PHL - CHI

$35 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 10/25. 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

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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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, Sep 11 - Mon, Sep 15
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
$73Frontier
Find Deal
Mon, Sep 29 - Sun, Oct 5
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:06 am - 11:07 amMDW-PHL
2h 01mnonstop
$74Frontier
Find Deal
Thu, Sep 4 - Sun, Sep 7
Frontier Logo
10:21 am - 11:58 amPHL-ORD
2h 37mnonstop
Frontier Logo
6:10 am - 9:25 amORD-PHL
2h 15mnonstop
$75Frontier
Find Deal
Thu, Sep 18 - Sun, Sep 21
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:06 am - 11:07 amMDW-PHL
2h 01mnonstop
$75Frontier
Find Deal
Sat, Sep 13 - Thu, Sep 18
 Logo
5:00 am - 10:52 amPHL-ORD
6h 52m1 stop
 Logo
6:10 am - 9:25 amORD-PHL
2h 15mnonstop
Sat, Sep 13 - Sat, Sep 13
American Airlines Logo
12:36 pm - 2:06 pmPHL-ORD
2h 30mnonstop
American Airlines Logo
4:45 pm - 7:55 pmORD-PHL
2h 10mnonstop
$134American Airlines
Find Deal
Sat, Sep 20 - Wed, Sep 24
Southwest Logo
2:20 pm - 3:25 pmPHL-MDW
2h 05mnonstop
Southwest Logo
10:05 am - 1:05 pmMDW-PHL
2h 00mnonstop
$139Southwest
Find Deal
Sat, Sep 20 - Wed, Sep 24
United Airlines Logo
10:10 am - 11:32 amPHL-ORD
2h 22mnonstop
United Airlines Logo
8:45 am - 11:56 amORD-PHL
2h 11mnonstop
$139United Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 20
Southwest Logo
5:25 pm - 6:35 pmPHL-MDW
2h 10mnonstop
Southwest Logo
6:05 pm - 9:05 pmMDW-PHL
2h 00mnonstop
$154Southwest
Find Deal
Thu, Aug 28 - Fri, Sep 5
 Logo
9:47 am - 2:16 pmPHL-RFD
5h 29m1 stop
 Logo
10:37 am - 11:29 pmRFD-PHL
11h 52m1 stop
Expert advice

Expert advice for your flight from Philadelphia to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Frontier's Economy Bundle includes a carry-on and seat choice, ideal for budget travelers.


Frontier's Premium Bundle offers extra legroom and priority boarding for just $20 more.

Read more about Frontierby Stefanie Waldek
American Airlines

American's Main Cabin Extra offers early boarding and complimentary drinks, enhancing travel comfort.


American's Wi-Fi offers 20 minutes free with an ad, useful for quick tasks.

Southwest

Southwest offers two free checked bags, ideal for travelers with extra luggage.


Southwest's EarlyBird Check-In secures a better boarding position, avoiding middle seats.

Read more about Southwestby Blane Bachelor
United Airlines

United's Economy Plus offers up to six inches more legroom, enhancing comfort on short flights.


United's Wi-Fi allows free messaging; check coverage before purchasing for streaming.

Airports
PHL

For a quick trip to downtown, take SEPTA's Airport Regional Rail Line. It's affordable and takes about 30 minutes.

Read more about PHLby Harriet Baskas
ORD

Take the CTA Blue Line from ORD to downtown Chicago. It's a 45-minute ride and runs 24 hours.

Read more about ORDby Stefanie Waldek
MDW

Use the CTA Orange Line from MDW to reach downtown Chicago in about 25 minutes.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, United Airlines, ORD and MDW

Stefanie Waldek

Stefanie Waldek

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines and PHL

Harriet Baskas

Harriet Baskas

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
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.

Find cheap flights to Chicago
Find cheap flights to Chicago

Planning a trip from Philadelphia to Chicago? 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.

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

What is the cheapest Philadelphia to Chicago flight route?

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

The absolute cheapest return flight from Philadelphia to Chicago costs $124 on the route between Philadelphia (PHL) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Philadelphia (PHL) and Chicago Midway Airport (MDW) were, on average, 2% cheaper than other Philadelphia-Chicago routes. The most popular route is between Philadelphia (PHL) and Chicago O'Hare Intl Airport (ORD).

