PHL - CHI

$87 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 4/9. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$179
Overall average: $287
Frontier
Thu 5/7Sun 5/10
PHL - ORD • 1 stop
Cheapest non-stop
$179
Typical prices: $252-$390
Frontier
Sun 4/19Fri 4/24
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 $179 (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 28m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 3% 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 45% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% 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

Thu, May 7 - Sun, May 10
Frontier Logo
1:32 pm - 7:51 pm
PHL
-
ORD
7h 19m
1 stop
Frontier Logo
7:56 pm - 11:22 pm
ORD
-
PHL
2h 26mnonstop
$179Frontier
Wed, Apr 29 - Wed, May 6
Frontier Logo
11:02 am - 7:31 pm
PHL
-
MDW
9h 29m
1 stop
Frontier Logo
12:04 pm - 7:10 pm
MDW
-
PHL
6h 06m
1 stop
$179Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
1:44 pm - 9:47 pm
PHL
-
ORD
9h 03m
1 stop
Frontier Logo
1:19 pm - 11:57 pm
ORD
-
PHL
9h 38m
1 stop
$180Frontier
Tue, Apr 14 - Wed, Apr 15
Frontier Logo
11:02 am - 10:14 pm
PHL
-
MDW
12h 12m
1 stop
Frontier Logo
2:15 pm - 12:54 am
MDW
-
PHL
9h 39m
1 stop
$180Frontier
Sat, Apr 18 - Tue, Apr 21
Frontier Logo
7:45 am - 4:21 pm
PHL
-
ORD
9h 36m
1 stop
Frontier Logo
6:08 pm - 12:54 am
ORD
-
PHL
5h 46m
1 stop
$181Frontier
Tue, Apr 14 - Thu, Apr 16
Frontier Logo
11:02 am - 7:31 pm
PHL
-
MDW
9h 29m
1 stop
Frontier Logo
6:00 am - 5:49 pm
MDW
-
PHL
10h 49m
1 stop
$181Frontier
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
7:45 am - 2:47 pm
PHL
-
ORD
8h 02m
1 stop
Multiple Airlines Logo
7:15 pm - 9:49 am
ORD
-
PHL
13h 34m
1 stop
$182Multiple Airlines
Tue, Apr 14 - Thu, Apr 16
Frontier Logo
11:02 am - 10:14 pm
PHL
-
MDW
12h 12m
1 stop
Frontier Logo
6:00 am - 5:49 pm
MDW
-
PHL
10h 49m
1 stop
$182Frontier
Sat, May 2 - Mon, May 4
Multiple Airlines Logo
6:12 pm - 12:24 am
PHL
-
ORD
7h 12m
1 stop
Multiple Airlines Logo
9:41 am - 5:38 pm
ORD
-
PHL
6h 57m
1 stop
$183Multiple Airlines
Thu, May 7 - Mon, May 11
Frontier Logo
1:32 pm - 7:51 pm
PHL
-
ORD
7h 19m
1 stop
Frontier Logo
4:05 pm - 3:42 pm
ORD
-
PHL
22h 37m
1 stop
$184Frontier
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.

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 $181 on the route between Philadelphia (PHL) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 3% 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 Sundays 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 $356 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $320 on average.

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 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 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$87
Best time to beat the crowds but there is an average 25% increase in price.
Most popular time to fly and prices are also 16% 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 $87 for a one-way ticket and $179 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 $279 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 $299 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 $195 or less one-way and $326 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,Southwest,United Airlines, +1 more

American Airlines,Southwest, +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,Southwest,United Airlines, +1 more

American Airlines,Southwest, +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 4320 reviews
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

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.

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

The Phildalphia to Allentown portion was a BUS, not a plane. All was as expected.

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.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

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$9382h 10m
Trains$37826h 45m