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Cheap flights from Philadelphia to Chicago from $28

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Philadelphia to Chicago departing on 12/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Philadelphia to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Philadelphia to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Philadelphia to Chicago.

Cheap last minute flights

Planning a quick getaway from Philadelphia to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Philadelphia to Chicago

Find recent round-trip train or bus tickets from Philadelphia to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$58Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 24
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:34 am - 10:37 amMDW-PHL
2h 03mnonstop
$67Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 19
4:00 pm - 5:30 pmPHL-ORD
2h 30mnonstop
8:36 pm - 11:42 pmORD-PHL
2h 06mnonstop
$132American Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 15
7:20 am - 8:45 amPHL-ORD
2h 25mnonstop
11:53 am - 2:54 pmORD-PHL
2h 01mnonstop
$137American Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
6:30 am - 7:54 amPHL-ORD
2h 24mnonstop
11:20 am - 2:20 pmORD-PHL
2h 00mnonstop
$171United Airlines
Find Deal
Mon, Dec 9 - Wed, Dec 11
7:35 am - 8:45 amPHL-MDW
2h 10mnonstop
6:15 pm - 9:05 pmMDW-PHL
1h 50mnonstop
$172Southwest
Find Deal
Thu, Dec 5 - Tue, Dec 10
5:15 pm - 6:39 pmPHL-ORD
2h 24mnonstop
2:30 pm - 5:36 pmORD-PHL
2h 06mnonstop
$174United Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 24
7:35 am - 8:45 amPHL-MDW
2h 10mnonstop
8:15 pm - 11:10 pmMDW-PHL
1h 55mnonstop
$185Southwest
Find Deal
Wed, Dec 11 - Fri, Dec 13
12:31 pm - 5:09 pmPHL-ORD
5h 38m1 stop
5:20 pm - 11:19 pmORD-PHL
4h 59m1 stop
$196Delta
Find Deal
Wed, Dec 4 - Sat, Dec 14
6:07 pm - 10:20 pmPHL-MDW
5h 13m1 stop
9:34 am - 3:55 pmMDW-PHL
5h 21m1 stop
$196Delta
Find Deal
Tue, Jan 14 - Thu, Jan 23
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
$28Frontier
Find Deal
Tue, Dec 17
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
$29Frontier
Find Deal
Tue, Dec 17
1:40 pm - 3:05 pmPHL-ORD
2h 25mnonstop
$69American Airlines
Find Deal
Tue, Feb 25
6:05 am - 7:30 amPHL-MDW
2h 25mnonstop
$69Southwest
Find Deal
Tue, Feb 25
7:21 am - 8:50 amPHL-ORD
2h 29mnonstop
$86American Airlines
Find Deal
Tue, Dec 17
7:35 am - 8:45 amPHL-MDW
2h 10mnonstop
$86Southwest
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Wed, Dec 11
4:38 pm - 6:10 pmPHL-ORD
2h 32mnonstop
$89United Airlines
Find Deal
Tue, Dec 31
6:00 am - 9:48 amPHL-ORD
4h 48m1 stop
$94United Airlines
Find Deal
Wed, Feb 19
5:30 am - 10:46 amPHL-ORD
6h 16m1 stop