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 Thursday, 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 September, where tickets cost $134 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $327 and $309 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 $571 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 2 weeks before departure, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$35
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly and prices are also 21% 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

  • Where can I park at Philadelphia Airport?

    You can get long-term parking at the airport's Economy Lot F, which charges about $15-$22 per day. Suppose you need to park your rental car before heading to your departure terminal. In that case, you'll find the designated car-rental parking lots in the Multi-Modal Facility located next to the Economy Parking lot.

  • What can I do at Philadelphia Airport before the flight?

    As you wait for your flight departure at Philadelphia Airport, check out the on-site Art Exhibitions at various terminals in the airport. You can find art displays in Terminals A-East, B, C, and D with impressive displays that humanize the airport's surroundings.

  • Are there non-stop flights to Chicago from Philadelphia Airport?

    American and United are two major airlines that provide non-stop flights from Philadelphia to Chicago. However, most flights serving the route have one stop. Spirit Airlines, Frontier Airlines, Delta Air Lines, and Sun Country Airlines all have a single flight layover in Miramar, Denver, Atlanta, and Minneapolis, respectively.

  • Which is the fastest transport option to the city center from Chicago O'Hare Airport?

    Taking a taxi to Downtown Chicago is a quicker means of ground transportation from O'Hare Airport. Taxi operators are located outside the airport terminal, ready to take you to the city for about $50. The journey takes about 35min and might vary depending on the traffic. You can opt for the Blue Line L train that takes an average of 45min to get to the city center. Alternatively, you can use GO Airport Express that offers nonstop shared ride services, which may take a few more extra minutes, as you might have to wait for other passengers.

  • 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 $35 for a one-way ticket and $73 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, and Delta 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Philadelphia and Chicago, with oneworld 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 $302 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 $152 or less one-way and $195 or less round-trip.
  • An advantage of flying from Philadelphia International Airport (PHL) is that it lies about 7 miles from the downtown area and gives you hassle-free access to the city. Make sure to board your plane to Chicago at the right terminal for quick and convenient security screenings and take-offs. Delta Air Lines and Sun Country Airlines generally depart from Terminal D, while Spirit Airlines and Frontier Airlines depart from Terminal E.
  • Art enthusiasts will love touching down at Chicago O'Hare Airport (ORD). Before leaving the airport, check out The Sky's the Limit Sculpture in Terminal 1 or the Palimpsest, a beautiful tapestry construction made using shoelaces and nylon fishing nets, located in the airport's Multi-Modal Facility.
  • If you'd rather get accommodation at the airport instead of going to Downtown Chicago, we recommend booking a flight to Chicago O'Hare Airport. The Hilton Hotel lies right at the airport, opposite Terminals 1, 2, and 3. It offers convenient flight boarding and take-offs.
  • For nursing facilities, there are Mamava mobile pods, situated in Terminal A-West, Terminal F, and the B/C Connector. Alternatively, go to Minute Suites private room, between Terminals B and A-East, where you can nurse privately for free for the first 30min.
  • Traveling on a budget? You can get cheaper can easier access to Philadelphia Airport from the city center using the SEPTA Airport Line Regional Rail trains. These trains travel the route at 30min intervals. The fare will cost around $7-$8, and the journey takes about 30min.

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 4244 reviews
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

Southwest's seats are the least comfortable I have ever sat in.

4.0 OkayDavid, Aug 2025DTW - STL
Read more Southwest reviews

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.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

Flight attendant moved my bag without notifying me and was rude to me when I asked him about it. There was no reason to move it.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Plane was delayed for 6 hours, at first by weather, which is understandable, but was further delayed with NO given reason for 2 1/2 hours more. We had no clue when we were going to depart actually until they opened the ramp. VERY POOR to ZERO COMMUNICATION!!!

Flight was delayed and after being in the airport for like seven hours, it was canceled.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

We started with trouble checking in 24 hours early. Then my husband did not get his TSA precheck. Finally flight delayed due to no crew. I know things happen

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

It’s a great flight. Service is good. Staff is awesome.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

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

Information on your arrival and departure airports

Compare transportation modes for Philadelphia to Chicago

Transportation modeAverage priceAverage duration
Flights$7112h 05m
Trains$32426h 45m

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