Are there direct flights from Philadelphia to Chicago?

Yes, direct flights are available from Philadelphia to Chicago. Historically, approximately 22.7% of all flights on this route have been direct. For journeys involving connecting flights, the median number of stopovers observed across the trailing 90 days was 2. Travelers can consider both direct and connecting options based on their preferences for travel time and convenience.

What's the flight time from Philadelphia to Chicago?

The typical direct flight time from Philadelphia to Chicago is approximately 2 hours and 25 minutes, covering a distance of 1073 kilometers. For flights with one stop, the median travel time historically extends significantly to about 14 hours and 41 minutes. This difference highlights the considerable time savings associated with choosing a direct route for this journey.

How often do Philadelphia to Chicago flight prices drop?

Historically, flight prices for the Philadelphia to Chicago route tend to drop frequently. This route is classified as one where price fluctuations occur often, providing travelers with regular opportunities to find more favorable fares. Travelers monitoring this route may observe price changes across the trailing 30 days.

Flights From Philadelphia

To Chicago

Cheap Flights from Philadelphia to Chicago

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Deals from

Philadelphia

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated today

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Fares are subject to change and may not be available for all dates. (Data last updated Nov 2, 2026.)

Today’s best flight deals from Philadelphia to Chicago

Explore current cheapest deals departing from Philadelphia to Chicago

2027-02-08 – 2027-02-26
PHL - Chicago
78% AI deal score
$107
$53
Round trip
2027-02-05 – 2027-02-08
PHL - Chicago
48% AI deal score
$118
$53
Round trip
2027-02-22 – 2027-02-26
PHL - Chicago
46% AI deal score
$118
$53
Round trip
2027-02-05 – 2027-02-26
PHL - Chicago
76% AI deal score
$105
$58
Round trip
2027-02-23 – 2027-02-26
PHL - Chicago
76% AI deal score
$215
$94
Round trip
2027-02-05 – 2027-02-23
PHL - Chicago
74% AI deal score
$190
$94
Round trip
2027-02-24 – 2027-02-26
PHL - Chicago
76% AI deal score
$214
$94
Round trip
2027-01-22 – 2027-02-05
PHL - Chicago
43% AI deal score
$98
$96
Round trip
2026-12-19 – 2026-12-21
PHL - Chicago
65% AI deal score
$138
$97
Round trip
2027-02-19 – 2027-02-26
PHL - Chicago
48% AI deal score
$117
$97
Round trip

Philadelphia to Chicago: Overview

Insights for flights from Philadelphia to Chicago

For cheap flights from Philadelphia to Chicago, fares typically range from $274 to $603, with a median price of $374. Right now, current fares are above the typical level, and only 2% of recent fares were classified as a good price. New deals appear almost daily, so setting a price alert can help you track optimal times to book.

When is the cheapest time to fly from Philadelphia to Chicago? The most affordable month to fly is January, with a median fare of $129. Other budget-friendly options include September, with a median of $351, and October, where the median fare is $364.

Regarding direct flights from Philadelphia to Chicago, 22.7% of recent itineraries are non-stop. This means most itineraries connect at least once, with the typical connecting flight involving 2 stopovers.

How long is the flight from Philadelphia to Chicago? A typical journey from Philadelphia to Chicago takes about 2h 25m, including connections. For non-stop flights, the median duration is also 2h 25m, while connecting flights have a significantly longer median duration of 29h 1m.

The distance between Philadelphia and Chicago is approximately 1073 kilometers, classifying this as a short-haul route.

How much is a round trip from Philadelphia to Chicago

Regular price: $90 - $206

Prices are currently below the regular range for flights from Philadelphia to Chicago.

The regular price range for flights from Philadelphia to Chicago is typically between $90 and $206. The current lowest deal is $53 with Frontier Airlines for travel from Feb 5-Feb 8.

now $53

Low $90

High $206

The cheapest time to fly from Philadelphia to Chicago

The cheapest month to fly from Philadelphia to Chicago is January, with a median price of $129. The most expensive month is July, with a median price of $560. Prices are generally lower from January to October.

January

Cheapest

Flights from $129

July

Most Expensive

Flights from $560

Jan

Feb

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Philadelphia to Chicago

Frontier Airlines

Last-minute flights going from Philadelphia to Chicago

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$112

$117

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$88

$117

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$91

$117

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$101

$135

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$90

$135

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$88

$135

One-way

Biggest price drops on these dates for flights from Philadelphia to Chicago

2 nights

Dec 10 - Dec 12

$257 → $113

56%

7 nights

Dec 22 - Dec 29

$320 → $176

45%

2 nights

Oct 27 - Oct 29

$438 → $304

31%

2 nights

Oct 29 - Oct 31

$380 → $247

35%

Popular Airports to fly from Philadelphia to Chicago

Philadelphia - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from PHL to CHI are above the typical level, with a median price of $374.

📅 Best time to fly

January is historically cheapest

Historically, January is the cheapest month to fly from PHL to CHI, with a median price of $129.

⏱️ Flight duration

Direct flights take 2h 25m

Direct flights from Philadelphia to Chicago typically take 2 hours and 25 minutes.

✈️ Airlines & availability

Connecting flights are dominant

About 22.7% of recent flights from PHL to CHI are direct, making connecting flights dominant.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines has direct flights available from Philadelphia International to O Hare International.

🎯 Booking tip

Deals are frequent

Deals on flights from Philadelphia to Chicago are frequent, appearing often in the last 30 days.

Philadelphia main airports to depart from

Philadelphia International (PHL)

Cheapest

Philadelphia International Airport is a convenient option for flights from Philadelphia to Chicago.

📍 ~11 km from Philadelphia city center (reachable by car or train).

💸 Flights from ~$98

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering many flight options for your trip to Chicago.

📍 ~25 km from Chicago city center (reachable by car, train, bus).

💸 Flights from ~$133

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$230

Business & First Class Flight Deals to Chicago

66% AI deal score

$3,180

$2,395

Save $785

Air Canada, +1

Business Class

From PHL

Elite

Dec 01

Chicago, United States

66% AI deal score

$3,063

$2,396

Save $667

Air Canada, +1

Business Class

From PHL

Elite

Dec 01

Chicago, United States

66% AI deal score

$3,078

$2,414

Save $664

Air Canada, +1

Business Class

From PHL

Elite

Dec 01

Chicago, United States

66% AI deal score

$3,083

$2,414

Save $669

Air Canada, +1

Business Class

From PHL

Elite

Nov 26

Chicago, United States

50% AI deal score

$2,744

$2,395

Save $349

Air Canada, +1

Business Class

From PHL

Elite

Dec 11

Chicago, United States

49% AI deal score

$2,402

$2,237

Save $165

Alaska Airlines, Inc.

Business Class

From PHL

Elite

Nov 26

Chicago, United States

49% AI deal score

$2,761

$2,413

Save $348

Air Canada, +1

Business Class

From PHL

Elite

Nov 26

Chicago, United States

49% AI deal score

$2,767

$2,413

Save $354

Air Canada, +1

Business Class

From PHL

Elite

Nov 26

Chicago, United States

49% AI deal score

$2,779

$2,413

Save $366

Air Canada, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the best time to book flights from Philadelphia to Chicago is typically 0-6 days before departure. During this period, the average price observed across the trailing quarter was $406. Prices tend to increase for bookings made further in advance, with flights booked 7-13 days out averaging $680. Even bookings made 60+ days in advance had a higher average price of $509, indicating that last-minute bookings often offer more favorable pricing for this route.

Across the trailing 90 days, a flight from Philadelphia to Chicago is considered a good deal if it is priced at or below $274. This threshold represents the 25th percentile of prices observed for this route. The median price for flights on this route was $374, while prices at the 75th percentile reached $603. Therefore, aiming for prices under $274 indicates a strong value.

Historically, January has offered the cheapest flights from Philadelphia to Chicago, with a median price of $129. Other months that typically present more affordable options include September, with a median price of $351, and October, with a median price of $364. The annual median price for this route was $374, indicating that January provides a significant saving compared to the yearly average.

Related routes

More routes from Philadelphia

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Flights to Chicago from other cities

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Philadelphia to Chicago: Overview

Insights for flights from Philadelphia to Chicago

The distance between Philadelphia and Chicago is approximately 1073 kilometers, classifying this as a short-haul route.

How much is a round trip from Philadelphia to Chicago

Regular price: $90 - $206

Prices are currently below the regular range for flights from Philadelphia to Chicago.

The regular price range for flights from Philadelphia to Chicago is typically between $90 and $206. The current lowest deal is $53 with Frontier Airlines for travel from Feb 5-Feb 8.

now $53

Low $90

High $206

The cheapest time to fly from Philadelphia to Chicago

January

Cheapest

Flights from $129

July

Most Expensive

Flights from $560

Jan

Feb

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Philadelphia to Chicago

Frontier Airlines

Last-minute flights going from Philadelphia to Chicago

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$112

$117

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$88

$117

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$91

$117

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$101

$135

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$90

$135

One-way

Wed, Nov 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (ORD)

Frontier Airlines

$88

$135

One-way

Biggest price drops on these dates for flights from Philadelphia to Chicago

2 nights

Dec 10 - Dec 12

$257 → $113

56%

7 nights

Dec 22 - Dec 29

$320 → $176

45%

2 nights

Oct 27 - Oct 29

$438 → $304

31%

2 nights

Oct 29 - Oct 31

$380 → $247

35%

Popular Airports to fly from Philadelphia to Chicago

Philadelphia - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from PHL to CHI are above the typical level, with a median price of $374.

📅 Best time to fly

January is historically cheapest

Historically, January is the cheapest month to fly from PHL to CHI, with a median price of $129.

⏱️ Flight duration

Direct flights take 2h 25m

Direct flights from Philadelphia to Chicago typically take 2 hours and 25 minutes.

✈️ Airlines & availability

Connecting flights are dominant

About 22.7% of recent flights from PHL to CHI are direct, making connecting flights dominant.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines has direct flights available from Philadelphia International to O Hare International.

🎯 Booking tip

Deals are frequent

Deals on flights from Philadelphia to Chicago are frequent, appearing often in the last 30 days.

Philadelphia main airports to depart from

Philadelphia International (PHL)

Cheapest

Philadelphia International Airport is a convenient option for flights from Philadelphia to Chicago.

📍 ~11 km from Philadelphia city center (reachable by car or train).

💸 Flights from ~$98

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering many flight options for your trip to Chicago.

📍 ~25 km from Chicago city center (reachable by car, train, bus).

💸 Flights from ~$133

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$230

Chicago, United States

49% AI deal score

$2,779

$2,413

Save $366

Air Canada, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Philadelphia to Chicago

Today’s best flight deals from Philadelphia to Chicago

Philadelphia to Chicago: Overview

Insights for flights from Philadelphia to Chicago

How much is a round trip from Philadelphia to Chicago

The cheapest time to fly from Philadelphia to Chicago

Direct flights from Philadelphia to Chicago

Last-minute flights going from Philadelphia to Chicago

Biggest price drops on these dates for flights from Philadelphia to Chicago

Popular Airports to fly from Philadelphia to Chicago

Philadelphia - Chicago route insights

Recent fares are above the typical level

January is historically cheapest

Direct flights take 2h 25m

Connecting flights are dominant

Frontier Airlines offers direct flights

Deals are frequent

Philadelphia main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Nov 09

Nov 20

Nov 09

Dec 08

Dec 01

Dec 01

Dec 01

Nov 26

Dec 11

Nov 26

Nov 26

Nov 26

Frequently Asked Questions About Flights to Chicago

When is the best time to book flights from Philadelphia to Chicago?

How do I know if a Philadelphia to Chicago flight is a good deal?

Which months have the cheapest flights from Philadelphia to Chicago?

Are there direct flights from Philadelphia to Chicago?

What's the flight time from Philadelphia to Chicago?

How often do Philadelphia to Chicago flight prices drop?

Related routes

More routes from Philadelphia

Flights to Chicago from other cities

Philadelphia to Chicago: Overview

Insights for flights from Philadelphia to Chicago

How much is a round trip from Philadelphia to Chicago

The cheapest time to fly from Philadelphia to Chicago

Direct flights from Philadelphia to Chicago

Last-minute flights going from Philadelphia to Chicago

Biggest price drops on these dates for flights from Philadelphia to Chicago

Popular Airports to fly from Philadelphia to Chicago

Philadelphia - Chicago route insights

Recent fares are above the typical level

January is historically cheapest

Direct flights take 2h 25m

Connecting flights are dominant

Frontier Airlines offers direct flights

Deals are frequent

Philadelphia main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Nov 09

Nov 20

Nov 09

Dec 08

Dec 01

Dec 01

Dec 01

Nov 26

Dec 11

Nov 26

Nov 26

Nov 26

Frequently Asked Questions About Flights to Chicago

When is the best time to book flights from Philadelphia to Chicago?

How do I know if a Philadelphia to Chicago flight is a good deal?

Which months have the cheapest flights from Philadelphia to Chicago?