$98Delta
Find Deal
Sat, Dec 7
6:00 am - 1:31 pmPHL-MDW
8h 31m1 stop
$98Delta
Find Deal
Wed, Dec 11
6:18 pm - 7:44 pmPHL-ORD
2h 26mnonstop
8:01 pm - 11:07 pmORD-PHL
2h 06mnonstop
$137Frontier
Find Deal
Sun, Nov 24 - Wed, Nov 27
6:18 pm - 7:44 pmPHL-ORD
2h 26mnonstop
8:51 am - 11:57 amORD-PHL
2h 06mnonstop
$154Frontier
Find Deal
Sun, Nov 24 - Tue, Nov 26
6:18 pm - 7:44 pmPHL-ORD
2h 26mnonstop
11:51 am - 1:17 amORD-PHL
12h 26m1 stop
Sun, Nov 24 - Mon, Nov 25
6:18 pm - 7:44 pmPHL-ORD
2h 26mnonstop
1:09 pm - 1:17 amORD-PHL
11h 08m1 stop
Sun, Nov 24 - Tue, Nov 26
6:11 am - 6:31 pmPHL-ORD
13h 20m1 stop
11:51 am - 1:17 amORD-PHL
12h 26m1 stop
$264Spirit Airlines
Find Deal
Sun, Nov 24 - Mon, Nov 25
7:00 am - 4:50 pmPHL-ORD
10h 50m1 stop
11:51 am - 1:17 amORD-PHL
12h 26m1 stop
$302Spirit Airlines
Find Deal
Sat, Nov 23 - Mon, Nov 25
5:15 am - 1:40 pmPHL-MDW
9h 25m2 stops
6:20 am - 1:55 pmMDW-PHL
6h 35m1 stop
$595Southwest
Find Deal
Sun, Nov 24 - Fri, Nov 29
4:35 pm - 11:45 pmPHL-MDW
8h 10m2 stops
8:00 am - 2:50 pmMDW-PHL
5h 50m1 stop
$596Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
6:00 am - 1:35 pmPHL-MDW
8h 35m2 stops
6:49 pm - 12:54 amMDW-PHL
5h 05m1 stop
$1,373Delta
Find Deal
Thu, Nov 21 - Thu, Nov 21
9:37 am - 6:32 pmPHL-MDW
9h 55m2 stops
1:30 pm - 7:36 pmMDW-PHL
5h 06m1 stop
$1,409Delta
Find Deal
Sat, Nov 23 - Sun, Nov 24
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$58Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 24
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:34 am - 10:37 amMDW-PHL
2h 03mnonstop
$67Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 19
9:10 pm - 10:38 pmPHL-ORD
2h 28mnonstop
10:22 pm - 1:29 amORD-PHL
2h 07mnonstop
$68Frontier
Find Deal
Mon, Dec 16 - Wed, Dec 18
4:00 pm - 5:30 pmPHL-ORD
2h 30mnonstop
8:36 pm - 11:42 pmORD-PHL
2h 06mnonstop
$132American Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 15
6:35 am - 8:05 amPHL-MDW
2h 30mnonstop
10:20 am - 1:15 pmMDW-PHL
1h 55mnonstop
$133Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 15
7:20 am - 8:45 amPHL-ORD
2h 25mnonstop
11:53 am - 2:54 pmORD-PHL
2h 01mnonstop
$137American Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
5:05 pm - 6:20 pmPHL-MDW
2h 15mnonstop
10:05 am - 1:00 pmMDW-PHL
1h 55mnonstop
$158Southwest
Find Deal
Sat, Jan 18 - Sun, Jan 19
9:10 pm - 10:38 pmPHL-ORD
2h 28mnonstop
2:26 pm - 5:29 pmORD-PHL
2h 03mnonstop
Mon, Dec 9 - Sat, Dec 14
6:30 am - 7:54 amPHL-ORD
2h 24mnonstop
2:26 pm - 5:29 pmORD-PHL
2h 03mnonstop
$171United Airlines
Find Deal
Mon, Dec 9 - Thu, Dec 12
5:15 pm - 6:39 pmPHL-ORD
2h 24mnonstop
2:30 pm - 5:36 pmORD-PHL
2h 06mnonstop
$174United Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 24

