$69 Find Cheap Flights from Pittsburgh to Illinois - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pittsburgh to Illinois departing on 8/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Pittsburgh to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago2 stops$168
Moline
Moline1 stop$309
Springfield
Springfield1 stop$563
St. Louis
St. Louis1 stop$196
Chicago
Chicago2 stops$168
Moline
Moline1 stop$309
Springfield
Springfield1 stop$563
St. Louis
St. Louis1 stop$196

Book Cheap Pittsburgh to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pittsburgh to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pittsburgh to Illinois

Tue, Aug 25 - Sat, Aug 29
Southwest Logo
6:30 am - 4:50 pm
PIT
-
MDW
11h 20m
2 stops
Southwest Logo
11:00 am - 6:35 pm
MDW
-
PIT
6h 35m
1 stop
$168Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
4:40 pm - 5:05 pm
PIT
-
MDW
1h 25mnonstop
Southwest Logo
10:30 am - 5:40 pm
MDW
-
PIT
6h 10m
1 stop
$169Southwest
Mon, Aug 24 - Wed, Aug 26
Delta Logo
6:35 am - 9:17 am
PIT
-
MDW
3h 42m
1 stop
Delta Logo
1:25 pm - 7:02 pm
MDW
-
PIT
4h 37m
1 stop
$179Delta
Sat, Aug 8 - Mon, Aug 10
Delta Logo
5:56 pm - 8:30 pm
PIT
-
ORD
3h 34m
1 stop
Delta Logo
7:30 pm - 12:04 am
ORD
-
PIT
3h 34m
1 stop
$179Delta
Thu, Aug 20 - Mon, Aug 24
United Airlines Logo
7:00 am - 7:43 am
PIT
-
ORD
1h 43mnonstop
United Airlines Logo
10:36 am - 1:15 pm
ORD
-
PIT
1h 39mnonstop
$181United Airlines
Tue, Sep 1 - Wed, Sep 2
JetBlue Logo
12:48 pm - 7:26 pm
PIT
-
ORD
7h 38m
1 stop
JetBlue Logo
11:01 am - 6:10 pm
ORD
-
PIT
6h 09m
1 stop
$187JetBlue
Tue, Aug 11 - Thu, Aug 13
United Airlines Logo
6:13 pm - 10:00 pm
PIT
-
STL
4h 47m
1 stop
United Airlines Logo
8:00 am - 1:15 pm
STL
-
PIT
4h 15m
1 stop
$196United Airlines
Mon, Aug 17 - Wed, Aug 19
American Airlines Logo
5:42 pm - 9:28 pm
PIT
-
STL
4h 46m
1 stop
American Airlines Logo
9:15 am - 2:57 pm
STL
-
PIT
4h 42m
1 stop
$201American Airlines
Tue, Jul 28 - Fri, Jul 31
JetBlue Logo
11:53 am - 7:15 pm
PIT
-
ORD
8h 22m
1 stop
JetBlue Logo
5:27 pm - 11:46 pm
ORD
-
PIT
5h 19m
1 stop
$202JetBlue
Tue, Jul 28 - Tue, Aug 4
American Airlines Logo
5:35 am - 10:35 am
PIT
-
STL
6h 00m
1 stop
American Airlines Logo
5:58 pm - 12:07 am
STL
-
PIT
5h 09m
1 stop
$215American Airlines
Booking Insights

KAYAK's insights & trends for Pittsburgh to Illinois flights

Get data-powered insights and trends into flights from Pittsburgh to Illinois to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Pittsburgh to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Pittsburgh to Illinois departing in August.

What is the cheapest Pittsburgh to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Pittsburgh found in the last 5 days was to Chicago, at $137 round-trip. The most popular route is from Pittsburgh (PIT) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $277.

What is the cheapest time of day to fly to Illinois?

The average price for all round-trip flights from Pittsburgh to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $409 on average. Morning departures are around 7% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $561.

