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Cheap flights from Philadelphia to Chicago from $71

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 12/3. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
2:35 pm - 11:28 pmPHL-ORD
9h 53m1 stop
Frontier Logo
3:18 pm - 12:19 amORD-PHL
8h 01m1 stop
$108Frontier
Find Deal
Mon, Nov 3 - Thu, Nov 6
Frontier Logo
6:50 pm - 9:12 amPHL-MDW
15h 22m1 stop
Frontier Logo
1:37 pm - 12:13 amMDW-PHL
9h 36m1 stop
$108Frontier
Find Deal
Wed, Oct 29 - Sat, Nov 1
Frontier Logo
6:42 am - 12:59 amPHL-ORD
19h 17m1 stop
Frontier Logo
11:53 am - 12:39 amORD-PHL
11h 46m1 stop
$109Frontier
Find Deal
Mon, Oct 27 - Mon, Nov 3
Frontier Logo
11:18 am - 2:22 pmPHL-MDW
28h 04m1 stop
Frontier Logo
11:36 am - 8:30 amMDW-PHL
19h 54m1 stop
$109Frontier
Find Deal
Thu, Oct 30 - Sat, Nov 1
Multiple Airlines Logo
3:10 pm - 12:41 pmPHL-MDW
22h 31m2 stops
Multiple Airlines Logo
9:15 am - 12:19 pmMDW-PHL
2h 04mnonstop
$123Multiple Airlines
Find Deal
Tue, Nov 11 - Mon, Nov 17
Multiple Airlines Logo
6:00 am - 7:26 amPHL-ORD
2h 26mnonstop
Multiple Airlines Logo
10:52 am - 11:26 pmORD-PHL
11h 34m1 stop
$134Multiple Airlines
Find Deal
Mon, Nov 3 - Tue, Nov 4
American Airlines Logo
7:35 am - 9:02 amPHL-ORD
2h 27mnonstop
American Airlines Logo
6:35 pm - 9:42 pmORD-PHL
2h 07mnonstop
$139American Airlines
Find Deal
Wed, Dec 3 - Sat, Dec 6
Southwest Logo
6:00 am - 7:15 amPHL-MDW
2h 15mnonstop
Southwest Logo
2:25 pm - 5:15 pmMDW-PHL
1h 50mnonstop
$139Southwest
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Wed, Nov 12 - Wed, Nov 19
Spirit Airlines Logo
5:00 pm - 11:34 pmPHL-ORD
7h 34m1 stop
Spirit Airlines Logo
3:21 pm - 11:16 pmORD-PHL
6h 55m1 stop
$156Spirit Airlines
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Wed, Dec 10 - Sun, Dec 14
Southwest Logo
4:00 pm - 5:10 pmPHL-MDW
2h 10mnonstop
Southwest Logo
1:00 pm - 3:55 pmMDW-PHL
1h 55mnonstop
$159Southwest
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Wed, Nov 5 - Sat, Nov 8

Frontier flights from Philadelphia to Chicago

Our best Frontier deals on Philadelphia to Chicago flight tickets
Frontier
Oct 25
PHL7:10 pmPhiladelphia
2h 38m
ORD8:48 pmChicago O'Hare Intl
Oct 27
ORD11:51 amChicago O'Hare Intl
2h 09m
PHL3:00 pmPhiladelphia
$108
Find similar
Frontier
Oct 27
PHL6:42 amPhiladelphia
19h 17m
1 stop
ORD12:59 amChicago O'Hare Intl
Nov 3
ORD11:53 amChicago O'Hare Intl
11h 46m
1 stop
PHL12:39 amPhiladelphia
$109
Find similar
Frontier
Nov 3
PHL5:50 amPhiladelphia
5h 51m
1 stop
ORD10:41 amChicago O'Hare Intl
Nov 6
ORD3:18 pmChicago O'Hare Intl
8h 01m
1 stop
PHL12:19 amPhiladelphia
$110
Find similar

Southwest flights from Philadelphia to Chicago

Our best Southwest deals on Philadelphia to Chicago flight tickets
Southwest
Nov 12
PHL6:00 amPhiladelphia
2h 15m
MDW7:15 amChicago Midway
Nov 19
MDW2:25 pmChicago Midway
1h 50m
PHL5:15 pmPhiladelphia
$139
Find similar
Southwest
Nov 5
PHL4:00 pmPhiladelphia
2h 10m
MDW5:10 pmChicago Midway
Nov 8
MDW1:00 pmChicago Midway
1h 55m
PHL3:55 pmPhiladelphia
$159
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Philadelphia to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 14, 2025.
Use the filters below to find and compare flights from Philadelphia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 11/3

2:35 pm-11:28 pm

1 stop9h 53m

Chicago O'Hare Intl

Thu 11/6

3:18 pm-12:19 am

1 stop8h 01m

$108

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/29

6:50 pm-9:12 am

1 stop15h 22m

Chicago Midway

Sat 11/1

1:37 pm-12:13 am

1 stop9h 36m

$108

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 10/27

6:42 am-12:59 am

1 stop19h 17m

Chicago O'Hare Intl

Mon 11/3

11:53 am-12:39 am

1 stop11h 46m

$109

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 10/30

11:18 am-2:22 pm

1 stop28h 04m

Chicago Midway

Sat 11/1

11:36 am-8:30 am

1 stop19h 54m

$109

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 11/11

3:10 pm-12:41 pm

2 stops22h 31m

Chicago Midway

Mon 11/17

9:15 am-12:19 pm

Nonstop2h 04m

$123

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 11/3

6:00 am-7:26 am

Nonstop2h 26m

Chicago O'Hare Intl

Tue 11/4

10:52 am-11:26 pm

1 stop11h 34m

$134

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 12/3

7:35 am-9:02 am

Nonstop2h 27m

Chicago O'Hare Intl

Sat 12/6

6:35 pm-9:42 pm

Nonstop2h 07m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 11/12

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Wed 11/19

2:25 pm-5:15 pm

Nonstop1h 50m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 12/10

5:00 pm-11:34 pm

1 stop7h 34m

Chicago O'Hare Intl

Sun 12/14

3:21 pm-11:16 pm

1 stop6h 55m

$156

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 11/5

4:00 pm-5:10 pm

Nonstop2h 10m

Chicago Midway

Sat 11/8

1:00 pm-3:55 pm

Nonstop1h 55m

$159

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $193. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from Philadelphia to Chicago during November average around $205.

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 Friday when prices can be found for as low as $329. 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 $474.

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 $259. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $405.

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?

You are more likely to see cheaper flights to Chicago from Philadelphia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $288 when searching 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 $215 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.

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 October 2025, prices for Philadelphia to Chicago flights are approximately 29% 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

$109

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Philadelphia in the past 72 hours is $109. The best round-trip flight deal from Philadelphia to Chicago found on momondo in the last 72 hours is $160.
The fastest flight from Philadelphia to Chicago takes 2h 05m
Direct flights go from Philadelphia to Chicago every day.
There is 1 airport near Chicago: Chicago Midway (MDW)
Search flight deals

  • 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 $62Free CancellationRating
5.8
3,135 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $83Free CancellationRating
6.3
8,096 reviews
Search Spirit Airlines flights
DeltaPriceFrom $118Free CancellationRating
7.9
7,975 reviews
Search Delta flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
8,976 reviews
Search United Airlines flights
SouthwestPriceFrom $165Free CancellationRating
8.0
4,238 reviews
Search Southwest flights
American AirlinesPriceFrom $166Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights

  • Southwest Flights From Philadelphia to Chicago

    Southwest is one of the most popular airlines flying from Philadelphia to Chicago, operating 23 flights/week on average for this route. A good Southwest flight deal for Philadelphia to Chicago starts from $165 round-trip, up to an average price of $307. Our users have rated Southwest at 8.0/10.

  • 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 $157 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $369. United Airlines operates 29 flights to Chicago from Philadelphia in an average week. Users have rated it 7.4/10 across 8,976 reviews.

Traveling to a place near Chicago?

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

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport