 pm - 12:15 amPIT-MDW
8h 50m1 stop
8:40 am - 11:05 amMDW-PIT
1h 25mnonstop
$259Southwest
Find Deal
Sun, Feb 16 - Tue, Feb 18
2:20 pm - 7:51 pmPIT-MDW
6h 31m1 stop
$55Frontier
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Tue, Apr 8
12:19 pm - 12:21 amPIT-MDW
13h 02m1 stop
$61Frontier
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Thu, Apr 10
12:50 pm - 1:20 pmPIT-MDW
1h 30mnonstop
$69Southwest
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Tue, Mar 4
4:45 pm - 10:00 pmPIT-MDW
6h 15m1 stop
$79Southwest
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Thu, Feb 20
4:55 pm - 10:29 pmPIT-MDW
6h 34m1 stop
$89Delta
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Wed, Apr 30
10:28 am - 1:05 pmPIT-MDW
3h 37m1 stop
$119Delta
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Mon, Feb 17
9:00 am - 5:46 pmPIT-MDW
9h 46m1 stop
$136Allegiant Air
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Tue, Mar 11
9:00 am - 5:46 pmPIT-MDW
9h 46m1 stop
$141Allegiant Air
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Tue, Mar 18
6:14 pm - 5:36 pmPIT-MDW
24h 22m3 stops
Wed, Mar 5
6:14 pm - 5:36 pmPIT-MDW
24h 22m3 stops
Wed, Mar 12
7:15 pm - 7:45 pmPIT-MDW
1h 30mnonstop
1:45 pm - 4:05 pmMDW-PIT
1h 20mnonstop
$617Southwest
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Fri, Jan 24 - Mon, Jan 27
6:15 am - 12:30 pmPIT-MDW
7h 15m1 stop
5:10 pm - 7:30 pmMDW-PIT
1h 20mnonstop
$627Southwest
Find Deal
Fri, Jan 24 - Mon, Jan 27
12:00 pm - 4:50 pmPIT-MDW
5h 50m2 stops
1:45 pm - 4:05 pmMDW-PIT
1h 20mnonstop
$632Southwest
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Fri, Jan 24 - Mon, Jan 27
12:50 pm - 1:20 pmPIT-MDW
1h 30mnonstop
5:10 pm - 7:30 pmMDW-PIT
1h 20mnonstop
$668Southwest
Find Deal
Wed, Jan 22 - Wed, Jan 22
7:15 pm - 7:45 pmPIT-MDW
1h 30mnonstop
5:00 pm - 7:20 pmMDW-PIT
1h 20mnonstop
$673Southwest
Find Deal
Fri, Jan 24 - Sat, Jan 25
6:00 am - 11:45 amPIT-MDW
6h 45m1 stop
1:45 pm - 4:05 pmMDW-PIT
1h 20mnonstop
$678Southwest
Find Deal
Wed, Jan 22 - Wed, Jan 22
1:15 pm - 10:05 pmPIT-MDW
9h 50m1 stop
1:05 pm - 3:25 pmMDW-PIT
1h 20mnonstop
$683Southwest
Find Deal
Fri, Jan 24 - Sun, Jan 26
7:15 pm - 7:45 pmPIT-MDW
1h 30mnonstop
1:20 pm - 10:30 pmMDW-PIT
8h 10m2 stops
$688Southwest
Find Deal
Fri, Jan 24 - Sun, Jan 26
6:00 am - 11:45 amPIT-MDW
6h 45m1 stop
2:25 pm - 10:00 pmMDW-PIT
6h 35m2 stops
$692Southwest
Find Deal
Wed, Jan 22 - Wed, Jan 22
6:15 am - 6:55 amPIT-MDW
1h 40mnonstop
8:25 pm - 10:50 pmMDW-PIT
1h 25mnonstop
$201Southwest
Find Deal
Sat, Feb 15 - Mon, Feb 17
1:50 pm - 2:20 pmPIT-MDW
1h 30mnonstop
10:15 am - 12:35 pmMDW-PIT
1h 20mnonstop
$217Southwest
Find Deal
Tue, Feb 18 - Tue, Feb 25
9:05 pm - 9:40 pmPIT-MDW
1h 35mnonstop
8:40 am - 11:05 amMDW-PIT
1h 25mnonstop
$249Southwest
Find Deal
Sun, Feb 16 - Tue, Feb 18
6:15 am - 6:55 amPIT-MDW
1h 40mnonstop
8:25 pm - 10:50 pmMDW-PIT
1h 25mnonstop
$295Southwest
Find Deal
Sat, Feb 22 - Sun, Feb 23
7:50 pm - 8:20 pmPIT-MDW
1h 30mnonstop
8:25 pm - 10:50 pmMDW-PIT
1h 25mnonstop
$313Southwest
Find Deal
Sat, Feb 15 - Sun, Feb 16
6:45 am - 7:15 amPIT-MDW
1h 30mnonstop
9:30 pm - 11:50 pmMDW-PIT
1h 20mnonstop
$325Southwest
Find Deal
Thu, Mar 20 - Sat, Mar 22
7:30 pm - 8:00 pmPIT-MDW
1h 30mnonstop
3:20 pm - 5:40 pmMDW-PIT
1h 20mnonstop
$343Southwest
Find Deal
Fri, Apr 11 - Sun, Apr 13
12:25 pm - 12:55 pmPIT-MDW
1h 30mnonstop
10:30 pm - 12:50 amMDW-PIT
1h 20mnonstop
$345Southwest
Find Deal
Thu, Mar 13 - Sun, Mar 23
9:05 pm - 9:40 pmPIT-MDW
1h 35mnonstop
8:10 am - 10:35 amMDW-PIT
1h 25mnonstop
$361Southwest
Find Deal
Fri, Feb 14 - Sun, Feb 16
8:30 pm - 9:00 pmPIT-MDW
1h 30mnonstop
7:50 am - 10:15 amMDW-PIT
1h 25mnonstop
$365Southwest
Find Deal
Fri, Jun 20 - Mon, Jun 23