American Airlines flights from Philadelphia to Chicago

Our best American Airlines deals on Philadelphia to Chicago flight tickets
American Airlines
Feb 15
PHL4:00 pmPhiladelphia
2h 30m
ORD5:30 pmChicago O'Hare Intl
Feb 15
ORD8:36 pmChicago O'Hare Intl
2h 06m
PHL11:42 pmPhiladelphia
American Airlines
Jan 18
PHL7:20 amPhiladelphia
2h 25m
ORD8:45 amChicago O'Hare Intl
Jan 21
ORD11:53 amChicago O'Hare Intl
2h 01m
PHL2:54 pmPhiladelphia
American Airlines
Jan 17
PHL1:37 pmPhiladelphia
2h 27m
ORD3:04 pmChicago O'Hare Intl
Jan 21
ORD2:52 pmChicago O'Hare Intl
2h 03m
PHL5:55 pmPhiladelphia

Spirit Airlines flights from Philadelphia to Chicago

Our best Spirit Airlines deals on Philadelphia to Chicago flight tickets
Spirit Airlines
May 7
PHL6:00 amPhiladelphia
17h 21m
1 stop
ORD10:21 pmChicago O'Hare Intl
May 12
ORD6:15 amChicago O'Hare Intl
25h 05m
1 stop
PHL8:20 amPhiladelphia
Spirit Airlines
Dec 3
PHL9:18 pmPhiladelphia
14h 14m
2 stops
ORD10:32 amChicago O'Hare Intl
Dec 6
ORD5:11 pmChicago O'Hare Intl
13h 37m
2 stops
PHL7:48 amPhiladelphia
Spirit Airlines
Dec 5
PHL7:27 pmPhiladelphia
15h 50m
2 stops
ORD10:17 amChicago O'Hare Intl
Dec 10
ORD9:58 amChicago O'Hare Intl
20h 50m
2 stops
PHL7:48 amPhiladelphia

See travel insights to Chicago from

How to get the cheapest flight ticket from Philadelphia to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

September. The cheapest time of year to fly to Chicago from Philadelphia is September. Most expensive is February

What is the cheapest day to depart Philadelphia for Chicago?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Friday

When is the cheapest time to fly from Philadelphia to Chicago?

In the evening. Philadelphia to Chicago flights are approximately 35% more expensive at noon than in the evening

What is the cheapest Philadelphia to Chicago flight route?

Philadelphia - Chicago Midway. Fly from Philadelphia to Chicago Midway for the best Philadelphia - Chicago flight prices

How far in advance should you book Philadelphia to Chicago flights?

48 days before. The cheapest time to buy a flight from Philadelphia to Chicago is approximately 48 days to departure

What cabin class options are available on Philadelphia to Chicago flights?

There are 4 cabin classes available to choose from on Philadelphia to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Philadelphia to Chicago flights?

No. A direct flight is the cheapest option for a flight between Philadelphia to Chicago.

How have Philadelphia to Chicago flight prices changed over time?

As of November 2024, prices for Philadelphia to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

When to book flights from Philadelphia to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Philadelphia to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Philadelphia to Chicago (PHL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Philadelphia to Chicago

Best Price Found

$28

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Philadelphia in the past 72 hours is $28. The best round-trip flight deal from Philadelphia to Chicago found on momondo in the last 72 hours is $58.
The fastest flight from Philadelphia to Chicago takes 2h 10m
Direct flights go from Philadelphia to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Philadelphia to Chicago by plane?

    A flight from Philadelphia to Chicago will travel around 663.6 mi. 2h 10m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Philadelphia Airport to Chicago?

    Prices for flights from Philadelphia Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Philadelphia Airport to Chicago?

  • How old do you have to be to fly from Philadelphia Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Philadelphia Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Philadelphia to Chicago?

  • What is the most popular airline from Philadelphia to Chicago?


Best airlines flying from Philadelphia to Chicago

Compare and see reviews for airlines that fly from Philadelphia to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $48Free CancellationRating
6.1
3,539 reviews
Search Frontier flights
American AirlinesPriceFrom $132Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $142Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
SouthwestPriceFrom $150Free CancellationRating
8.1
5,014 reviews
Search Southwest flights
DeltaPriceFrom $157Free CancellationRating
8.0
8,756 reviews
Search Delta flights
  • Southwest Flights From Philadelphia to Chicago

    Southwest is one of the most popular airlines flying from Philadelphia to Chicago, operating 24 flights/week on average for this route. A good Southwest flight deal for Philadelphia to Chicago starts from $150 round-trip, up to an average price of $235. Our users have rated Southwest at 8.1/10.

  • United Airlines Flights From Philadelphia to Chicago

    United Airlines is also a popular choice for this route. United Airlines flight deals for Philadelphia to Chicago start from as low as $142 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $287. United Airlines operates 7 flights to Chicago from Philadelphia in an average week. Users have rated it 7.4/10 across 9,171 reviews.


Why use momondo?

Why should I use momondo to find a flight deal from Philadelphia to Chicago?

It is quick and easy to find Philadelphia to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Philadelphia to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Philadelphia with this policy.

How can momondo help me find flights from Philadelphia to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Philadelphia. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Philadelphia to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Philadelphia. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago