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Cheap flights from Philadelphia to Chicago from $39

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 4/1. 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.
7:38 pm - 9:04 pmPHL-MDW
2h 26mnonstop
7:30 am - 6:21 pmMDW-PHL
9h 51m1 stop
$101Frontier
Find Deal
lun., ene. 6 - jue., ene. 9
7:30 am - 4:31 pmPHL-ORD
10h 01m1 stop
7:59 pm - 7:38 amORD-PHL
10h 39m1 stop
$108Frontier
Find Deal
mié., feb. 12 - sáb., feb. 15
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
6:15 pm - 9:05 pmMDW-PHL
1h 50mnonstop
$175Southwest
Find Deal
mié., ene. 29 - mié., ene. 29
10:10 am - 11:41 amPHL-ORD
2h 31mnonstop
6:30 pm - 9:40 pmORD-PHL
2h 10mnonstop
$181United Airlines
Find Deal
mié., ene. 22 - mié., ene. 29
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
12:25 pm - 3:15 pmMDW-PHL
1h 50mnonstop
$181Southwest
Find Deal
mié., ene. 22 - mié., ene. 29
10:41 am - 12:12 pmPHL-ORD
2h 31mnonstop
5:20 pm - 8:19 pmORD-PHL
1h 59mnonstop
$182American Airlines
Find Deal
mié., feb. 5 - mié., feb. 12
9:33 am - 1:08 pmPHL-MDW
4h 35m1 stop
5:07 pm - 10:52 pmMDW-PHL
4h 45m1 stop
$196Delta
Find Deal
mar., ene. 21 - mar., ene. 28
1:00 pm - 4:13 pmPHL-ORD
4h 13m1 stop
10:30 am - 3:55 pmORD-PHL
4h 25m1 stop
$200Delta
Find Deal
mar., ene. 7 - mié., ene. 15
9:25 am - 10:51 amPHL-ORD
2h 26mnonstop
5:20 pm - 8:19 pmORD-PHL
1h 59mnonstop
$201American Airlines
Find Deal
mié., ene. 8 - lun., ene. 13
6:15 am - 9:44 amPHL-ORD
4h 29m1 stop
2:29 pm - 5:35 pmORD-PHL
2h 06mnonstop
$204United Airlines
Find Deal
mié., ene. 29 - mié., ene. 29
6:31 pm - 7:51 pmPHL-MDW
2h 20mnonstop
$39Frontier
Find Deal
mar., abr. 1
4:42 pm - 10:27 pmPHL-ORD
6h 45m1 stop
$54Frontier
Find Deal
jue., ene. 23
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
$91Southwest
Find Deal
mié., ene. 22
1:37 pm - 3:04 pmPHL-ORD
2h 27mnonstop
$92American Airlines
Find Deal
mié., ene. 22
9:33 am - 1:05 pmPHL-MDW
4h 32m1 stop
$98Delta
Find Deal
mié., feb. 26
6:00 am - 12:46 pmPHL-MDW
7h 46m1 stop
$100Delta
Find Deal
mié., ene. 22
6:00 am - 7:31 amPHL-ORD
2h 31mnonstop
$111United Airlines
Find Deal
jue., ene. 23
1:30 pm - 2:45 pmPHL-MDW
2h 15mnonstop
$111Southwest
Find Deal
lun., feb. 24
10:10 am - 11:41 amPHL-ORD
2h 31mnonstop
$126United Airlines
Find Deal
mar., ene. 21
10:41 am - 12:12 pmPHL-ORD
2h 31mnonstop
$157American Airlines
Find Deal
vie., feb. 7
10:26 pm - 10:19 amPHL-ORD
12h 53m1 stop
10:35 am - 7:02 pmORD-PHL
7h 27m1 stop
$202Frontier
Find Deal
sáb., dic. 28 - jue., ene. 9
5:15 am - 6:39 amPHL-MDW