Frontier flights from Pittsburgh to Chicago Midway Airport

Our best Frontier deals on Pittsburgh to Chicago Midway Airport flight tickets
Frontier
Apr 8
PIT2:20 pmPittsburgh
6h 31m
1 stop
MDW7:51 pmChicago Midway
Apr 15
MDW4:40 pmChicago Midway
17h 08m
1 stop
PIT10:48 amPittsburgh
Frontier
Feb 2
PIT4:41 pmPittsburgh
8h 36m
1 stop
MDW12:17 amChicago Midway
Feb 9
MDW7:15 amChicago Midway
7h 29m
1 stop
PIT3:44 pmPittsburgh
Frontier
Jan 30
PIT4:41 pmPittsburgh
8h 36m
1 stop
MDW12:17 amChicago Midway
Feb 2
MDW7:15 amChicago Midway
7h 29m
1 stop
PIT3:44 pmPittsburgh

Delta flights from Pittsburgh to Chicago Midway Airport

Our best Delta deals on Pittsburgh to Chicago Midway Airport flight tickets
Delta
Feb 18
PIT6:05 amPittsburgh
6h 54m
1 stop
MDW11:59 amChicago Midway
Feb 25
MDW6:28 pmChicago Midway
3h 12m
1 stop
PIT10:40 pmPittsburgh
Delta
Feb 18
PIT6:27 amPittsburgh
7h 15m
1 stop
MDW12:42 pmChicago Midway
Feb 25
MDW9:33 amChicago Midway
2h 52m
1 stop
PIT1:25 pmPittsburgh
Delta
Feb 23
PIT10:28 amPittsburgh
3h 37m
1 stop
MDW1:05 pmChicago Midway
Feb 26
MDW5:05 pmChicago Midway
6h 02m
1 stop
PIT12:07 amPittsburgh

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from Pittsburgh, with most prices found around $242. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Pittsburgh during the month March is also very affordable. Most momondo users find prices during this month for around $257.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Pittsburgh. The lowest ticket price found for a Tuesday departure recently was $197. 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, Friday 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 $316.

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

Flying to Chicago Midway Airport from Pittsburgh in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $250 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $316. 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 are 1 cabin classes 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.

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

$55

Fastest flight time

1h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Pittsburgh in the past 72 hours is $55. The best round-trip flight deal from Pittsburgh to Chicago Midway Airport found on momondo in the last 72 hours is $120.
The fastest flight from Pittsburgh to Chicago Midway Airport takes 1h 30m
Direct flights go from Pittsburgh to Chicago Midway Airport every day.

  • How far is Pittsburgh to Chicago Midway by plane?

    The straight-line distance from Pittsburgh to Chicago Midway is 413.5 mi. 1h 30m 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 $153Free CancellationRating
8.1
4,659 reviews
Search Southwest flights
DeltaPriceFrom $155Free CancellationRating
8.0
8,521 reviews
Search Delta 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 $153. Generally, Southwest has 19 flights on this route every week with an average price of $304. Southwest is rated 8.1/10 by our users.


Traveling to a place near Chicago?

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


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