Are there direct flights from Philadelphia to Chicago?

Yes, direct flights are available from Philadelphia to Chicago. Historically, direct flights have accounted for 48.3% of the routes. For flights that include stopovers, the median number of stopovers observed was 2. Travelers have a good chance of finding a non-stop option for this route.

What's the flight time from Philadelphia to Chicago?

The typical direct flight time from Philadelphia to Chicago is 2 hours and 29 minutes, covering a distance of 1073 kilometers. Flights with one stopover generally take longer, with a median duration of 7 hours and 21 minutes. Travelers can expect a relatively short journey when flying non-stop between these two cities.

How often do Philadelphia to Chicago flight prices drop?

Historically, flight prices for the Philadelphia to Chicago route have shown frequent drops. This indicates that travelers may often find opportunities to secure more affordable fares. The pricing for this route tends to be dynamic, with frequent fluctuations observed 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 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Philadelphia to Chicago

Explore current cheapest deals departing from Philadelphia to Chicago

2026-09-07 – 2026-09-10
PHL - Chicago
42% AI deal score
$119
$121
Round trip
2026-08-17 – 2026-08-20
PHL - Chicago
45% AI deal score
$137
$122
Round trip
2026-09-17 – 2026-09-21
PHL - Chicago
42% AI deal score
$119
$122
Round trip
2026-10-01 – 2026-10-05
PHL - Chicago
42% AI deal score
$122
$122
Round trip
2026-10-22 – 2026-10-29
PHL - Chicago
42% AI deal score
$124
$125
Round trip
2026-09-07 – 2026-09-11
PHL - Chicago
42% AI deal score
$119
$126
Round trip
2026-08-15 – 2026-08-20
PHL - Chicago
43% AI deal score
$131
$127
Round trip
2026-09-06 – 2026-09-11
PHL - Chicago
41% AI deal score
$117
$127
Round trip
2026-09-10 – 2026-09-17
PHL - Chicago
41% AI deal score
$113
$127
Round trip
2026-11-09 – 2026-11-12
PHL - Chicago
44% AI deal score
$136
$127
Round trip

Philadelphia to Chicago: Overview

Insights for flights from Philadelphia to Chicago

For cheap flights from Philadelphia to Chicago, fares typically range from $168–$461, with a median of $248. Right now, current fares are significantly above the typical level, indicating a less opportune time for booking. Only 7% of recent fares were classified as a good price, suggesting that finding a bargain on this route can be challenging.

When is the cheapest time to fly from Philadelphia to Chicago? The most affordable months to fly are October and September, both with a median fare of $164. April also offers competitive pricing, with a median fare of $169. These months present the best opportunities for travelers to secure lower prices.

Regarding direct flights from Philadelphia to Chicago, 48.3% of recent itineraries are non-stop, meaning a meaningful share are non-stop, the rest connect once. For itineraries that include connections, the typical number of stopovers is 2.

How long is the flight from Philadelphia to Chicago? A typical journey from Philadelphia to Chicago takes about 2h 29m, including connections. This median duration reflects both non-stop and connecting flights on this route.

The distance between Philadelphia and Chicago is 1073 kilometers, classifying this as a short-haul route. This means you can expect a relatively quick journey, making it a convenient option for travelers.

How much is a round trip from Philadelphia to Chicago

Regular price: $91 - $226

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

The regular price range for this route is $91 to $226. The current lowest deal is $121 with Frontier Airlines for travel from Sep 7-Sep 10.

now $121

Low $91

High $226

The cheapest time to fly from Philadelphia to Chicago

The cheapest month to fly from Philadelphia to Chicago is October, with a median price of $164. The most expensive month is August, with a median price of $357. Prices are generally lower from January to November.

October

Cheapest

Flights from $164

August

Most Expensive

Flights from $357

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Philadelphia to Chicago

Frontier Airlines

Last-minute flights going from Philadelphia to Chicago

Sat, Aug 1

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$368

$236

One-way

Sat, Aug 1

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$440

$249

One-way

Sat, Aug 1

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$444

$293

One-way

Tue, Aug 4

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$347

$217

One-way

Tue, Aug 4

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$393

$289

One-way

Sun, Aug 9

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$269

$194

One-way

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

2 nights

Aug 1 - Aug 3

$440 → $249

43%

1 night

Aug 1 - Aug 2

$444 → $293

34%

6 nights

Aug 1 - Aug 7

$368 → $236

36%

9 nights

Aug 4 - Aug 13

$347 → $217

37%

Popular Airports to fly from Philadelphia to Chicago

Philadelphia - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Philadelphia to Chicago are above the typical level at $121.

📅 Best time to fly

Fly in October for the best prices

Historically, October offers the lowest median prices at $164 for this route.

⏱️ Flight duration

Direct flights average 2h 29m

The typical direct flight from Philadelphia to Chicago takes 2 hours and 29 minutes.

✈️ Airlines & availability

Frontier Airlines offers direct flights

Frontier Airlines provides direct flight options for the Philadelphia to Chicago route.

🏆 Airline highlight

Frontier Airlines has direct deals

Frontier Airlines has 1 direct deal available for flights from Philadelphia to Chicago.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Philadelphia to Chicago appear frequently, with 7% good prices.

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 city center (reachable by car or train)

💸 Flights from ~$51

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

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

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

💸 Flights from ~$51

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers a major international hub with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by rail or car), requires travel across state lines.

💸 Flights from ~$238

Business & First Class Flight Deals to Chicago

78% AI deal score

$5,275

$1,945

Save $3,330

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Philadelphia to Chicago is typically 14-27 days before departure. During this period, the average price observed was $237. Booking within 0-6 days of departure generally sees a significant price increase, with an average of $654. Planning ahead by at least two weeks can lead to more favorable prices.

Across the trailing quarter, a good deal for a flight from Philadelphia to Chicago is considered to be $168 or less. The median price for this route has been $248. Prices can vary, with the 75th percentile reaching $461, indicating that a price below the median is generally a favorable option.

Historically, October and September have offered the cheapest flights from Philadelphia to Chicago, both with a median price of $164. April also presented competitive pricing, with a median of $169. The annual median price for this route is $248, suggesting that these months are notably more affordable for travelers.

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

How much is a round trip from Philadelphia to Chicago

Regular price: $91 - $226

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

The regular price range for this route is $91 to $226. The current lowest deal is $121 with Frontier Airlines for travel from Sep 7-Sep 10.

now $121

Low $91

High $226

The cheapest time to fly from Philadelphia to Chicago

October

Cheapest

Flights from $164

August

Most Expensive

Flights from $357

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Philadelphia to Chicago

Frontier Airlines

Last-minute flights going from Philadelphia to Chicago

Sat, Aug 1

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$368

$236

One-way

Sat, Aug 1

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$440

$249

One-way

Sat, Aug 1

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$444

$293

One-way

Tue, Aug 4

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$347

$217

One-way

Tue, Aug 4

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$393

$289

One-way

Sun, Aug 9

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$269

$194

One-way

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

2 nights

Aug 1 - Aug 3

$440 → $249

43%

1 night

Aug 1 - Aug 2

$444 → $293

34%

6 nights

Aug 1 - Aug 7

$368 → $236

36%

9 nights

Aug 4 - Aug 13

$347 → $217

37%

Popular Airports to fly from Philadelphia to Chicago