Are there direct flights from Philadelphia to Chicago?

Yes, direct flights are available from Philadelphia to Chicago. Historically, approximately 48.3% of flights on this route have been direct. For journeys involving connections, the median number of stopovers observed was 2. Travelers can often find options that do not require any intermediate stops.

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. For flights with one stop, the median travel time increases significantly to 7 hours and 21 minutes. This difference highlights the convenience of choosing a direct option when available.

How often do Philadelphia to Chicago flight prices drop?

Historically, flight prices for the Philadelphia to Chicago route have shown frequent price drops. This indicates that travelers may often find opportunities to secure more favorable fares. Monitoring prices regularly can be beneficial for those planning to travel between these two cities.

Flights From Philadelphia

To Chicago

Cheap Flights from Philadelphia to Chicago

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Deals from

Philadelphia

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Prices updated 1 day ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Philadelphia to Chicago

Explore current cheapest deals departing from Philadelphia to Chicago

2026-10-17 – 2026-11-05
PHL - Chicago
70% AI deal score
$93
$70
Round trip
2026-10-17 – 2026-10-29
PHL - Chicago
71% AI deal score
$98
$70
Round trip
2026-10-29 – 2026-10-30
PHL - Chicago
73% AI deal score
$118
$75
Round trip
2026-10-17 – 2026-10-30
PHL - Chicago
69% AI deal score
$97
$75
Round trip
2026-10-17 – 2026-11-13
PHL - Chicago
49% AI deal score
$93
$75
Round trip
2026-10-30 – 2026-11-05
PHL - Chicago
72% AI deal score
$112
$75
Round trip
2026-10-17 – 2026-10-19
PHL - Chicago
72% AI deal score
$118
$77
Round trip
2026-10-30 – 2026-11-13
PHL - Chicago
49% AI deal score
$98
$80
Round trip
2026-10-12 – 2026-10-16
PHL - Chicago
49% AI deal score
$119
$92
Round trip
2026-10-12 – 2026-10-17
PHL - Chicago
48% AI deal score
$116
$94
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 above the typical level. Only 7% of recent fares were classified as a good price, indicating that finding a significant discount may require some flexibility.

When is the cheapest time to fly from Philadelphia to Chicago? You'll find the most budget-friendly options in 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 securing lower prices on this route.

A meaningful share of itineraries from Philadelphia to Chicago are non-stop, with 48.3% of recent fares being direct flights. For the remaining itineraries that include connections, the typical number of stopovers is 2.

How long is the flight from Philadelphia to Chicago? A typical journey, including connections, takes about 2h 29m. This median duration accounts for both direct and connecting itineraries on this route.

The distance between Philadelphia and Chicago is approximately 1073 kilometers. This classifies the route as a short-haul flight, meaning you can expect a relatively quick travel experience.

How much is a round trip from Philadelphia to Chicago

Regular price: $79 - $289

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

The regular price range for flights from Philadelphia to Chicago is between $79 and $289. The current lowest deal is $57 with Frontier Airlines, for travel from Oct 10-Oct 24.

now $57

Low $79

High $289

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

Tue, Sep 15

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$432

$269

One-way

Fri, Sep 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$289

$179

One-way

Mon, Sep 28

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$337

$233

One-way

Thu, Oct 1

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$339

$191

One-way

Thu, Oct 1

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$339

$236

One-way

Fri, Oct 2

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$339

$246

One-way

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

6 nights

Oct 11 - Oct 17

$309 → $138

55%

2 nights

Sep 15 - Sep 17

$432 → $269

38%

4 nights

Oct 11 - Oct 15

$326 → $168

48%

5 nights

Oct 11 - Oct 16

$319 → $166

48%

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 $248.

📅 Best time to fly

Fly in October for the best prices

Historically, October and September offer the lowest median prices at $164.

⏱️ Flight duration

Direct flights average 2h 29m

The median flight time for direct routes is 2h 29m, while connecting flights average 14h 41m.

✈️ Airlines & availability

Mixed availability of direct flights

Direct flights make up 48.3% of routes, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines has direct flight options from Philadelphia to Chicago.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Philadelphia to Chicago are frequent, appearing within a 30-day window.

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 ~$128

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

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

💸 Flights from ~$130

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

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

💸 Flights from ~$217

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Philadelphia to Chicago.

Elite

Air Canada, +1

Business Class

From PHL

Elite

Oct 26

Chicago, United States

80% AI deal score

$5,002

$2,328

Save $2,674

Air Canada, +1

Business Class

From PHL

Elite

Sep 15

Chicago, United States

78% AI deal score

$1,390

$675

Save $715

From PHL

Elite

Oct 28

Chicago, United States

78% AI deal score

$1,332

$691

Save $641

From PHL

Elite

Sep 22

Chicago, United States

76% AI deal score

$6,695

$3,461

Save $3,234

Alaska Airlines, Inc.

