CHI - PIT

$69 Find Cheap Flights from Chicago to Pittsburgh

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Pittsburgh departing on 5/20. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Pittsburgh

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pittsburgh, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pittsburgh, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$179
Typical prices: $471-$196
American Airlines
Thu 5/21Mon 5/25
ORD - PIT • Non-stop
Cheapest one-way
$69
Typical prices: $206-$265
Southwest
Wed 5/20
MDW - PIT • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags benefit travelers.
MDW offers a user-friendly experience with short lines.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $179 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
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Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 1h 39m
Direct flights
Direct flights
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+1
Direct flights
Direct flights
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Top routes
Cheapest • 5% average savings
Most popular
Insights
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Avoid delays
Most punctual • 85% on-time
Best time • Fewest delays
Insights
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When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 57% compared to booking last minute.
Insights
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When to travel
Cheapest • 28% price drop
Most popular
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Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Chicago to Pittsburgh (CHI-PIT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Pittsburgh 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 Chicago to Pittsburgh

Thu, May 21 - Mon, May 25
American Airlines Logo
8:27 am - 11:13 am
ORD
-
PIT
1h 46mnonstop
American Airlines Logo
7:59 am - 9:00 am
PIT
-
ORD
2h 01mnonstop
$179American Airlines
Wed, May 27 - Thu, May 28
Southwest Logo
10:10 am - 5:55 pm
MDW
-
PIT
6h 45m
2 stops
Southwest Logo
8:05 pm - 10:45 pm
PIT
-
MDW
3h 40m
1 stop
$182Southwest
Sat, May 30 - Wed, Jun 3
Southwest Logo
1:55 pm - 11:05 pm
ORD
-
PIT
8h 10m
2 stops
Southwest Logo
6:25 am - 12:50 pm
PIT
-
ORD
7h 25m
1 stop
$182Southwest
Thu, May 28 - Thu, Jun 4
Southwest Logo
3:50 pm - 10:15 pm
MDW
-
PIT
5h 25m
1 stop
Southwest Logo
8:10 pm - 8:40 pm
PIT
-
MDW
1h 30mnonstop
$187Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
8:15 am - 12:55 pm
MDW
-
PIT
3h 40m
1 stop
Southwest Logo
6:25 am - 3:45 pm
PIT
-
MDW
10h 20m
2 stops
$188Southwest
Thu, May 21 - Mon, May 25
Delta Logo
1:22 pm - 6:49 pm
MDW
-
PIT
4h 27m
1 stop
Delta Logo
6:30 am - 8:43 am
PIT
-
MDW
3h 13m
1 stop
$197Delta
Thu, May 21 - Mon, May 25
Delta Logo
7:00 am - 11:13 am
ORD
-
PIT
3h 13m
1 stop
Delta Logo
1:00 pm - 6:05 pm
PIT
-
ORD
6h 05m
1 stop
$197Delta
Mon, May 18 - Wed, May 20
Southwest Logo
7:40 am - 10:00 am
MDW
-
PIT
1h 20mnonstop
Southwest Logo
6:40 am - 3:50 pm
PIT
-
MDW
10h 10m
2 stops
$198Southwest
Tue, May 26 - Thu, May 28
American Airlines Logo
6:59 pm - 9:49 pm
ORD
-
PIT
1h 50mnonstop
American Airlines Logo
1:48 pm - 5:40 pm
PIT
-
ORD
4h 52m
1 stop
$202American Airlines
Tue, May 26 - Wed, Jun 3
United Airlines Logo
9:20 pm - 11:59 pm
ORD
-
PIT
1h 39mnonstop
United Airlines Logo
7:24 pm - 8:21 pm
PIT
-
ORD
1h 57mnonstop
$207United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Pittsburgh flights

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

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

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

What is the cheapest Chicago to Pittsburgh flight route?

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

The cheapest return flight from Chicago to Pittsburgh costs $157 on the route between Chicago Midway Airport (MDW) and Pittsburgh (PIT). Over the past month, this route was, on average, 5% cheaper than other Chicago-Pittsburgh routes. The most popular route is between Chicago O'Hare Intl Airport (ORD) and Pittsburgh (PIT).

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

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

When flying from Chicago to Pittsburgh, you should consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Pittsburgh, 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 Chicago to Pittsburgh is September, where tickets cost $67 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $163 and $134 respectively.

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

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 $396, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Pittsburgh, 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 Chicago to Pittsburgh, you should book around 4 weeks before departure, which saves you about 57% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Pittsburgh

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Matt Meltzer

Matt Meltzer

Expert on PIT

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Chicago Midway Airport to Pittsburgh

When to book flights from Chicago to Pittsburgh

Are your dates flexible? Find out the best times to travel from Chicago to Pittsburgh based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Pittsburgh

  • Are there kid-friendly amenities on flights from Chicago Airport to Pittsburgh?

    The on-demand kid-friendly entertainment options offered by Air Canada Airlines make it the preferred airline among travelers flying from Chicago Airport to Pittsburgh in the company of their kids. The airline offers free in-flight Wi-Fi services, allowing your kids to stream their favorite TV shows, video games, and films.

  • Where can I find car rentals from PIT Airport in Pittsburgh?

    Using car rentals is one of the most effective methods of connecting travelers to Pittsburgh’s downtown and city center from PIT Airport. Travelers who plan to rent a car from PIT Airport should consider visiting Hertz Car Rental-Pittsburgh International Airport. This is one car rental agency that offers quality and affordable services to travelers landing at PIT Airport.

  • How do I get to Pittsburgh downtown from PIT Airport?

    Using airport shuttles is the most effective way of connecting travelers to Pittsburgh downtown from PIT Airport. Apart from using airport shuttles, travelers can connect to Pittsburgh downtown from PIT Airport through taxis, rental cars, and buses. PIT Airport provides a list of the approved taxi, shuttle, charter bus services, and limousines that travelers can use to connect from the airport to downtown.

  • Which hotel can I stay in after landing at PIT Airport?

    Travelers who plan to stay in a hotel room after landing at PIT Airport shouldn’t worry. Several hotels offer affordable services to travelers from PIT Airport. One hotel that is easily accessible to travelers landing at PIT Airport is the La Quinta Inn by Wyndham Pittsburgh Airport. This hotel is located along University Blvd, Moon Twp, a 9min drive from PIT Airport. La Quinta Inn provides free airport shuttle and Wi-Fi services.

  • What is the cheapest flight from Chicago to Pittsburgh?

    In the last 3 days, the lowest price for a flight from Chicago to Pittsburgh was $69 for a one-way ticket and $179 for a round-trip.

  • Do I need a passport to fly between Chicago and Pittsburgh?

    No, a passport isn't needed to fly from Chicago to Pittsburgh. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Pittsburgh?

    Chicago is served by 2 major airports and there is only 1 main airport in Pittsburgh. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Pittsburgh.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Pittsburgh?

    American Airlines, and Delta offer inflight Wi-Fi service on the Chicago to Pittsburgh flight route.

  • Which aircraft models fly most regularly from Chicago to Pittsburgh?

    The Airbus A319 is the aircraft model that flies most regularly on the Chicago to Pittsburgh flight route.

  • Which airline alliances offer flights from Chicago to Pittsburgh?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Pittsburgh, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Pittsburgh?

    There are nonstop flights from Chicago to Pittsburgh on a daily basis.

  • Which is the best airline for flights from Chicago to Pittsburgh, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Pittsburgh are Southwest and United Airlines. With an average price for the route of $264 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $338 and an overall rating of 7.4.

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

    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 Chicago to Pittsburgh.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pittsburgh from Chicago 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 Chicago to Pittsburgh?

    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 to Pittsburgh with an airline and back to Chicago with another airline.

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

    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 to Pittsburgh from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Pittsburgh

  • Looking for a cheap flight? 25% of our users found flights on this route for $168 or less one-way and $343 or less round-trip.
  • Persons with reduced mobility don’t have to worry when planning to travel from Chicago Airport to Pittsburgh. O'Hare International Airport (ORD) is one airport in Chicago that provides travelers with reduced mobility curb-to-aircraft wheelchair services. All airlines serving flights from ORD Airport to Pittsburgh International Airport (PIT) have deployed enough personnel across the airport to assist travelers with reduced mobility.
  • Despite ORD Airport being the largest airport in Chicago that serves flights to Pittsburgh, travelers from downtown Chicago prefer Chicago Midway International Airport (MDW) as their departure airport to Pittsburgh. Travelers prefer MDW Airport as their departure airport to Pittsburgh because they experience less traffic, less time on the train, shorter drives, and pay cheaply on Ubers that connect them from downtown Chicago to MDW Airport.
  • Pet lovers have nothing to worry about when planning their flights from Chicago Airport to Pittsburgh. ORD Airport has a pet-friendly policy that allows travelers to remain in the company of their pets. However, the airport advises travelers against removing their pets from their crates or carriers at the airport terminals. The Airport has four pet relief areas.
  • Travelers who plan to catch the earliest flight that departs ORD Airport to Pittsburgh should consider spending their night in a nearby hotel. One hotel that guarantees travelers quick access to ORD Airport is Four Points Hotel by Sheraton Chicago O'Hare Airport. The hotel is located along West Irving Park Rd, Schiller Park, 4 miles away from ORD Airport. It offers free airport shuttle services.
  • If you’re planning to take care of your stomach and read some newspapers while waiting for your flight from ORD Airport to Pittsburgh, consider visiting one of the nearest restaurants. Some of the closest restaurants that offer quality and affordable services to travelers at ORD Airport are Berghoff Café and Tortas Frontera by Rick Bayless Restaurant.

Prefer to fly direct from Chicago to Pittsburgh?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Pittsburgh.
Find which airlines fly direct from Chicago to Pittsburgh Airport, which days they fly and book direct flights.

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

See more direct flights

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

See more direct flights

Reviews of the top 3 airlines serving from Chicago to Pittsburgh

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Pittsburgh. 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 Chicago to Pittsburgh? 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.
8.0
SouthwestOverall score based on 4317 reviews
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

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

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

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

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

The flight was on time and the landing was very smooth. The crew and flight attendants were all very friendly and professional.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

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

Information on your arrival and departure airports

Compare transportation modes for Chicago to Pittsburgh

Transportation modeAverage priceAverage duration
Flights$4681h 20m
Trains$3669h 25m
Buses$13813h 30m