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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 4/8. 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 from Philadelphia to Chicago

The cheapest plane tickets from Philadelphia to Chicago found on KAYAK recently.
6:40 am - 12:21 amPHL-MDW
18h 41m1 stop
2:36 pm - 5:36 pmMDW-PHL
2h 00mnonstop
$96Frontier
Find Deal
mar., abr. 1 - mar., abr. 8
5:30 am - 11:26 amPHL-ORD
6h 56m1 stop
10:55 am - 12:30 amORD-PHL
12h 35m1 stop
$109Frontier
Find Deal
jue., abr. 24 - lun., abr. 28
12:50 pm - 2:14 pmPHL-ORD
2h 24mnonstop
7:30 am - 10:38 amORD-PHL
2h 08mnonstop
$177United Airlines
Find Deal
mié., abr. 16 - mié., abr. 23
10:30 am - 12:02 pmPHL-ORD
2h 32mnonstop
11:53 am - 2:55 pmORD-PHL
2h 02mnonstop
$187American Airlines
Find Deal
jue., abr. 3 - mar., abr. 8
6:30 am - 8:01 amPHL-ORD
2h 31mnonstop
2:25 pm - 5:25 pmORD-PHL
2h 00mnonstop
$197United Airlines
Find Deal
jue., feb. 13 - jue., feb. 13
5:02 pm - 10:29 pmPHL-MDW
6h 27m1 stop
5:59 pm - 11:01 pmMDW-PHL
4h 02m1 stop
$197Delta
Find Deal
mié., abr. 16 - mar., abr. 22
9:15 pm - 10:44 pmPHL-ORD
2h 29mnonstop
6:30 am - 9:29 amORD-PHL
1h 59mnonstop
$198American Airlines
Find Deal
jue., feb. 20 - lun., feb. 24
5:00 am - 9:50 amPHL-MDW
5h 50m1 stop
8:35 am - 11:30 amMDW-PHL
1h 55mnonstop
$205Southwest
Find Deal
mar., feb. 18 - jue., feb. 20
5:45 am - 2:10 pmPHL-MDW
9h 25m1 stop
1:00 pm - 3:50 pmMDW-PHL
1h 50mnonstop
$207Southwest
Find Deal
jue., feb. 20 - lun., feb. 24
6:00 am - 12:42 pmPHL-MDW
7h 42m1 stop
9:33 am - 4:05 pmMDW-PHL
5h 32m1 stop
$214Delta
Find Deal
mar., feb. 18 - jue., feb. 20
6:31 pm - 7:51 pmPHL-MDW
2h 20mnonstop
$28Frontier
Find Deal
mar., abr. 8
6:31 pm - 7:51 pmPHL-MDW
2h 20mnonstop
$29Frontier
Find Deal
mar., abr. 8
9:31 am - 10:55 amPHL-ORD
2h 24mnonstop
$89United Airlines
Find Deal
mié., abr. 2
6:25 am - 7:40 amPHL-MDW
2h 15mnonstop
$89Southwest
Find Deal
mar., abr. 1
10:10 am - 11:41 amPHL-ORD
2h 31mnonstop
$99United Airlines
Find Deal
lun., feb. 24
6:00 am - 7:15 amPHL-MDW
2h 15mnonstop
$99Southwest
Find Deal
lun., mar. 17
9:15 pm - 10:47 pmPHL-ORD
2h 32mnonstop
$100American Airlines
Find Deal
lun., mar. 17
11:37 am - 5:43 pmPHL-MDW
7h 06m1 stop
$109Delta
Find Deal
jue., feb. 20
5:40 am - 9:42 amPHL-ORD
5h 02m1 stop
$129Delta
Find Deal
vie., feb. 21
9:02 am - 12:04 pmPHL-ORD
4h 02m1 stop
$179American Airlines
Find Deal
jue., mar. 27
7:20 am - 4:23 pmPHL-ORD
10h 03m1 stop
6:55 am - 6:55 pmORD-PHL
11h 00m1 stop
lun., ene. 27 - jue., ene. 30
7:20 am - 4:23 pmPHL-ORD