Business Class

From PHL

Elite

Oct 05

Chicago, United States

76% AI deal score

$1,124

$631

Save $493

From PHL

Elite

Sep 22

Chicago, United States

76% AI deal score

$1,263

$688

Save $575

From PHL

Elite

Dec 10

Chicago, United States

76% AI deal score

$1,365

$764

Save $601

From PHL

Elite

Oct 26

Chicago, United States

75% AI deal score

$1,302

$791

Save $511

From PHL

Elite

Nov 05

Chicago, United States

73% AI deal score

$647

$521

Save $126

United Airlines

Business Class

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 price of $654. Planning ahead by at least two weeks can lead to more favorable pricing.

Across the trailing quarter, a flight from Philadelphia to Chicago is considered a good deal if it is priced at or below $168. The median price for this route over the same period was $248. Prices exceeding $461 are generally in the more expensive range. Comparing offers to the $168 threshold can help identify value.

Historically, October and September have shown 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, indicating that these months offer notable savings 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. This classifies the route as a short-haul flight, meaning you can expect a relatively quick travel experience.

How much is a round trip from Philadelphia to Chicago

Regular price: $79 - $289

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

The regular price range for flights from Philadelphia to Chicago is between $79 and $289. The current lowest deal is $57 with Frontier Airlines, for travel from Oct 10-Oct 24.

now $57

Low $79

High $289

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

Tue, Sep 15

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$432

$269

One-way

Fri, Sep 25

⌛ Last-Minute

PHL - Chicago

Philadelphia (PHL) - Chicago (MDW)

Frontier Airlines

$289

$179

One-way

Mon, Sep 28

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$337

$233

One-way

Thu, Oct 1

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$339

$191

One-way

Thu, Oct 1

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$339

$236

One-way

Fri, Oct 2

⌛ Last-Minute

TTN - Chicago

Trenton (TTN) - Chicago (ORD)

Frontier Airlines

$339

$246

One-way

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

6 nights

Oct 11 - Oct 17

$309 → $138

55%

2 nights

Sep 15 - Sep 17

$432 → $269

38%

4 nights

Oct 11 - Oct 15

$326 → $168

48%

5 nights

Oct 11 - Oct 16

$319 → $166

48%

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 $248.

📅 Best time to fly

Fly in October for the best prices

Historically, October and September offer the lowest median prices at $164.

⏱️ Flight duration

Direct flights average 2h 29m

The median flight time for direct routes is 2h 29m, while connecting flights average 14h 41m.

✈️ Airlines & availability

Mixed availability of direct flights

Direct flights make up 48.3% of routes, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines has direct flight options from Philadelphia to Chicago.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Philadelphia to Chicago are frequent, appearing within a 30-day window.

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 ~$128

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

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

💸 Flights from ~$130

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

Chicago, United States

78% AI deal score

$1,390

$675

Save $715

From PHL

Elite

Oct 28

Chicago, United States

78% AI deal score

$1,332

$691

Save $641

From PHL

Elite

Sep 22

Chicago, United States

76% AI deal score

$6,695

$3,461

Save $3,234

Alaska Airlines, Inc.

Business Class

From PHL

Elite

Oct 05

Chicago, United States

76% AI deal score

$1,124

$631

Save $493

From PHL

Elite

Sep 22

Chicago, United States

76% AI deal score

$1,263

$688

Save $575

From PHL

Elite

Dec 10

Chicago, United States

76% AI deal score

$1,365

$764

Save $601

From PHL

Elite

Oct 26

Chicago, United States

75% AI deal score

$1,302

$791

Save $511

From PHL

Elite

Nov 05

Chicago, United States

73% AI deal score

$647

$521

Save $126

United Airlines

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

Fly in October for the best prices

Direct flights average 2h 29m

Mixed availability of direct flights

Frontier Airlines offers direct flights

Deals are frequent on this route

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

Oct 21

Oct 19

Oct 25

Oct 26

Sep 15

Oct 28

Sep 22

Oct 05

Sep 22

Dec 10

Oct 26

Nov 05

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

Fly in October for the best prices

Direct flights average 2h 29m

Mixed availability of direct flights

Frontier Airlines offers direct flights

Deals are frequent on this route

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

Oct 21

Oct 19

Oct 25

Oct 26

Sep 15

Oct 28

Sep 22

Oct 05

Sep 22

Dec 10

Oct 26

Nov 05

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?