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Flight Deals from Philadelphia to Chicago from $60

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Stops

  • Nonstop
    from $111
  • Up to 1 stop
    $196

Airlines

  • American Airlines
    $238
  • CitizenPlane
    $122
  • Delta Air Lines
    $196
  • Frontier Airlines
    $111
  • JetBlue
    $225
  • United Airlines
    $258
  • Virgin Atlantic
    $236

Cabin Class

  • Economy
    $111

Departure Airports

  • Philadelphia International Airport
    $111
  • Trenton Mercer Airport
    $291

Arrival Airports

  • Chicago Midway Airport
    $121
  • Chicago O Hare Airport
    $111

Layover Airports

  • Cleveland Hopkins International Airport
    $283
  • Dallas Fort Worth International Airport
    $207
  • Denver International Airport
    $207
  • Detroit Metropolitan Airport
    $196
  • General Edward Lawrence Logan International Airport
    $225
  • Hartsfield Jackson Atlanta International Airport
    $196
  • John Glenn Columbus International Airport
    $288
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $236
  • Nashville International Airport
    $288
  • Orlando International Airport
    $291
  • Raleigh Durham International Airport
    $238
  • Reagan Washington National Airport
    $266
  • Washington Dulles Airport
    $268

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On average save $240 per traveler
Frontier Airlines Logo
Frontier Airlines

06/22/25

PHL
1h 32m
Direct

06/22/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/27/25

ORD
3h 27m
Direct

06/27/25

PHL
$111
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/04/25

PHL
1h 13m
Direct

07/04/25

MDW
Frontier Airlines Logo
Frontier Airlines

07/11/25

MDW
3h 5m
Direct

07/11/25

PHL
$121
Free cancellation within 83 hours of booking
CitizenPlane Logo
CitizenPlane

06/22/25

PHL
1h 32m
Direct

06/22/25

ORD
CitizenPlane Logo
CitizenPlane

06/27/25

ORD
3h 27m
Direct

06/27/25

PHL
$122
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/03/25

PHL
4h 3m
DTW

07/03/25

ORD
Delta Air Lines Logo
Delta Air Lines

07/05/25

ORD
7h 46m
ATL

07/05/25

PHL
$196
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/13/25

PHL
1h 13m
Direct

06/13/25

MDW
Frontier Airlines Logo
Frontier Airlines

06/20/25

MDW
9h 35m
DEN

06/20/25

PHL
$207
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/04/25

PHL
1h 13m
Direct

07/04/25

MDW
Frontier Airlines Logo
Frontier Airlines

07/11/25

MDW
10h 48m
DFW

07/11/25

PHL
$207
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/22/25

PHL
1h 32m
Direct

06/22/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/27/25

ORD
6h 22m
ATL

06/27/25

PHL
$214
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/29/25

PHL
4h 3m
DTW

06/29/25

ORD
Delta Air Lines Logo
Delta Air Lines

07/05/25

ORD
7h 11m
ATL

07/05/25

PHL
$216
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

06/24/25

PHL
5h 38m
BOS

06/24/25

ORD
JetBlue Logo
JetBlue

07/01/25

ORD
9h 3m
BOS

07/01/25

PHL
$225
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/12/25

PHL
1h 32m
Direct

06/12/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/16/25

ORD
23h 30m
DEN

06/17/25

PHL
$228
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/12/25

PHL
2h 41m
DTW

06/12/25

MDW
Delta Air Lines Logo
Delta Air Lines

06/16/25

MDW
7h 8m
MSP

06/16/25

PHL
$236
Free cancellation within 83 hours of booking
Virgin Atlantic Logo
Virgin Atlantic

06/12/25

PHL
7h 12m
ATL

06/12/25

ORD
Virgin Atlantic Logo
Virgin Atlantic

06/15/25

ORD
7h 31m
ATL

06/15/25

PHL
$236
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/22/25

PHL
1h 32m
Direct

06/22/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/27/25

ORD
9h 52m
RDU

06/27/25

PHL
$238
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/24/25

PHL
1h 36m
Direct

06/24/25

ORD
American Airlines Logo
American Airlines

07/01/25

ORD
3h 9m
Direct

07/02/25

PHL
$238
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/20/25

PHL
1h 13m
Direct

06/20/25

MDW
Frontier Airlines Logo
Frontier Airlines

06/27/25

MDW
10h 48m
DFW

06/27/25

PHL
$238
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/10/25

PHL
1h 25m
Direct

06/10/25

ORD
American Airlines Logo
American Airlines

06/17/25

ORD
3h 9m
Direct

06/18/25

PHL
$246
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/04/25

PHL
1h 24m
Direct

07/04/25

ORD
United Airlines Logo
United Airlines

07/07/25

ORD
3h 7m
Direct

07/08/25

PHL
$258
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/30/25

PHL
1h 25m
Direct

06/30/25

ORD
United Airlines Logo
United Airlines

07/04/25

ORD
3h 16m
Direct

07/04/25

PHL
$258
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/22/25

PHL
3h 7m
DCA

06/22/25

ORD
American Airlines Logo
American Airlines

06/27/25

ORD
2h 56m
Direct

06/27/25

PHL
$266
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/13/25

PHL
1h 25m
Direct

06/13/25

ORD
United Airlines Logo
United Airlines

07/01/25

ORD
5h 16m
IAD

07/01/25

PHL
$268
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/04/25

PHL
6h 12m
IAD

07/04/25

ORD
United Airlines Logo
United Airlines

07/07/25

ORD
3h 7m
Direct

07/08/25

PHL
$268
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/02/25

PHL
3h 13m
CLE

07/02/25

ORD
American Airlines Logo
American Airlines

07/09/25

ORD
3h 3m
Direct

07/09/25

PHL
$283
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/13/25

PHL
4h 44m
DCA

06/13/25

ORD
American Airlines Logo
American Airlines

07/01/25

ORD
3h 9m
Direct

07/02/25

PHL
$288
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/29/25

PHL
3h 45m
BNA

06/29/25

ORD
American Airlines Logo
American Airlines

07/03/25

ORD
3h 2m
Direct

07/03/25

PHL
$288
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/28/25

PHL
4h 34m
RDU

06/28/25

ORD
American Airlines Logo
American Airlines

07/05/25

ORD
3h 8m
Direct

07/05/25

PHL
$288
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/26/25

PHL
3h 34m
CMH

06/26/25

ORD
American Airlines Logo
American Airlines

07/03/25

ORD
3h 2m
Direct

07/03/25

PHL
$288
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/11/25

PHL
7h 6m
MSP

06/11/25

MDW
Delta Air Lines Logo
Delta Air Lines

06/18/25

MDW
8h 49m
MSP

06/18/25

PHL
$290
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/03/25

TTN
15h 36m
MCO

07/04/25

ORD
Frontier Airlines Logo
Frontier Airlines

07/07/25

ORD
6h 21m
ATL

07/07/25

TTN
$291
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/03/25

PHL
10h 24m
MCO

07/04/25

ORD
Frontier Airlines Logo
Frontier Airlines

07/07/25

ORD
3h 26m
Direct

07/07/25

PHL
$293
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/10/25

PHL
2h 39m
CMH

06/10/25

ORD
American Airlines Logo
American Airlines

06/17/25

ORD
3h 2m
Direct

06/17/25

PHL
$296
Free cancellation within 83 hours of booking

Top Deals on flights from Philadelphia to Chicago

Philadelphia, US (PHL) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jul 14

PHL
1h 13m
Direct

Jul 14

MDW

as low as

$60

Philadelphia, US (PHL) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jul 27

PHL
1h 30m
Direct

Jul 27

ORD

as low as

$60

Philadelphia, US (PHL) - Chicago, US (CHI)

CitizenPlane Logo
CitizenPlane

Jun 22

PHL
1h 32m
Direct

Jun 22

ORD

as low as

$62

Philadelphia, US (PHL) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 1

PHL
4h 11m
ATL

Jul 1

MDW

as low as

$98

Philadelphia, US (PHL) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 25

PHL
3h 18m
DTW

May 25

ORD

as low as

$98

Philadelphia, US (PHL) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

Jun 4

PHL
16h 4m
FLL

Jun 4

ORD

as low as

$102

Philadelphia, US (PHL) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jun 3

TTN
6h 19m
MCO

Jun 4

ORD

as low as

$103

Philadelphia, US (PHL) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 6

PHL
1h 36m
Direct

Jun 6

ORD

as low as

$108

Philadelphia, US (PHL) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 21

PHL
4h 2m
BOS

May 21

ORD

as low as

$110

Philadelphia, US (PHL) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

Oct 7

PHL
16h 2m
MIA

Oct 7

ORD

as low as

$112

Philadelphia, US (PHL) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Aug 30

PHL
1h 22m
Direct

Aug 30

ORD

as low as

$115

Philadelphia, US (PHL) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 30

PHL
4h 20m
MSP

May 30

ORD

as low as

$118

Frequently Asked Questions

What is the typical flight duration from Philadelphia to Chicago?
The typical flight from Philadelphia to Chicago usually takes between 1.5 to 2.5 hours, depending on factors such as air traffic and weather conditions. Flights are generally direct, offering a swift travel experience. For travelers concerned about time management, checking real-time flight schedules is advisable as slight variations can occur. This timeframe allows for quick city-to-city transit, making it a popular route for business and leisure. Ensure you verify your specific flight details ahead of departure for the most accurate information.
Are there any direct flights from Philadelphia to Chicago?
Yes, there are direct flights available from Philadelphia to Chicago. This service is offered by several major carriers, ensuring a convenient and efficient travel experience without the need for layovers. Direct flights typically reduce travel hassle and help maintain tighter schedules. When booking, consider comparing departure times and prices since direct services can vary throughout the day. This is particularly beneficial for travelers looking to maximize their time at either location, and it adds simplicity to the overall journey.
What are the best transportation options from Chicago airport to downtown?
When arriving in Chicago, travelers have various transportation options to reach downtown. The most popular choices include the efficient CTA train services, which typically cost between $5 to $10 and take about 30 to 45 minutes. Ride-sharing services and taxis offer door-to-door convenience and usually range from $30 to $60, depending on traffic conditions. Additionally, airport shuttles and rental cars are available for further flexibility. Considering your priorities of cost versus convenience will help determine the best method for your trip.
What are the must-see attractions in Chicago for travelers arriving from Philadelphia?
For those visiting Chicago from Philadelphia, several iconic attractions should be on your list. Highlights include Millennium Park with its famous Cloud Gate sculpture, the Art Institute of Chicago for art enthusiasts, and Navy Pier offering waterfront views and entertainment. Don't miss exploring the historic architecture along the Chicago Riverwalk and perhaps a visit to the Willis Tower Skydeck for breathtaking city vistas. Each location offers a unique perspective of the city’s vibrant culture, blending modern attractions with historical significance for a memorable travel experience.
Which local dishes should travelers from Philadelphia try when visiting Chicago?
Travelers making their way from Philadelphia to Chicago should sample the city’s unique culinary offerings. A must-try dish is Chicago-style deep-dish pizza, known for its thick crust and generous toppings, and the classic Chicago-style hot dog with its distinctive array of toppings. Additionally, savor an Italian Beef sandwich for a taste of local tradition. Each dish is widely available in many eateries across the city, offering a blend of hearty flavors and a distinctive regional twist that sets Chicago’s dining scene apart from other major cities.
What are the best family-friendly activities in Chicago for visitors from Philadelphia?
Chicago offers a variety of family-friendly activities perfect for visitors arriving from Philadelphia. Enjoy a day at the Shedd Aquarium or the Field Museum, both providing engaging exhibits for all ages. Navy Pier features rides, interactive installations, and seasonal events suitable for children. Meanwhile, Lincoln Park Zoo offers complimentary admission and interactive animal exhibits. Each option provides educational enrichment and fun, making it easy to craft an itinerary that pleases both kids and adults. Consider pre-booking tickets during peak seasons for a smoother experience.
Are there any budget-friendly hotels in Chicago for travelers from Philadelphia?
