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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 10/14. 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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Cheap round-trip flights

Southwest Logo
6:45 pm - 7:15 pmPIT-MDW
1h 30mnonstop
Southwest Logo
10:05 am - 12:25 pmMDW-PIT
1h 20mnonstop
$97Southwest
Find Deal
Tue, Oct 14 - Wed, Oct 15
United Airlines Logo
5:56 pm - 6:40 pmPIT-ORD
1h 44mnonstop
United Airlines Logo
7:25 am - 10:02 amORD-PIT
1h 37mnonstop
$97United Airlines
Find Deal
Tue, Oct 14 - Wed, Oct 15
American Airlines Logo
7:17 am - 7:59 amPIT-ORD
1h 42mnonstop
American Airlines Logo
8:50 pm - 11:19 pmORD-PIT
1h 29mnonstop
$98American Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
American Airlines Logo
7:17 am - 7:59 amPIT-ORD
1h 42mnonstop
American Airlines Logo
8:50 pm - 11:19 pmORD-PIT
1h 29mnonstop
$99American Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
Southwest Logo
6:45 pm - 7:15 pmPIT-MDW
1h 30mnonstop
Southwest Logo
7:55 am - 12:25 pmMDW-PIT
3h 30m1 stop
$107Southwest
Find Deal
Tue, Oct 14 - Wed, Oct 15
Frontier Logo
5:30 pm - 12:16 amPIT-ORD
7h 46m1 stop
Frontier Logo
5:01 am - 1:53 pmORD-PIT
7h 52m1 stop
$144Frontier
Find Deal
Fri, Oct 31 - Sun, Nov 2
United Airlines Logo
2:07 pm - 2:51 pmPIT-ORD
1h 44mnonstop
United Airlines Logo
2:15 pm - 4:52 pmORD-PIT
1h 37mnonstop
$155United Airlines
Find Deal
Tue, Oct 7 - Thu, Oct 9
Frontier Logo
6:51 pm - 10:26 amPIT-MDW
16h 35m1 stop
Frontier Logo
10:12 am - 5:50 pmMDW-PIT
6h 38m1 stop
$156Frontier
Find Deal
Fri, Oct 31 - Sun, Nov 2
Spirit Airlines Logo
6:45 am - 6:38 pmPIT-ORD
12h 53m1 stop
Spirit Airlines Logo
7:43 pm - 11:16 pmORD-PIT
26h 33m1 stop
$182Spirit Airlines
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Tue, Oct 7 - Fri, Oct 17
Spirit Airlines Logo
6:45 am - 11:45 pmPIT-ORD
18h 00m1 stop
Spirit Airlines Logo
11:55 am - 11:16 pmORD-PIT
10h 21m1 stop
$184Spirit Airlines
Find Deal
Wed, Oct 15 - Sat, Oct 18

American Airlines flights from Pittsburgh to Chicago

Our best American Airlines deals on Pittsburgh to Chicago flight tickets
American Airlines
Oct 9
PIT7:17 amPittsburgh
1h 42m
ORD7:59 amChicago O'Hare Intl
Oct 13
ORD8:50 pmChicago O'Hare Intl
1h 29m
PIT11:19 pmPittsburgh
$98
Find similar
American Airlines
Oct 9
PIT7:17 amPittsburgh
1h 42m
ORD7:59 amChicago O'Hare Intl
Oct 13
ORD8:50 pmChicago O'Hare Intl
1h 29m
PIT11:19 pmPittsburgh
$99
Find similar
American Airlines
Nov 5
PIT6:29 amPittsburgh
1h 55m
ORD7:24 amChicago O'Hare Intl
Nov 6
ORD3:30 pmChicago O'Hare Intl
1h 36m
PIT6:06 pmPittsburgh
$149
Find similar

Frontier flights from Pittsburgh to Chicago

Our best Frontier deals on Pittsburgh to Chicago flight tickets
Frontier
Oct 31
PIT5:30 pmPittsburgh
7h 46m
1 stop
ORD12:16 amChicago O'Hare Intl
Nov 2
ORD5:01 amChicago O'Hare Intl
7h 52m
1 stop
PIT1:53 pmPittsburgh
$144
Find similar
Frontier
Sep 26
PIT9:34 amPittsburgh
11h 10m
1 stop
ORD7:44 pmChicago O'Hare Intl
Sep 29
ORD6:10 amChicago O'Hare Intl
6h 22m
1 stop
PIT1:32 pmPittsburgh
$145
Find similar
Frontier
Oct 31
PIT6:51 pmPittsburgh
16h 35m
1 stop
MDW10:26 amChicago Midway
Nov 2
MDW10:12 amChicago Midway
6h 38m
1 stop
PIT5:50 pmPittsburgh
$156
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Chicago 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 17, 2025.
Use the filters below to find and compare flights from Pittsburgh to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 10/14