10h 03m1 stop
6:55 am - 6:55 pmORD-PHL
11h 00m1 stop
lun., ene. 27 - jue., ene. 30
3:52 pm - 11:33 pmPHL-ORD
8h 41m1 stop
8:38 am - 7:26 pmORD-PHL
9h 48m1 stop
$299Frontier
Find Deal
vie., ene. 24 - lun., ene. 27
10:18 pm - 9:52 amPHL-ORD
12h 34m1 stop
3:16 pm - 11:58 pmORD-PHL
7h 42m1 stop
$309Frontier
Find Deal
sáb., ene. 25 - lun., ene. 27
2:46 pm - 11:46 amPHL-ORD
22h 00m2 stops
2:29 pm - 5:35 pmORD-PHL
2h 06mnonstop
$404United Airlines
Find Deal
vie., ene. 24 - sáb., ene. 25
10:35 am - 8:03 amPHL-ORD
22h 28m2 stops
11:20 am - 2:24 pmORD-PHL
2h 04mnonstop
$485United Airlines
Find Deal
vie., ene. 24 - sáb., ene. 25
9:28 am - 2:06 pmPHL-ORD
5h 38m1 stop
5:20 pm - 8:19 pmORD-PHL
1h 59mnonstop
$720American Airlines
Find Deal
sáb., ene. 25 - sáb., ene. 25
6:00 am - 7:20 amPHL-MDW
2h 20mnonstop
6:15 pm - 9:05 pmMDW-PHL
1h 50mnonstop
$755Southwest
Find Deal
mar., ene. 28 - mar., feb. 4
3:30 pm - 7:25 pmPHL-MDW
4h 55m1 stop
10:05 am - 1:00 pmMDW-PHL
1h 55mnonstop
$765Southwest
Find Deal
mar., ene. 28 - jue., ene. 30
7:20 am - 8:45 amPHL-ORD
2h 25mnonstop
12:20 pm - 5:07 pmORD-PHL
3h 47m1 stop
$842American Airlines
Find Deal
lun., ene. 27 - lun., ene. 27
6:31 pm - 7:51 pmPHL-MDW
2h 20mnonstop
4:25 pm - 7:23 pmMDW-PHL
1h 58mnonstop
$109Frontier
Find Deal
mar., abr. 8 - dom., abr. 13
8:23 pm - 9:40 pmPHL-MDW
2h 17mnonstop
2:36 pm - 5:36 pmMDW-PHL
2h 00mnonstop
$123Frontier
Find Deal
jue., abr. 3 - mar., abr. 8
6:31 pm - 7:51 pmPHL-MDW
2h 20mnonstop
2:36 pm - 5:36 pmMDW-PHL
2h 00mnonstop
$124Frontier
Find Deal
mar., abr. 1 - mar., abr. 8
4:12 pm - 5:28 pmPHL-MDW
2h 16mnonstop
12:15 pm - 3:17 pmMDW-PHL
2h 02mnonstop
$134Frontier
Find Deal
vie., may. 9 - lun., may. 12
12:50 pm - 2:14 pmPHL-ORD
2h 24mnonstop
7:30 am - 10:38 amORD-PHL
2h 08mnonstop
$177United Airlines
Find Deal
mié., abr. 16 - mié., abr. 23
10:30 am - 12:02 pmPHL-ORD
2h 32mnonstop
11:53 am - 2:55 pmORD-PHL
2h 02mnonstop
$187American Airlines
Find Deal
jue., abr. 3 - mar., abr. 8
6:35 pm - 7:45 pmPHL-MDW
2h 10mnonstop
5:50 am - 8:45 amMDW-PHL
1h 55mnonstop
$187Southwest
Find Deal
mié., abr. 16 - lun., abr. 21
1:00 pm - 2:32 pmPHL-ORD
2h 32mnonstop
7:25 am - 10:28 amORD-PHL
2h 03mnonstop
$197United Airlines
Find Deal
mié., feb. 26 - lun., mar. 3
6:15 am - 7:45 amPHL-MDW
2h 30mnonstop
8:35 am - 11:30 amMDW-PHL
1h 55mnonstop
$197Southwest
Find Deal
jue., feb. 20 - lun., feb. 24
9:15 pm - 10:44 pmPHL-ORD
2h 29mnonstop
6:30 am - 9:29 amORD-PHL
1h 59mnonstop
$198American Airlines
Find Deal
jue., feb. 20 - lun., feb. 24

