What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Pittsburgh according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Southwest, Frontier, and JetBlue are the most popular carriers operating from Pittsburgh to Chicago

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

As of November 2025, 43 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 8:00AM, with 53% of daily flights taking off at noon.

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

As of November 2025, 305 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.

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?

There are 3 operators available for flights from Pittsburgh Airport to Chicago as of November 2025.

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.

$69 Cheap Flights from Pittsburgh to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Pittsburgh and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $218 to $387. The lowest price recently found on this route was $137.

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Find the cheapest flights from Pittsburgh to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 12:15 pmPIT-ORD

7h 15m1 stop

1:45 pm - 9:05 pmORD-PIT

6h 20m1 stop

$137Southwest

Find Deal

mié., dic. 3 - mié., dic. 3

5:02 pm - 12:10 amPIT-ORD

8h 08m1 stop

5:30 am - 2:42 pmORD-PIT

8h 12m1 stop

$141Frontier

Find Deal

sáb., nov. 22 - lun., nov. 24

4:53 pm - 5:56 pmPIT-ORD

2h 03mnonstop

6:30 pm - 9:00 pmORD-PIT

1h 30mnonstop

$143American Airlines

Find Deal

mié., dic. 3 - jue., dic. 4

5:05 pm - 12:09 amPIT-ORD

8h 04m1 stop

9:14 pm - 12:41 amORD-PIT

26h 27m2 stops

$148Spirit Airlines

Find Deal

sáb., dic. 13 - mar., dic. 16

8:15 am - 9:07 amPIT-ORD

1h 52mnonstop

12:02 am - 2:45 amORD-PIT

1h 43mnonstop

$149American Airlines

Find Deal

jue., dic. 25 - dom., ene. 4

10:42 pm - 2:57 pmPIT-ORD

17h 15m1 stop

4:22 pm - 12:41 amORD-PIT

31h 19m2 stops

$151Multiple Airlines

Find Deal

mar., dic. 2 - mar., dic. 9

5:05 pm - 12:09 amPIT-ORD

8h 04m1 stop

3:26 pm - 12:41 amORD-PIT

8h 15m1 stop

$153Spirit Airlines

Find Deal

sáb., dic. 6 - mié., dic. 10

10:15 am - 8:27 pmPIT-ORD

11h 12m1 stop

5:30 am - 2:42 pmORD-PIT

8h 12m1 stop

$154Multiple Airlines

Find Deal

mar., nov. 18 - vie., nov. 21

7:00 am - 7:44 amPIT-ORD

1h 44mnonstop

9:05 pm - 11:38 pmORD-PIT

1h 33mnonstop

$159United Airlines

Find Deal

jue., dic. 4 - jue., dic. 4

7:00 am - 7:44 amPIT-ORD

1h 44mnonstop

2:15 pm - 4:45 pmORD-PIT

1h 30mnonstop

$161United Airlines

Find Deal

mar., dic. 9 - mar., dic. 9

Southwest flights from Pittsburgh to Chicago

Our best Southwest deals on Pittsburgh to Chicago flight tickets

Southwest

Dec 3

PIT6:00 amPittsburgh

7h 15m

1 stop

ORD12:15 pmChicago O'Hare Intl

Dec 3

ORD1:45 pmChicago O'Hare Intl

6h 20m

1 stop

PIT9:05 pmPittsburgh

$137

Find similar

Southwest

Dec 6

PIT6:05 pmPittsburgh

1h 30m

MDW6:35 pmChicago Midway

Dec 8

MDW10:15 amChicago Midway

1h 30m

PIT12:45 pmPittsburgh

$160

Find similar

Southwest

Dec 3

PIT2:00 pmPittsburgh

1h 30m

MDW2:30 pmChicago Midway

Dec 6

MDW9:45 amChicago Midway

1h 25m

PIT12:10 pmPittsburgh

$168

Find similar

Frontier flights from Pittsburgh to Chicago

Our best Frontier deals on Pittsburgh to Chicago flight tickets

Frontier

Nov 22

PIT5:02 pmPittsburgh

8h 08m

1 stop

ORD12:10 amChicago O'Hare Intl

Nov 24

ORD5:30 amChicago O'Hare Intl

8h 12m

1 stop

PIT2:42 pmPittsburgh

$141

Find similar

Frontier

Nov 22

PIT5:02 pmPittsburgh

8h 08m

1 stop

ORD12:10 amChicago O'Hare Intl

Nov 24

ORD5:30 amChicago O'Hare Intl

8h 12m

1 stop

PIT2:42 pmPittsburgh

$144

Find similar

Frontier

Nov 10

PIT5:30 pmPittsburgh

7h 45m

1 stop

ORD12:15 amChicago O'Hare Intl

Nov 21

ORD5:30 amChicago O'Hare Intl

8h 12m

1 stop

PIT2:42 pmPittsburgh

$197

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

mié. 12/3

6:00 am-12:15 pm

1 stop7h 15m

Chicago O'Hare Intl

mié. 12/3

1:45 pm-9:05 pm

1 stop6h 20m

$137

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

sáb. 11/22

5:02 pm-12:10 am

1 stop8h 08m

Chicago O'Hare Intl

lun. 11/24

5:30 am-2:42 pm

1 stop8h 12m

$141

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

mié. 12/3

4:53 pm-5:56 pm

Nonstop2h 03m

Chicago O'Hare Intl

jue. 12/4

6:30 pm-9:00 pm

Nonstop1h 30m

$143

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

sáb. 12/13

5:05 pm-12:09 am

1 stop8h 04m

Chicago O'Hare Intl

mar. 12/16

9:14 pm-12:41 am

2 stops26h 27m

$148

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

jue. 12/25

8:15 am-9:07 am

Nonstop1h 52m

Chicago O'Hare Intl

dom. 1/4

12:02 am-2:45 am

Nonstop1h 43m

$149

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

mar. 12/2

10:42 pm-2:57 pm

1 stop17h 15m

Chicago O'Hare Intl

mar. 12/9

4:22 pm-12:41 am

2 stops31h 19m

$151

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

sáb. 12/6

5:05 pm-12:09 am

1 stop8h 04m

Chicago O'Hare Intl

mié. 12/10

3:26 pm-12:41 am

1 stop8h 15m

$153

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

mar. 11/18

10:15 am-8:27 pm

1 stop11h 12m

Chicago O'Hare Intl

vie. 11/21

5:30 am-2:42 pm

1 stop8h 12m

$154

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

jue. 12/4

7:00 am-7:44 am

Nonstop1h 44m

Chicago O'Hare Intl

jue. 12/4

9:05 pm-11:38 pm

Nonstop1h 33m

$159

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

mar. 12/9

7:00 am-7:44 am

Nonstop1h 44m

Chicago O'Hare Intl

mar. 12/9

2:15 pm-4:45 pm

Nonstop1h 30m

$161

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Pittsburgh and Chicago?

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 September is your next best option. Flight prices from Pittsburgh to Chicago during September average around $227.

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 $428. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Pittsburgh to Chicago for around $547.

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 $650.

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 $161 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 November 2025, prices for Pittsburgh to Chicago flights are approximately 11% more expensive 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	$183
Fastest flight time	1h 30m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Pittsburgh in the past 72 hours is $183. The best round-trip flight deal from Pittsburgh to Chicago found on momondo in the last 72 hours is $286.

The fastest flight from Pittsburgh to Chicago takes 1h 30m

Direct flights go from Pittsburgh to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

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 30m.
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?
There are 3 operators available for flights from Pittsburgh Airport to Chicago as of November 2025.
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?
Based on momondo bookings for flights between Pittsburgh and Chicago, the leading plane model is Boeing 737-800, making up 17.61% of the total bookings. Other popular models include Boeing 737 MAX 8 with 12.19%, Embraer 175 (Enhanced Winglets) with 11.30%, and Embraer 175 with 10.99%.
What is the most popular airline from Pittsburgh to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Pittsburgh to Chicago is Southwest (38% of total bookings). The next most popular airlines are United Airlines (33%), American Airlines (27%), and Frontier (1%).

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 Airlines	PriceFrom $92	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,241 reviews	Search Southwest flights
United Airlines	PriceFrom $126	Free Cancellation	Rating 7.4 9,007 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 18 flights on this route every week with an average price of $318. 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 $126 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $322. United Airlines operates 29 flights to Chicago from Pittsburgh in an average week. Users have rated it 7.4/10 across 9,007 reviews.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

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.

An easier way to manage your Chicago 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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sáb. 12/6

sáb. 12/13

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Washington, D.C.from $49

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Flights to Dallasfrom $59

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Flights to Denverfrom $57

Cheap flights from Pittsburgh to Chicago from $69

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 1/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Pittsburgh to Chicago

Cheap round-trip flights

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Cheap last minute flights

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Southwest flights from Pittsburgh to Chicago

Our best Southwest deals on Pittsburgh to Chicago flight tickets

Frontier flights from Pittsburgh to Chicago

Our best Frontier deals on Pittsburgh to Chicago flight tickets

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Use the filters below to find and compare flights from Pittsburgh to Chicago that are best for you.

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 typical price of a round-trip flight between Pittsburgh and Chicago?

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 September is your next best option. Flight prices from Pittsburgh to Chicago during September average around $227.

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

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 $650.

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?

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 November 2025, prices for Pittsburgh to Chicago flights are approximately 11% more expensive when compared to flights at the same time last year.

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

Southwest, Frontier, and JetBlue are the most popular carriers operating from Pittsburgh to Chicago

What airlines fly to Chicago?

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

As of November 2025, 43 flights take off from Pittsburgh and land in Chicago each day. The most common flight departure time for this route is 8:00AM, with 53% of daily flights taking off at noon.

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

As of November 2025, 305 flights take off from Pittsburgh and land in Chicago each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.

When to book flights from Pittsburgh to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Pittsburgh to Chicago by plane?

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

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?

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

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

Southwest Flights From Pittsburgh to Chicago

United Airlines Flights From Pittsburgh to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Pittsburgh to Chicago?

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

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

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

An easier way to manage your Chicago 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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