6:45 pm-7:15 pm

Nonstop1h 30m

Chicago Midway

Wed 10/15

10:05 am-12:25 pm

Nonstop1h 20m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 10/14

5:56 pm-6:40 pm

Nonstop1h 44m

Chicago O'Hare Intl

Wed 10/15

7:25 am-10:02 am

Nonstop1h 37m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 10/9

7:17 am-7:59 am

Nonstop1h 42m

Chicago O'Hare Intl

Mon 10/13

8:50 pm-11:19 pm

Nonstop1h 29m

$98

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 10/9

7:17 am-7:59 am

Nonstop1h 42m

Chicago O'Hare Intl

Mon 10/13

8:50 pm-11:19 pm

Nonstop1h 29m

$99

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 10/14

6:45 pm-7:15 pm

Nonstop1h 30m

Chicago Midway

Wed 10/15

7:55 am-12:25 pm

1 stop3h 30m

$107

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 10/31

5:30 pm-12:16 am

1 stop7h 46m

Chicago O'Hare Intl

Sun 11/2

5:01 am-1:53 pm

1 stop7h 52m

$144

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 10/7

2:07 pm-2:51 pm

Nonstop1h 44m

Chicago O'Hare Intl

Thu 10/9

2:15 pm-4:52 pm

Nonstop1h 37m

$155

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 10/31

6:51 pm-10:26 am

1 stop16h 35m

Chicago Midway

Sun 11/2

10:12 am-5:50 pm

1 stop6h 38m

$156

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 10/7

6:45 am-6:38 pm

1 stop12h 53m

Chicago O'Hare Intl

Fri 10/17

7:43 pm-11:16 pm

1 stop26h 33m

$182

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 10/15

6:45 am-11:45 pm

1 stop18h 00m

Chicago O'Hare Intl

Sat 10/18

11:55 am-11:16 pm

1 stop10h 21m

$184

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

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?

The month of August is, on average, the cheapest month to fly to Chicago from Pittsburgh, with most prices found around $199. If you’re not able to fly to Chicago in August, then April is your next best option. Flight prices from Pittsburgh to Chicago during April average around $243.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $422. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Pittsburgh to Chicago for around $557.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pittsburgh to Chicago during this time can be as low as $397. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $667.

What is the cheapest Pittsburgh to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Pittsburgh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $309 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Pittsburgh for as low as $202 on momondo.

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

There are 4 cabin classes available to choose from on Pittsburgh to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Pittsburgh to Chicago flight prices changed over time?

As of September 2025, prices for Pittsburgh to Chicago flights are approximately 30% cheaper when compared to flights at the same time last year.

When to book flights from Pittsburgh to Chicago

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

Cheap Pittsburgh to Chicago (PIT to CHI) flight deals and tips

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

Best Price Found

$175

Fastest flight time

1h 25m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Pittsburgh in the past 72 hours is $175. The best round-trip flight deal from Pittsburgh to Chicago found on momondo in the last 72 hours is $272.
The fastest flight from Pittsburgh to Chicago takes 1h 25m
Direct flights go from Pittsburgh to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • How far is Pittsburgh to Chicago by plane?

    Pittsburgh and Chicago are 408.7 mi apart from one another. In terms of flight time, this usually takes a little over 1h 25m.

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

    Prices for flights from Pittsburgh Airport to Chicago are updated daily.

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

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

    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.

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

    The necessary travel and health documents for your Chicago 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?

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

Best airlines flying from Pittsburgh to Chicago

Compare and see reviews for airlines that fly from Pittsburgh to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $93Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $130Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

  • Southwest Flights From Pittsburgh to Chicago

    The lowest priced Southwest flight from Pittsburgh to Chicago from the last 72 hours was $97. Generally, Southwest has 21 flights on this route every week with an average price of $321. Southwest is rated 8.0/10 by our users.

  • United Airlines Flights From Pittsburgh to Chicago

    United Airlines is also a popular choice for this route. United Airlines flight deals for Pittsburgh to Chicago start from as low as $130 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $319. United Airlines operates 42 flights to Chicago from Pittsburgh in an average week. Users have rated it 7.4/10 across 8,926 reviews.

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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Pittsburgh to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Pittsburgh to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Pittsburgh to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Pittsburgh to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport