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Cheap Flights from Pittsburgh, PA to Chicago, IL

More cheap flights from Pittsburgh  |  Cheap flights to Chicago
Price Drop

Now is a good time to buy!
Prices from Pittsburgh to Chicago have recently dropped by 40%. more

Price Drop 40%

We track the prices of flights between all major cities searched by priceline customers. We recently saw a change in prices for the route you searched. Compared to the average cost of a ticket in the past, prices are now up to 40% lower.


  • See Historic Prices
  • See the Top 50 best savings routes

best days to fly from Pittsburgh, PA (PIT) to Chicago, IL (MDW, ORD)

My Trip is:

Choose your departure date:

July 2016

What is a Best Day to Fly?

When it comes time to choose your travel dates, we help you find the lowest possible prices by coloring the best days to fly green. To qualify as a best day to fly, the departure or return date must feature a price that is relatively better than other dates around the same time. But please remember that we often do not display a price for every travel date. When this happens, we display the word "price". Airfares may still be available on these dates. Simply click the word "price" to search our latest prices. To locate the best possible deals, you may wish to search a few days before and after your desired departure or return date to avoid peak travel days.


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Full fare, you're going down. Way down. Especially on green days. Or when fares drop.

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* Lowest available retail fare based on recent customer searches. Price may no longer be available.

Inside track to Name Your Own Price®

  Pittsburgh to Chicago

Great Flight Deals from Pittsburgh, PA (PIT) to Chicago, IL (MDW, ORD) start here:

Name Your Own Price® Now!

Choose your departure and return dates and we'll help you book the best flight deal.

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Recent Winning Bids from Pittsburgh to Chicago


About Name Your Own Price

Every day, we look at a sample of winning bids placed by customers using priceline's exclusive Name Your Own Price® option. We identify each winning bid's savings over retail by comparing the bid to the price of a comparable retail ticket. We then look at the collection of recent winning bids and calculate the typical savings for the route as a whole.

We calculate the percentage of non-stop/1-stop flights, time between flights, and typical departure times by looking at the most recent winning bids for each route.

Please remember: just because one of our customers enjoyed great savings or got a non-stop flight, other customers may not get the same deal. Our prices and inventory change constantly.

Bought In
Jayanth G's Trip Sat 7 days $433 $152 65%
Ahmedov R's Trip Fri 1 days $196 $171 13%
Javaneh J's Trip Thu 6 days $258 $217 16%
Audrius L's Trip Sun 6 days $258 $217 16%
Joseph S's Trip Fri 4 days $505 $218 57%
Gauravkumar P's Trip Wed 4 days $218 $127 42%
Rikita S's Trip Fri 8 days $423 $178 58%
Valeria B's Trip Sat 3 days $258 $225 13%
Melissa G's Trip Thu 14 days $338 $129 62%
Daria M's Trip Fri 6 days $218 $177 19%
Best Price and Quality Guarantee
When you Name Your Own Price® for airline tickets you can expect to save up to 40% over other leading sites. And we guarantee in writing that you'll always get the best possible price on your flight. Learn more

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