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Cheap flights from Pittsburgh to Chicago Midway Airport from $93

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 12/14. 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 to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:15 pm - 7:45 pmPIT-MDW
1h 30mnonstop
10:15 am - 12:35 pmMDW-PIT
1h 20mnonstop
$153Southwest
Find Deal
Di, Jan 21 - Do, Jan 23
9:15 am - 4:00 pmPIT-MDW
7h 45m1 stop
10:15 am - 12:35 pmMDW-PIT
1h 20mnonstop
$162Southwest
Find Deal
Di, Jan 21 - Do, Jan 23
6:30 am - 4:00 pmPIT-MDW
10h 30m2 stops
1:45 pm - 4:05 pmMDW-PIT
1h 20mnonstop
$172Southwest
Find Deal
Di, Jan 21 - Do, Jan 23
6:00 am - 11:58 amPIT-MDW
6h 58m1 stop
4:58 pm - 12:10 amMDW-PIT
6h 12m1 stop
$176Delta
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Di, Dez 10 - Di, Dez 17
6:00 am - 11:08 amPIT-MDW
6h 08m1 stop
6:00 am - 11:43 amMDW-PIT
4h 43m1 stop
$181Delta
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Do, Dez 19 - Di, Jan 7
8:10 am - 8:45 amPIT-MDW
1h 35mnonstop
6:25 pm - 8:45 pmMDW-PIT
1h 20mnonstop
$183Southwest
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Mo, Dez 30 - Mi, Jan 1
12:03 pm - 9:02 pmPIT-MDW
9h 59m1 stop
7:59 pm - 7:07 amMDW-PIT
10h 08m1 stop
$212Frontier
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Do, Feb 20 - So, Feb 23
6:00 am - 5:36 pmPIT-MDW
12h 36m1 stop
6:26 pm - 6:00 pmMDW-PIT
22h 34m3 stops
Do, Mrz 13 - So, Mrz 16
8:35 pm - 12:00 pmPIT-MDW
16h 25m2 stops
9:14 am - 8:15 amMDW-PIT
22h 01m2 stops
Fr, Dez 13 - So, Dez 15
4:05 pm - 1:31 pmPIT-MDW
22h 26m3 stops
2:15 pm - 1:25 pmMDW-PIT
22h 10m3 stops
$1,863WestJet
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Do, Dez 5 - Mo, Dez 9
7:30 am - 11:58 amPIT-MDW
5h 28m1 stop
$93Delta
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Sa, Dez 14
4:30 pm - 9:15 pmPIT-MDW
5h 45m1 stop
$108Southwest
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Di, Dez 31
1:45 pm - 7:35 pmPIT-MDW
6h 50m2 stops
$113Southwest
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Di, Dez 31
7:55 pm - 8:25 pmPIT-MDW
1h 30mnonstop
$114Southwest
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Mo, Feb 24
5:58 pm - 9:55 pmPIT-MDW
4h 57m1 stop
$134Frontier
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Fr, Feb 14
9:00 am - 5:46 pmPIT-MDW
9h 46m1 stop
$140Allegiant Air
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Di, Mrz 11
6:23 am - 8:50 amPIT-MDW
3h 27m1 stop
$147Delta
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Do, Nov 28
9:00 am - 5:46 pmPIT-MDW
9h 46m1 stop
$160Allegiant Air
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Di, Mrz 18
5:58 pm - 9:55 pmPIT-MDW
4h 57m1 stop
$169Frontier
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Mo, Mrz 10
5:07 pm - 1:31 pmPIT-MDW
21h 24m3 stops
$592WestJet
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So, Dez 15
8:20 am - 8:55 amPIT-MDW
1h 35mnonstop