Can I save money by flying with a layover from Pittsburgh to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $329, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Pittsburgh to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pittsburgh to Illinois, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Pittsburgh to Illinois is August, when tickets cost $61 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $145 and $137 respectively.

What’s the cheapest day of the week to fly from Pittsburgh to Illinois?

The average price of all round-trip flights from Pittsburgh to Illinois clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Pittsburgh to Illinois, look for departures on Fridays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Illinois, Thursday is the cheapest day to fly and Monday is the most expensive.

How far in advance should I book a flight from Pittsburgh to Illinois?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Pittsburgh to Illinois, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Pittsburgh to Illinois, you should book around 4 weeks before departure, which saves you about 63% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Pittsburgh to Chicago Midway Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Pittsburgh to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Pittsburgh to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pittsburgh to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pittsburgh to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Pittsburgh to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Pittsburgh to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pittsburgh to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Pittsburgh to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Pittsburgh to the following destinations at these prices or less: Chicago $246 one-way - $389 round-trip

Reviews of the top 4 airlines serving from Pittsburgh to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Pittsburgh to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Pittsburgh to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

I really wish that SW would ask anyone with a carry-on to wait while those who don’t have to access the overhead bins are boarded. Then, reverse that when the plane arrives. Those without the need to clog up the aisle retrieving their bags from the overhead bins wait for those exiting the plane without needing to clog up. The aisle.

We boarded the flight and set two and a half hours on the jetway. Would have been better if they had not boarded us at all. Plane was hot and it was limited ability to access the restrooms or get a drink of water. Very unpleasant experience

The actual flight was great! The 3 hour delay not so much.

Southwest is a garbage airline and the people who fly it are garbage people.

Boarding was easy. Plane wasn’t crowded. Plenty of space. Flight was on time. Crew was pleasant.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

A three (3) hour flight should have meal service in First Class, not just potato chips!

Crew were fine, drinks and snacks were as well but we were delayed for around 2 hrs which made our entry into Mexico delayed as well with the influx of arrivals at the same time. Sort of wasted our first day of vacation. We left Pittsburgh at 630am and did not arrive in Mexico until late dinner time.

Seats suck. Only one drink service in three hours with the flight attendants being more attendant to their phones than the customer. Painful in the extreme.

Seat comfort was poor (no lumbar or lower back support).

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Excellent - explanations were clear staff was nice and flight was comfortable

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The American flight was a connecting flight to an international flight. The international flight has a 2 check bag rule. Despite being informed of this, American would only check 1 bag and wanted 100 to check the second (basically a 3rd carry-on) to NYC. Subsequently tsa took a sealed container of maple syrup and a few other things that couldn't be in carry-on plus I had to lug around 3 pieces of luggage for the entire trip. The American reservation was made with the international and American actually checked the one piece the entire way to China. This is one of the reasons that I will avoid American airlines if possible in the future.

Our 9:10 am scheduled flight continued to get delayed all day with no information given from the agents as to why. It wasn’t until I went to the customer service desk and got us switched to another flight at 2:44 pm (that wasn’t nonstop like our booked flight) that the agent finally was able to find out it was due to a fuel leak. I don’t know if our original flight ever took off but I don’t find it acceptable to leave people sitting in an airport all day with no explanation.

This flight was awful all around. Delays on the tarmac at PHL before takeoff and at the tarmac in Chicago caused me to miss my final connection. This was completely avoidable, in my opinion.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

It was a good flight. Of course it was full, but it went well.

Great flight. Quick boarding and departure. No problems. Flight crew were very friendly and professional.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

25 dollars to get a boarding pass abusive nasty folks at the boarding pass check-in desk flight delayed abusive nasty personnel at gate no one knew what they were doing at boarding a real cluster fbk I took a different flight back frontier socks

Everything you need to know for your flight from Pittsburgh to Illinois

Information on your arrival and departure airports