PHL - CHI

$89 Find Cheap Flights from Philadelphia to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Philadelphia to Chicago departing on 5/27. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Philadelphia to Chicago, 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 Philadelphia to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$183
Typical prices: $368-$212
Frontier
Sat 5/2Mon 5/4
PHL - ORD • 1 stop
Cheapest non-stop
$184
Typical prices: $385-$216
Frontier
Fri 5/8Mon 5/11
PHL - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Main Cabin Extra offers early boarding.
Southwest offers two free checked bags, ideal for extra luggage.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $183 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and others. Average duration is 2h 31m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 2% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 90% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 41% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 27% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Philadelphia to Chicago (PHL-CHI)

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

Sat, May 2 - Mon, May 4
Frontier Logo
5:05 am - 11:33 am
PHL
-
ORD
7h 28m
1 stop
Frontier Logo
2:20 pm - 5:34 pm
ORD
-
PHL
2h 14mnonstop
$183Frontier
Sat, Aug 15 - Thu, Aug 20
Frontier Logo
5:06 pm - 6:47 pm
PHL
-
ORD
2h 41mnonstop
Frontier Logo
1:50 pm - 10:29 pm
ORD
-
PHL
7h 39m
1 stop
$184Frontier
Sat, May 23 - Thu, May 28
Frontier Logo
4:35 pm - 10:02 pm
PHL
-
MDW
6h 27m
1 stop
Frontier Logo
6:00 am - 7:14 pm
MDW
-
PHL
12h 14m
1 stop
$185Frontier
Wed, Apr 29 - Fri, May 1
Multiple Airlines Logo
1:30 pm - 12:24 am
PHL
-
ORD
11h 54m
1 stop
Multiple Airlines Logo
2:20 pm - 5:34 pm
ORD
-
PHL
2h 14mnonstop
$185Multiple Airlines
Fri, May 1 - Tue, May 5
Spirit Airlines Logo
6:12 pm - 12:24 am
PHL
-
ORD
7h 12m
1 stop
Spirit Airlines Logo
1:18 pm - 11:32 pm
ORD
-
PHL
9h 14m
1 stop
$186Spirit Airlines
Sun, Apr 26 - Tue, Apr 28
Frontier Logo
5:05 am - 8:52 pm
PHL
-
MDW
16h 47m
1 stop
Frontier Logo
6:10 am - 1:21 pm
MDW
-
PHL
6h 11m
1 stop
$186Frontier
Fri, May 8 - Sun, May 10
Frontier Logo
8:35 pm - 8:32 pm
PHL
-
ORD
24h 57m
1 stop
Frontier Logo
3:44 pm - 12:44 am
ORD
-
PHL
8h 00m
1 stop
$187Frontier
Sat, May 30 - Sun, Jun 7
Frontier Logo
4:35 pm - 10:02 pm
PHL
-
MDW
6h 27m
1 stop
Frontier Logo
6:00 am - 12:25 pm
MDW
-
PHL
5h 25m
1 stop
$187Frontier
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
6:12 pm - 12:24 am
PHL
-
ORD
7h 12m
1 stop
Multiple Airlines Logo
4:28 pm - 1:50 pm
ORD
-
PHL
20h 22m
2 stops
$188Multiple Airlines
Thu, May 28 - Mon, Jun 1
Spirit Airlines Logo
5:45 am - 11:56 pm
PHL
-
ORD
19h 11m
1 stop
Spirit Airlines Logo
7:33 pm - 11:32 pm
ORD
-
PHL
26h 59m
1 stop
$190Spirit Airlines
Booking Insights

KAYAK's insights & trends for Philadelphia to Chicago flights

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

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

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

What is the cheapest Philadelphia to Chicago flight route?

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

The cheapest return flight from Philadelphia to Chicago costs $193 on the route between Philadelphia (PHL) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 2% cheaper than other Philadelphia-Chicago routes. It is also the most popular route.

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

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

Your flight ticket price will generally be cheaper if you fly to Chicago on a Friday and more expensive on a Sunday. On your return trip to Philadelphia, you should consider flying back on a Friday, and avoid Mondays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Philadelphia to Chicago, 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 Philadelphia to Chicago is January, where tickets cost $188 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $352 and $320 respectively.

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

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 $334, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Philadelphia to Chicago, 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 Philadelphia to Chicago, you should book around 4 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Expert advice

Expert advice for your flight from Philadelphia to Chicago

 
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
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, 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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines and PHL

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.

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.

Good to know

Low seasonFebruary
Cheapest flight$89
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Philadelphia to Chicago O'Hare Airport

When to book flights from Philadelphia to Chicago

Are your dates flexible? Find out the best times to travel from Philadelphia to Chicago 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 Philadelphia to Chicago

  • What is the cheapest flight from Philadelphia to Chicago?

    In the last 3 days, the lowest price for a flight from Philadelphia to Chicago was $89 for a one-way ticket and $183 for a round-trip.

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

    No

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

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

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Philadelphia to Chicago flight route.

  • Which airline alliances offer flights from Philadelphia to Chicago?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Philadelphia to Chicago are Southwest and United Airlines. With an average price for the route of $280 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 $303 and an overall rating of 7.4.

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

    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 Philadelphia to Chicago.

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

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

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

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

    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 Chicago from Philadelphia 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 Philadelphia to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $186 or less one-way and $311 or less round-trip.

Prefer to fly direct from Philadelphia to Chicago?

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

Direct departures

Philadelphia to Chicago

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 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,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Direct returns

Chicago to Philadelphia

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 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,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Reviews of the top 4 airlines serving from Philadelphia to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Philadelphia to Chicago. 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 Philadelphia to Chicago? 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 4331 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

The new boarding process was easy and straightforward. Very pleasant.

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

I appreciate that I finally got the seat I paid extra for this time. Thank you

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

It would have been nice if American tried to care.

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

They are always late and seats was also not having working charger

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

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

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

Other airlines flying from Philadelphia to Chicago

Flights from the other most popular airlines that fly from Philadelphia to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

Compare transportation modes for Philadelphia to Chicago

Transportation modeAverage priceAverage duration
Flights$7412h 05m
Trains$40227h 10m