2h 24mnonstop
9:59 pm - 12:58 amMDW-PHL
1h 59mnonstop
$218Frontier
Find Deal
jue., dic. 26 - lun., ene. 6
6:35 am - 8:05 amPHL-ORD
2h 30mnonstop
11:20 am - 2:24 pmORD-PHL
2h 04mnonstop
$539United Airlines
Find Deal
jue., dic. 26 - mié., ene. 8
6:00 am - 9:21 amPHL-ORD
4h 21m1 stop
6:45 am - 12:10 pmORD-PHL
4h 25m1 stop
$558Delta
Find Deal
mié., dic. 25 - sáb., ene. 11
11:00 am - 4:17 pmPHL-MDW
6h 17m1 stop
5:07 pm - 10:52 pmMDW-PHL
4h 45m1 stop
$558Delta
Find Deal
jue., dic. 26 - mar., ene. 14
6:35 am - 8:05 amPHL-ORD
2h 30mnonstop
11:20 am - 2:24 pmORD-PHL
2h 04mnonstop
$559United Airlines
Find Deal
sáb., dic. 28 - sáb., ene. 11
3:40 pm - 7:06 pmPHL-ORD
4h 26m1 stop
11:51 am - 2:55 pmORD-PHL
2h 04mnonstop
$569American Airlines
Find Deal
sáb., dic. 28 - sáb., ene. 11
7:35 am - 8:45 amPHL-MDW
2h 10mnonstop
6:15 pm - 9:05 pmMDW-PHL
1h 50mnonstop
$570Southwest
Find Deal
mar., dic. 24 - vie., ene. 31
12:00 pm - 9:30 pmPHL-ORD
10h 30m2 stops
11:25 am - 9:45 pmORD-PHL
9h 20m1 stop
$595Southwest
Find Deal
mié., dic. 25 - mar., dic. 31
1:40 pm - 3:08 pmPHL-ORD
2h 28mnonstop
6:35 pm - 9:57 pmORD-PHL
2h 22mnonstop
$724American Airlines
Find Deal
vie., dic. 27 - dom., dic. 29
8:23 pm - 9:40 pmPHL-MDW
2h 17mnonstop
4:30 pm - 7:28 pmMDW-PHL
1h 58mnonstop
$139Frontier
Find Deal
jue., abr. 3 - dom., abr. 6
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
6:15 pm - 9:05 pmMDW-PHL
1h 50mnonstop
$175Southwest
Find Deal
mié., ene. 29 - mié., ene. 29
10:10 am - 11:41 amPHL-ORD
2h 31mnonstop
6:30 pm - 9:40 pmORD-PHL
2h 10mnonstop
$181United Airlines
Find Deal
mié., ene. 22 - mié., ene. 29
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
12:25 pm - 3:15 pmMDW-PHL
1h 50mnonstop
$181Southwest
Find Deal
mié., ene. 22 - mié., ene. 29
6:00 am - 7:31 amPHL-ORD
2h 31mnonstop
7:45 am - 10:50 amORD-PHL
2h 05mnonstop
$201United Airlines
Find Deal
jue., ene. 9 - mar., ene. 14
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
8:00 am - 10:55 amMDW-PHL
1h 55mnonstop
$201Southwest
Find Deal
mar., feb. 25 - jue., feb. 27
1:44 pm - 3:06 pmPHL-MDW
2h 22mnonstop
9:59 pm - 12:58 amMDW-PHL
1h 59mnonstop
$219Frontier
Find Deal
vie., ene. 3 - lun., ene. 6
6:35 pm - 8:08 pmPHL-ORD
2h 33mnonstop
5:18 pm - 8:12 pmORD-PHL
1h 54mnonstop
$247American Airlines
Find Deal
vie., feb. 21 - mar., feb. 25
10:50 am - 12:21 pmPHL-ORD
2h 31mnonstop
9:45 am - 12:42 pmORD-PHL
1h 57mnonstop
$267American Airlines
Find Deal
vie., feb. 21 - sáb., feb. 22
7:52 pm - 9:20 pmPHL-ORD
2h 28mnonstop
7:53 pm - 10:53 pmORD-PHL
2h 00mnonstop
jue., ene. 2 - mié., ene. 8

