$50+ Cheap flights from Pittsburgh (PIT) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — CHI
Feb 15 — Feb 221
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Pittsburgh to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.The best prices from Pittsburgh to Chicago are usually found in August or September, booked 43 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Pittsburgh to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 10, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $153 (CheapOair) |
One-way from | $50 (Frontier) |
Popular in | January |
Cheapest in | August |
Average price | $295 |
Good round-trip deal | $336 or less |
Good one-way deal | $202 or less |
Find flight deals from Pittsburgh to Chicago
Cheapest flights from Pittsburgh to ChicagoExplore the most affordable flight options available from Pittsburgh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 10, 2025.
Explore the most affordable flight options available from Pittsburgh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 10, 2025.
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/711:41 amPIT - ORD
1 stop21h 03mSpirit Airlines
Mon 3/105:22 pmORD - PIT
1 stop16h 14mSpirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$153
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/126:15 amPIT - ORD
1 stop7h 30mSouthwest
Wed 3/121:50 pmORD - PIT
1 stop4h 20mSouthwest
Deal found 2/9![Southwest logo]()
$157
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/209:21 pmPIT - ORD
1 stop11h 29mMultiple Airlines
Wed 4/236:09 pmORD - PIT
1 stop5h 09mMultiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$158
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/85:50 pmPIT - ORD
Nonstop1h 49mUnited Airlines
Wed 3/128:50 amORD - PIT
1 stop4h 21mUnited Airlines
Deal found 2/8![United Airlines logo]()
$162
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/149:10 pmPIT - MDW
Nonstop1h 30mSouthwest
Tue 3/181:30 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 2/9![Southwest logo]()
$172
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/125:59 pmPIT - MDW
1 stop5h 24mDelta
Thu 3/1310:25 amMDW - PIT
1 stop5h 40mDelta
Deal found 2/10![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/77:42 pmPIT - ORD
1 stop5h 07mDelta
Sat 3/156:15 amORD - PIT
1 stop4h 45mDelta
Deal found 2/10![Delta logo]()
$177
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/184:33 pmPIT - ORD
Nonstop1h 44mAmerican Airlines
Mon 3/38:24 amORD - PIT
Nonstop1h 31mAmerican Airlines
Deal found 2/9![American Airlines logo]()
$201
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/173:42 pmPIT - MDW
1 stop6h 58mFrontier
Sun 4/208:00 amMDW - PIT
1 stop5h 42mFrontier
Deal found 2/10![Frontier logo]()
$210
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/288:36 pmPIT - ORD
1 stop13h 39mFrontier
Sun 3/99:25 amORD - PIT
1 stop22h 21mFrontier
Deal found 2/10![Frontier logo]()
$260
This JetBlue deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2511:54 amPIT - ORD
1 stop6h 06mJetBlue
Sat 3/112:38 pmORD - PIT
1 stop9h 13mJetBlue
Deal found 2/10![JetBlue logo]()
$312
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/155:30 pmPIT - RFD
1 stop15h 30mMultiple Airlines
Sun 3/169:37 pmRFD - PIT
2 stops25h 55mMultiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$368
Find flights from Pittsburgh to Chicago within your budget
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, Cheapflights users made 2,558,603 searches. Data last updated February 10, 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 3/7
11:41 am-7:44 am
1 stop21h 03m
Chicago O'Hare Intl
Mon 3/10
5:22 pm-10:36 am
1 stop16h 14m
$153
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Wed 3/12
8:15 am-4:05 pm
1 stop8h 50m
Chicago Midway
Wed 3/12
5:15 pm-11:10 pm
1 stop4h 55m
$157
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Wed 3/12
6:15 am-12:45 pm
1 stop7h 30m
Chicago O'Hare Intl
Wed 3/12
1:50 pm-7:10 pm
1 stop4h 20m
$157
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Sun 4/20
9:21 pm-7:50 am
1 stop11h 29m
Chicago O'Hare Intl
Wed 4/23
6:09 pm-12:18 am
1 stop5h 09m
$158
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Sat 3/8
5:50 pm-6:39 pm
Nonstop1h 49m
Chicago O'Hare Intl
Wed 3/12
8:50 am-2:11 pm
1 stop4h 21m
$162
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Wed 3/12
4:34 pm-10:23 pm
1 stop6h 49m
Chicago Midway
Mon 3/17
6:42 pm-11:05 pm
1 stop3h 23m
$177
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 3/7
7:42 pm-11:49 pm
1 stop5h 07m
Chicago O'Hare Intl
Sat 3/15
6:15 am-12:00 pm
1 stop4h 45m
$177
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Thu 4/17
3:42 pm-9:40 pm
1 stop6h 58m
Chicago Midway
Sun 4/20
8:00 am-2:42 pm
1 stop5h 42m
$185
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Tue 4/15
1:35 pm-7:31 pm
1 stop6h 56m
Chicago O'Hare Intl
Tue 4/22
12:55 pm-3:27 pm
Nonstop1h 32m
$207
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 2/28
8:36 pm-9:15 am
1 stop13h 39m
Chicago O'Hare Intl
Sun 3/9
9:25 am-8:46 am
1 stop22h 21m
$260
Showing 1-10 of 28 results
Compare providers for flights from Pittsburgh to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pittsburgh to Chicago in February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Pittsburgh-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Pittsburgh-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pittsburgh-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Pittsburgh to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pittsburgh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Travel insights for flights from Pittsburgh to Chicago
Get recent, data-driven insights about flights from Pittsburgh to Chicago including ideal travel times, pricing trends, and more.
How far ahead should I book a flight from Pittsburgh to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Pittsburgh to Chicago. Price data was last updated on February 7, 2025.
The price you pay for your flight from Pittsburgh to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 43 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Pittsburgh to Chicago?
Currently, August is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $245). Flying from Pittsburgh to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PIT to CHI?
Find hourly flight availability from Pittsburgh to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 10, 2025.
Unlike at noon, when flights are generally more expensive, you can save up to 39% on flights from Pittsburgh to Chicago by exploring options for tickets in the evening.