1:20 pm - 3:40 pmMDW-PIT
1h 20mnonstop
$470Southwest
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Di, Nov 19 - Di, Nov 26
6:15 am - 2:15 pmPIT-MDW
9h 00m1 stop
1:20 pm - 3:40 pmMDW-PIT
1h 20mnonstop
$479Southwest
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Di, Nov 19 - Di, Nov 26
1:45 pm - 7:50 pmPIT-MDW
7h 05m2 stops
8:25 pm - 10:45 pmMDW-PIT
1h 20mnonstop
$484Southwest
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Di, Nov 19 - So, Nov 24
6:23 am - 8:50 amPIT-MDW
3h 27m1 stop
6:49 pm - 12:07 amMDW-PIT
4h 18m1 stop
$488Delta
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Sa, Nov 16 - Fr, Nov 22
8:55 pm - 9:25 pmPIT-MDW
1h 30mnonstop
3:15 pm - 11:40 pmMDW-PIT
7h 25m2 stops
$489Southwest
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Mo, Nov 18 - Sa, Nov 23
8:55 pm - 9:25 pmPIT-MDW
1h 30mnonstop
8:20 am - 10:40 amMDW-PIT
1h 20mnonstop
$500Southwest
Find Deal
Mo, Nov 18 - Do, Nov 21
8:55 pm - 9:25 pmPIT-MDW
1h 30mnonstop
4:00 pm - 11:30 pmMDW-PIT
6h 30m1 stop
$509Southwest
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Mo, Nov 18 - Do, Nov 21
6:18 pm - 9:46 pmPIT-MDW
4h 28m1 stop
6:49 pm - 12:07 amMDW-PIT
4h 18m1 stop
$682Delta
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Fr, Nov 15 - So, Nov 17
7:00 am - 5:02 pmPIT-MDW
11h 02m2 stops
6:00 am - 8:19 pmMDW-PIT
13h 19m2 stops
$862Delta
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Di, Nov 19 - Mi, Nov 20
5:15 am - 8:45 amPIT-MDW
28h 30m3 stops
7:50 pm - 5:46 pmMDW-PIT
20h 56m2 stops
$1,070
Find Deal
So, Nov 17 - Di, Nov 19
7:15 pm - 7:45 pmPIT-MDW
1h 30mnonstop
10:15 am - 12:35 pmMDW-PIT
1h 20mnonstop
$153Southwest
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Di, Jan 21 - Do, Jan 23
8:10 am - 8:45 amPIT-MDW
1h 35mnonstop
6:25 pm - 8:45 pmMDW-PIT
1h 20mnonstop
$183Southwest
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Mo, Dez 30 - Mi, Jan 1
5:55 pm - 6:30 pmPIT-MDW
1h 35mnonstop
1:45 pm - 4:05 pmMDW-PIT
1h 20mnonstop
$198Southwest
Find Deal
Sa, Jan 11 - Mo, Jan 13
7:15 pm - 7:45 pmPIT-MDW
1h 30mnonstop
8:40 am - 11:05 amMDW-PIT
1h 25mnonstop
$247Southwest
Find Deal
Do, Jan 30 - So, Feb 2
8:20 am - 8:55 amPIT-MDW
1h 35mnonstop
8:30 am - 10:55 amMDW-PIT
1h 25mnonstop
$250Southwest
Find Deal
Fr, Dez 6 - Di, Dez 10
7:10 pm - 7:40 pmPIT-MDW
1h 30mnonstop
8:05 am - 10:30 amMDW-PIT
1h 25mnonstop
$252Southwest
Find Deal
Mi, Dez 25 - So, Dez 29
8:55 pm - 9:25 pmPIT-MDW
1h 30mnonstop
4:50 pm - 7:10 pmMDW-PIT
1h 20mnonstop
$277Southwest
Find Deal
Fr, Dez 13 - Sa, Dez 14
7:10 pm - 7:40 pmPIT-MDW
1h 30mnonstop
8:20 am - 10:40 amMDW-PIT
1h 20mnonstop
$295Southwest
Find Deal
Do, Dez 5 - So, Dez 8
9:25 pm - 9:55 pmPIT-MDW
1h 30mnonstop
8:05 am - 10:30 amMDW-PIT
1h 25mnonstop
$297Southwest
Find Deal
Fr, Dez 27 - Mo, Dez 30
7:05 am - 7:40 amPIT-MDW
1h 35mnonstop
1:05 pm - 3:25 pmMDW-PIT
1h 20mnonstop
$326Southwest
Find Deal
Fr, Jan 10 - So, Jan 12