American Airlines flights from Philadelphia to Chicago

Our best American Airlines deals on Philadelphia to Chicago flight tickets
American Airlines
Feb 5
PHL10:41 amPhiladelphia
2h 31m
ORD12:12 pmChicago O'Hare Intl
Feb 12
ORD5:20 pmChicago O'Hare Intl
1h 59m
PHL8:19 pmPhiladelphia
American Airlines
Jan 8
PHL9:25 amPhiladelphia
2h 26m
ORD10:51 amChicago O'Hare Intl
Jan 13
ORD5:20 pmChicago O'Hare Intl
1h 59m
PHL8:19 pmPhiladelphia
American Airlines
Jan 22
PHL3:55 pmPhiladelphia
2h 29m
ORD5:24 pmChicago O'Hare Intl
Jan 29
ORD12:20 pmChicago O'Hare Intl
3h 47m
1 stop
PHL5:07 pmPhiladelphia

Spirit Airlines flights from Philadelphia to Chicago

Our best Spirit Airlines deals on Philadelphia to Chicago flight tickets
Spirit Airlines
May 3
PHL3:30 pmPhiladelphia
7h 51m
1 stop
ORD10:21 pmChicago O'Hare Intl
May 4
ORD6:15 amChicago O'Hare Intl
25h 05m
1 stop
PHL8:20 amPhiladelphia
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
16h 20m
1 stop
PHL11:35 pmPhiladelphia
Spirit Airlines
May 1
PHL8:50 pmPhiladelphia
26h 31m
1 stop
ORD10:21 pmChicago O'Hare Intl
May 5
ORD6:15 amChicago O'Hare Intl
7h 25m
1 stop
PHL2:40 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 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 Tuesday when prices can be found for as low as $156. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Philadelphia to Chicago for around $199.

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 $148. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $217.

What is the cheapest Philadelphia to Chicago flight route?

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

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

The best time to book a flight to Chicago from Philadelphia is 41 days out, which is when prices tend to be around $245. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $171.

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?

You could potentially save up to 35% on your flight if you consider stops on a Philadelphia to Chicago flight.

How have Philadelphia to Chicago flight prices changed over time?

As of December 2024, prices for Philadelphia to Chicago flights are approximately 33% 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

$39

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 $39. The best round-trip flight deal from Philadelphia to Chicago found on momondo in the last 72 hours is $101.
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 Southwest 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 05m 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 $101, 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 05m 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
3,469 reviews
Search Frontier flights
American AirlinesPriceFrom $132Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $140Free CancellationRating
7.4
9,020 reviews
Search United Airlines flights
SouthwestPriceFrom $150Free CancellationRating
8.1
4,780 reviews
Search Southwest flights
DeltaPriceFrom $157Free CancellationRating
8.0
8,588 reviews
Search Delta flights
  • Southwest Flights From Philadelphia to Chicago

    Southwest is one of the most popular airlines flying from Philadelphia to Chicago, operating 20 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 $238. 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 $140 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $286. United Airlines operates 13 flights to Chicago from Philadelphia in an average week. Users have rated it 7.4/10 across 9,020 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.


Choose the best way to get from Philadelphia to Chicago

Buses

20h 05m
$105 one-way$270 round-trip
Nonstop · from $270

Distance to downtown

F990.8 mi

Find Buses

Philadelphia to Chicago Buses

Trains

26h 45m
$99 one-way$285 round-trip
Nonstop · from $285

Distance to downtown

ZUN0.7 mi

Flights

2h 10m
$39 one-way$101 round-trip
1 stop · from $101

Distance to downtown

ORD15.9 mi
MDW8.6 mi

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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago