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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 10/21. 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

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Cheap round-trip flights

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
5:50 am - 11:50 amPIT-ORD
7h 00m1 stop
Southwest Logo
3:10 pm - 9:30 pmORD-PIT
5h 20m1 stop
$117Southwest
Find Deal
Wed, Oct 8 - Tue, Oct 21
Southwest Logo
6:00 am - 12:45 pmPIT-ORD
7h 45m1 stop
Southwest Logo
3:10 pm - 9:30 pmORD-PIT
5h 20m1 stop
$122Southwest
Find Deal
Mon, Oct 20 - Wed, Oct 22
Southwest Logo
6:10 am - 12:45 pmPIT-ORD
7h 35m1 stop
Southwest Logo
1:30 pm - 9:50 pmORD-PIT
7h 20m1 stop
$128Southwest
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Wed, Oct 15 - Sat, Oct 18
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
9:34 am - 7:44 pmPIT-ORD
11h 10m1 stop
Frontier Logo
6:00 am - 2:36 pmORD-PIT
7h 36m1 stop
$169Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Delta Logo
4:33 pm - 10:26 pmPIT-ORD
6h 53m1 stop
Delta Logo
5:20 am - 12:43 pmORD-PIT
6h 23m1 stop
$177Delta
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Tue, Oct 14 - Wed, Oct 15

American Airlines flights from Pittsburgh to Chicago O'Hare Intl Airport

Our best American Airlines deals on Pittsburgh to Chicago O'Hare Intl Airport 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
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Frontier flights from Pittsburgh to Chicago O'Hare Intl Airport

Our best Frontier deals on Pittsburgh to Chicago O'Hare Intl Airport 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 3
PIT9:34 amPittsburgh
11h 10m
1 stop
ORD7:44 pmChicago O'Hare Intl
Oct 5
ORD6:00 amChicago O'Hare Intl
7h 36m
1 stop
PIT2:36 pmPittsburgh
$169
Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

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 - ORD

PITORD

Pittsburgh

Wed 10/8

5:50 am-11:50 am

1 stop7h 00m

Chicago O'Hare Intl

Tue 10/21

3:10 pm-9:30 pm

1 stop5h 20m

$117

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 10/20

6:00 am-12:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Wed 10/22

3:10 pm-9:30 pm

1 stop5h 20m

$122

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 10/15

6:10 am-12:45 pm

1 stop7h 35m

Chicago O'Hare Intl

Sat 10/18

1:30 pm-9:50 pm

1 stop7h 20m

$128

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 - ORD

PITORD

Pittsburgh

Fri 10/3

9:34 am-7:44 pm

1 stop11h 10m

Chicago O'Hare Intl

Sun 10/5

6:00 am-2:36 pm

1 stop7h 36m

$169

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 10/14

4:33 pm-10:26 pm

1 stop6h 53m

Chicago O'Hare Intl

Wed 10/15

5:20 am-12:43 pm

1 stop6h 23m

$177

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 O'Hare Intl 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 typical price of a round-trip flight between Pittsburgh and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Pittsburgh averaging around $279.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $448. This is often the case because there is less demand to fly during this day of the week. 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 $605.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Pittsburgh in the evening is the least expensive time of day to depart. momondo users have found prices as low as $448 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $730. 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 O'Hare Intl flight route?

Fly from Pittsburgh to Chicago O'Hare Intl for the best Pittsburgh - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Pittsburgh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport from Pittsburgh for as low as $202 on momondo.

What cabin class options are available on Pittsburgh to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Pittsburgh to Chicago O'Hare Intl 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 O'Hare Intl Airport flight prices changed over time?

As of September 2025, prices for Pittsburgh to Chicago O'Hare Intl Airport flights are approximately 35% cheaper when compared to flights at the same time last year.

When to book flights from Pittsburgh to Chicago O'Hare Intl Airport

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

Cheap Pittsburgh to Chicago O'Hare Intl Airport (PIT to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pittsburgh to Chicago O'Hare Intl Airport

Best Price Found

$175

Fastest flight time

1h 42m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Pittsburgh in the past 72 hours is $175. The best round-trip flight deal from Pittsburgh to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $298.
The fastest flight from Pittsburgh to Chicago O'Hare Intl Airport takes 1h 42m
Direct flights go from Pittsburgh to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Pittsburgh to Chicago O'Hare Intl by plane?

    Pittsburgh and Chicago O'Hare Intl are 424.1 mi apart from one another. 1h 42m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Pittsburgh Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Pittsburgh Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Pittsburgh Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Pittsburgh Airport to Chicago O'Hare Intl 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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Pittsburgh to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Pittsburgh to Chicago O'Hare Intl Airport?

Best airlines flying from Pittsburgh to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Pittsburgh to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $93Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $130Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

  • United Airlines Flights From Pittsburgh to Chicago O'Hare Intl Airport

    Across 42 United Airlines flights from Pittsburgh to Chicago O'Hare Intl Airport this week, the average price was $319, with the best United Airlines deals starting from $130 round-trip. 8,926 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Pittsburgh to Chicago O'Hare Intl Airport

    Another popular option for Pittsburgh to Chicago O'Hare Intl Airport flights is American Airlines (7.2/10, 10,000 ratings). American Airlines flies from Pittsburgh to Chicago O'Hare Intl Airport around 27 times per week, with deals starting from $93 round-trip and rising to an average price of around $299.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

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?

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 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?

If you are not ready to book a flight from Pittsburgh to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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