Southwest offers free carry-on and personal item, but checked bags now incur fees.
Southwest's cancellation policy allows changes up to 10 minutes before departure for credit or refund.
Planning a trip from Chicago to Pittsburgh? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
Low season | January |
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High season | October |
Cheapest flight | $49 |
Direct departures
Chicago to Pittsburgh
Monday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Tuesday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Wednesday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Thursday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Friday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Saturday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Sunday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Direct returns
Pittsburgh to Chicago
Monday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Tuesday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Wednesday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Thursday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Friday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Saturday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Sunday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!
I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!
As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.
The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.
After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app
AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.
Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.
Southwest's seats are the least comfortable I have ever sat in.
The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.
Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.
My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.
Once we got in the air the pilot made up some of the time of the delay. So that was really nice.
Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.
It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.
It was great, I’m very grateful for the pilots and crew flight attendants for everything.
Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick
I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.
The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!
Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.
A bit rush for transit. Food and entertainment are not available
Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.
3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!
After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"
After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.
Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan
Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!
I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.
I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude
Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!
Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.
Staff at the gate were incredibly rude, hostile and threatening. Never fly American Airlines.
No Tumberlence smooth flight. Try to change the menu on Snacks.
It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.
We paid for upgrade seats (3A & 3B) the seats on front and the seats behind us got complimentary water & soda, but we got charged, had to pay for everything. Does not make any sense ?
The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.
Spirit charges you to breathe in their presence. They have you pick and buy your seat in advance and then I got bumped from the seat I paid for because THEY overbooked the flight by a dozen people. they do not provide any entertainment, they do not provide even a small cup of water - you have to pay for everything. I will never fly Spirit again.
why's KAYAK involved? why'd Spirit charge me $19.72 on Apr 28 and $4.49 on May 1 ? And ironically my credit card had to be cancelled after trip due to a bogus charge, wonder if using it on the plane enabled a scammer to get it.
Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.
Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.
Spirit is awful. Too expensive for what you get. Stop nickel and diming.
Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.
Transportation mode | Average price | Average duration |
---|---|---|
Flights | $217 | 1h 20m |
Trains | $160 | 9h 25m |
Buses | $105 | 12h 36m |
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