United Airlines flights from Philadelphia to Chicago

Our best United Airlines deals on Philadelphia to Chicago flight tickets
United Airlines
Apr 16
PHL12:50 pmPhiladelphia
2h 24m
ORD2:14 pmChicago O'Hare Intl
Apr 23
ORD7:30 amChicago O'Hare Intl
2h 08m
PHL10:38 amPhiladelphia
United Airlines
Feb 13
PHL6:30 amPhiladelphia
2h 31m
ORD8:01 amChicago O'Hare Intl
Feb 13
ORD2:25 pmChicago O'Hare Intl
2h 00m
PHL5:25 pmPhiladelphia
United Airlines
Feb 20
PHL6:00 amPhiladelphia
4h 48m
1 stop
ORD9:48 amChicago O'Hare Intl
Feb 27
ORD11:15 amChicago O'Hare Intl
2h 00m
PHL2:15 pmPhiladelphia

Frontier flights from Philadelphia to Chicago

Our best Frontier deals on Philadelphia to Chicago flight tickets
Frontier
Apr 1
PHL6:40 amPhiladelphia
18h 41m
1 stop
MDW12:21 amChicago Midway
Apr 8
MDW2:36 pmChicago Midway
2h 00m
PHL5:36 pmPhiladelphia
Frontier
Apr 24
PHL5:30 amPhiladelphia
6h 56m
1 stop
ORD11:26 amChicago O'Hare Intl
Apr 28
ORD10:55 amChicago O'Hare Intl
12h 35m
1 stop
PHL12:30 amPhiladelphia
Frontier
Feb 10
PHL4:42 pmPhiladelphia
6h 45m
1 stop
ORD10:27 pmChicago O'Hare Intl
Feb 19
ORD8:33 amChicago O'Hare Intl
6h 38m
1 stop
PHL4:11 pmPhiladelphia

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 typical price of a round-trip flight between Philadelphia and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Philadelphia, with most prices found around $118. If you’re not able to fly to Chicago in September, then July is your next best option. Flight prices from Philadelphia to Chicago during July average around $161.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $273. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Philadelphia to Chicago for around $395.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Philadelphia to Chicago during this time can be as low as $168. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $351.

What is the cheapest Philadelphia to Chicago flight route?

Fly from Philadelphia to Chicago O'Hare Intl for the best Philadelphia - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Philadelphia when booking 14 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $246 when searching 14 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Philadelphia for as low as $183 on momondo.

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.

How have Philadelphia to Chicago flight prices changed over time?

As of January 2025, prices for Philadelphia to Chicago flights are approximately 22% 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 05m

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 $96.
The fastest flight from Philadelphia to Chicago takes 2h 05m
Direct flights go from Philadelphia to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • Is flying the fastest way to get from Philadelphia to Chicago?

    We’ve found that taking a flight from Philadelphia to Chicago with Frontier is more time-efficient when based simply on travel duration. A train from Philadelphia to Chicago or a bus from Philadelphia to Chicago can take you longer than a 2h 14m flight.

  • Is flying the cheapest way to get from Philadelphia to Chicago?

    Taking a flight to your destination is the cheapest option we’ve found in the past few days. The cheapest price we’ve found for this option is $96, making it less expensive than a train from Philadelphia to Chicago and cheaper than a bus from Philadelphia to Chicago.

  • How far is Philadelphia to Chicago by plane?

    A flight from Philadelphia to Chicago will travel around 663.6 mi. 2h 14m 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
6.0
3,440 reviews
Search Frontier flights
American AirlinesPriceFrom $131Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $139Free CancellationRating
7.4
8,970 reviews
Search United Airlines flights
SouthwestPriceFrom $150Free CancellationRating
8.1
4,647 reviews
Search Southwest flights
DeltaPriceFrom $186Free CancellationRating
8.0
8,508 reviews
Search Delta flights
  • Southwest Flights From Philadelphia to Chicago

    Southwest is one of the most popular airlines flying from Philadelphia to Chicago, operating 21 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 $248. 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 $139 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $286. United Airlines operates 14 flights to Chicago from Philadelphia in an average week. Users have rated it 7.4/10 across 8,970 reviews.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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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