Southwest flights from Pittsburgh to Chicago Midway Airport

Our best Southwest deals on Pittsburgh to Chicago Midway Airport flight tickets
Southwest
Jan 21
PIT7:15 pmPittsburgh
1h 30m
MDW7:45 pmChicago Midway
Jan 23
MDW10:15 amChicago Midway
1h 20m
PIT12:35 pmPittsburgh
Southwest
Jan 21
PIT9:15 amPittsburgh
7h 45m
1 stop
MDW4:00 pmChicago Midway
Jan 23
MDW10:15 amChicago Midway
1h 20m
PIT12:35 pmPittsburgh
Southwest
Jan 21
PIT6:30 amPittsburgh
10h 30m
2 stops
MDW4:00 pmChicago Midway
Jan 23
MDW1:45 pmChicago Midway
1h 20m
PIT4:05 pmPittsburgh

Delta flights from Pittsburgh to Chicago Midway Airport

Our best Delta deals on Pittsburgh to Chicago Midway Airport flight tickets
Delta
Dec 10
PIT6:00 amPittsburgh
6h 58m
1 stop
MDW11:58 amChicago Midway
Dec 17
MDW4:58 pmChicago Midway
6h 12m
1 stop
PIT12:10 amPittsburgh
Delta
Dec 19
PIT6:00 amPittsburgh
6h 08m
1 stop
MDW11:08 amChicago Midway
Jan 7
MDW6:00 amChicago Midway
4h 43m
1 stop
PIT11:43 amPittsburgh
Delta
Jan 11
PIT6:30 amPittsburgh
3h 24m
1 stop
MDW8:54 amChicago Midway
Jan 13
MDW9:34 amChicago Midway
2h 51m
1 stop
PIT1:25 pmPittsburgh

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 from Pittsburgh to Chicago Midway Airport?

March. The cheapest time of year to fly to Chicago Midway Airport from Pittsburgh is March. Most expensive is May

What is the cheapest day to depart Pittsburgh for Chicago Midway Airport?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Saturday

When is the cheapest time to fly from Pittsburgh to Chicago Midway Airport?

In the afternoon. Pittsburgh to Chicago Midway Airport flights are approximately 21% more expensive at noon than in the afternoon

What is the cheapest airline that flies to Chicago Midway Airport from Pittsburgh?

Southwest. Southwest and Delta are the most popular carriers operating from Pittsburgh to Chicago Midway Airport

How many flights depart from Pittsburgh to Chicago Midway Airport on average per day?

As of November 2024, 2 flights take off from Pittsburgh and land in Chicago Midway Airport each day. The most common flight departure time for this route is 7:00AM, with 35% of daily flights taking off at noon.

How many flights depart from Pittsburgh to Chicago Midway Airport on average per week?

As of November 2024, 18 flights take off from Pittsburgh and land in Chicago Midway Airport each week. The most common flight departure day for this route is Sunday, with 17% of weekly flights taking off on this day.

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

You could potentially save up to 23% 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

$93

Fastest flight time

1h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Pittsburgh in the past 72 hours is $93. The best round-trip flight deal from Pittsburgh to Chicago Midway Airport found on momondo in the last 72 hours is $153.
The fastest flight from Pittsburgh to Chicago Midway Airport takes 1h 25m
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 25m 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 $148Free CancellationRating
8.1
5,045 reviews
Search Southwest flights
DeltaPriceFrom $155Free CancellationRating
8.0
8,788 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 $148. Generally, Southwest has 18 flights on this route every week with an average price of $286. Southwest is rated 8.1/10 by our users.


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.

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