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Cheap flights from Pittsburgh to Chicago from $49

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 10/6. 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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Cheap round-trip flights

Southwest Logo
6:25 am - 6:50 amPIT-MDW
1h 25mnonstop
Southwest Logo
9:15 pm - 11:40 pmMDW-PIT
1h 25mnonstop
$97Southwest
Find Deal
Thu, Sep 25 - Mon, Sep 29
Southwest Logo
6:25 am - 6:50 amPIT-MDW
1h 25mnonstop
Southwest Logo
6:30 am - 11:00 amMDW-PIT
3h 30m1 stop
$107Southwest
Find Deal
Thu, Sep 25 - Mon, Sep 29
Southwest Logo
4:15 pm - 4:40 pmPIT-MDW
1h 25mnonstop
Southwest Logo
9:15 am - 6:20 pmMDW-PIT
8h 05m2 stops
$112Southwest
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Thu, Sep 25 - Mon, Sep 29
Southwest Logo
8:45 pm - 12:05 amPIT-MDW
4h 20m1 stop
Southwest Logo
5:15 am - 11:45 amMDW-PIT
5h 30m1 stop
$117Southwest
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Thu, Feb 26 - Sat, Feb 28
Frontier Logo
5:40 pm - 12:36 amPIT-MDW
7h 56m1 stop
Frontier Logo
8:25 am - 1:41 pmMDW-PIT
4h 16m1 stop
$144Frontier
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Sun, Oct 12 - Thu, Oct 16
Frontier Logo
9:34 am - 9:51 amPIT-MDW
25h 17m1 stop
Frontier Logo
8:15 am - 1:32 pmMDW-PIT
4h 17m1 stop
$152Frontier
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Fri, Sep 19 - Mon, Sep 22
Delta Logo
6:00 am - 9:48 amPIT-MDW
4h 48m1 stop
Delta Logo
4:23 pm - 12:32 amMDW-PIT
7h 09m1 stop
$177Delta
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Sat, Oct 4 - Sat, Oct 11
Logo
7:12 am - 11:25 pmPIT-MDW
17h 13m2 stops
Logo
8:25 am - 1:41 pmMDW-PIT
4h 16m1 stop
$193
Find Deal
Tue, Oct 7 - Thu, Oct 16
Logo
3:50 pm - 2:51 pmPIT-MDW
24h 01m2 stops
Logo
8:15 am - 1:32 pmMDW-PIT
4h 17m1 stop
$194
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Thu, Sep 18 - Mon, Sep 22
Delta Logo
1:00 pm - 6:25 pmPIT-MDW
6h 25m1 stop
Delta Logo
12:48 pm - 7:10 pmMDW-PIT
5h 22m1 stop
$228Delta
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Thu, Oct 16 - Tue, Oct 21

Frontier flights from Pittsburgh to Chicago Midway Airport

Our best Frontier deals on Pittsburgh to Chicago Midway Airport flight tickets
Frontier
Oct 12
PIT5:40 pmPittsburgh
7h 56m
1 stop
MDW12:36 amChicago Midway
Oct 16
MDW8:25 amChicago Midway
4h 16m
1 stop
PIT1:41 pmPittsburgh
$144
Find similar
Frontier
Sep 19
PIT9:34 amPittsburgh
25h 17m
1 stop
MDW9:51 amChicago Midway
Sep 22
MDW8:15 amChicago Midway
4h 17m
1 stop
PIT1:32 pmPittsburgh
$152
Find similar
Frontier
Sep 19
PIT9:34 amPittsburgh
25h 17m
1 stop
MDW9:51 amChicago Midway
Sep 22
MDW8:15 amChicago Midway
4h 17m
1 stop
PIT1:32 pmPittsburgh
$157
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Southwest flights from Pittsburgh to Chicago Midway Airport

Our best Southwest deals on Pittsburgh to Chicago Midway Airport flight tickets
Southwest
Sep 25
PIT6:25 amPittsburgh
1h 25m
MDW6:50 amChicago Midway
Sep 29
MDW9:15 pmChicago Midway
1h 25m
PIT11:40 pmPittsburgh
$97
Find similar
Southwest
Sep 25
PIT6:25 amPittsburgh
1h 25m
MDW6:50 amChicago Midway
Sep 29
MDW6:30 amChicago Midway
3h 30m
1 stop
PIT11:00 amPittsburgh
$107
Find similar
Southwest
Sep 25
PIT4:15 pmPittsburgh
1h 25m
MDW4:40 pmChicago Midway
Sep 29
MDW9:15 amChicago Midway
8h 05m
2 stops
PIT6:20 pmPittsburgh
$112
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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 September 4, 2025.
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

Thu 9/25

6:25 am-6:50 am

Nonstop1h 25m

Chicago Midway

Mon 9/29

9:15 pm-11:40 pm

Nonstop1h 25m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 9/25

6:25 am-6:50 am

Nonstop1h 25m

Chicago Midway

Mon 9/29

6:30 am-11:00 am

1 stop3h 30m

$107

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 9/25

4:15 pm-4:40 pm

Nonstop1h 25m

Chicago Midway

Mon 9/29

9:15 am-6:20 pm

2 stops8h 05m

$112

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 2/26

8:45 pm-12:05 am

1 stop4h 20m

Chicago Midway

Sat 2/28

5:15 am-11:45 am

1 stop5h 30m

$117

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sun 10/12

5:40 pm-12:36 am

1 stop7h 56m

Chicago Midway

Thu 10/16

8:25 am-1:41 pm

1 stop4h 16m

$144

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 9/19

9:34 am-9:51 am

1 stop25h 17m

Chicago Midway

Mon 9/22

8:15 am-1:32 pm

1 stop4h 17m

$152

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/4

6:00 am-9:48 am

1 stop4h 48m

Chicago Midway

Sat 10/11

4:23 pm-12:32 am

1 stop7h 09m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 10/7

7:12 am-11:25 pm

2 stops17h 13m

Chicago Midway

Thu 10/16

8:25 am-1:41 pm

1 stop4h 16m

$193

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 9/18

3:50 pm-2:51 pm

2 stops24h 01m

Chicago Midway

Mon 9/22

8:15 am-1:32 pm

1 stop4h 17m

$194

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 10/16

1:00 pm-6:25 pm

1 stop6h 25m

Chicago Midway

Tue 10/21

12:48 pm-7:10 pm

1 stop5h 22m

$228

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $233. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Pittsburgh during the month December is also very affordable. Most momondo users find prices during this month for around $242.

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 $372. 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, Saturday 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 $437.

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 $353 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $402. 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.

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 25m

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 $251.
The fastest flight from Pittsburgh to Chicago Midway Airport takes 1h 25m
Direct flights go from Pittsburgh to Chicago Midway Airport every day.
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  • 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 $97Free CancellationRating
8.0
4,242 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 21 flights on this route every week with an average price of $318. 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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

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