Yes, Chicago offers several budget-friendly hotel options that accommodate travelers coming from Philadelphia. Many affordable accommodations are available near downtown and public transit hubs, with rates typically ranging from $100 to $200 per night. These hotels often emphasize convenience, comfort, and proximity to key attractions such as shopping districts and cultural landmarks. It is advisable to compare rates online and read recent reviews to ensure you secure a deal that meets your needs. Booking in advance during off-peak travel seasons can also provide better rates and availability.
What are the unique cultural experiences in Chicago that travelers from Philadelphia should not miss?
Travelers from Philadelphia should immerse themselves in Chicago’s rich cultural landscape by exploring diverse neighborhoods and art scenes. Visit areas like Pilsen for vibrant murals and local galleries, or Bronzeville to experience historic jazz clubs and community-driven art. Attending local festivals, visiting community theaters, or joining food tours highlights the blend of diverse cultures present in the city. Moreover, engaging in public art installations and cultural museums can deepen your understanding of Chicago’s creative spirit. These experiences provide a deep dive into the city’s unique heritage and community narratives.
What are the top shopping districts in Chicago for visitors from Philadelphia?
Chicago’s shopping scene offers a mix of high-end, boutique, and mainstream options that appeal to visitors from Philadelphia. The Magnificent Mile is renowned for its luxury brands and flagship stores, while State Street provides a more eclectic mix of mainstream retailers and local shops. For a unique experience, explore areas like Wicker Park and the West Loop, where independent boutiques and artisanal stores abound. Each district has its own character, so consider your shopping preferences and proximity to dining or cultural attractions to maximize your day exploring the city’s retail diversity.
Is there a specific time of year when Chicago is best visited by travelers from Philadelphia?
Yes, the best time to visit Chicago is generally during late spring to early fall, particularly from May to September. During this period, the weather is mild, making it ideal for outdoor attractions, festivals, and exploring urban parks. Summer also sees numerous events like outdoor concerts and cultural festivals, although it may be busier. Fall offers vibrant foliage and fewer crowds. Travelers from Philadelphia can enjoy a balance of pleasant weather and active city life, but always check local event calendars as seasonal variations may enhance your experience even further.
What health precautions should travelers from Philadelphia consider before visiting Chicago?
Travelers from Philadelphia should prepare for Chicago’s variable climate by packing accordingly and staying updated on seasonal health advisories. It’s wise to carry a travel health kit, including basic medications, hand sanitizers, and sunscreen for summer outings. During colder months, dress in layers and consider flu vaccinations if you’re visiting during peak season. Additionally, checking local air quality and allergy forecasts can help if you have respiratory concerns. Staying informed through local health department updates and covering your essential vaccines ensures a safe and well-prepared visit.
What are the customs requirements for travelers flying from Philadelphia to Chicago?
Since the flight between Philadelphia and Chicago is a domestic route within the United States, there aren’t any customs requirements typically associated with international travel. However, travelers must adhere to TSA security guidelines at the airport. It is recommended to carry a valid government-issued ID, and be aware of restrictions on liquids and prohibited items in your carry-on. This streamlined process allows for a hassle-free domestic flight, though always check for any updated travel advisories or changes in security protocols before your departure.
Are there any seasonal events in Chicago that travelers from Philadelphia should not miss?
Absolutely, Chicago hosts a variety of seasonal events that are well worth experiencing. In the summer, events like the Taste of Chicago and the Chicago Air and Water Show draw large crowds with an array of food, music, and entertainment. In the winter, festive holiday markets and ice skating rinks create a cozy atmosphere. Spring and fall festivals also celebrate the city’s art, culture, and culinary scenes. These varied events offer travelers from Philadelphia an opportunity to enjoy the city’s vibrant community spirit throughout the year.
What are the best solo travel activities in Chicago for travelers arriving from Philadelphia?
Solo travelers can explore Chicago on foot or via public transportation to experience an array of activities. Visiting local museums such as the Art Institute or the Museum of Contemporary Art offers thoughtful engagement with the city’s cultural heritage. Wander through neighborhoods like Hyde Park or Wicker Park to discover hidden cafes, independent bookstores, and vibrant street art. City tours, whether walking or bike-based, provide insightful commentary on historical landmarks and contemporary life. These activities offer flexibility and personal enrichment for those traveling alone.
What airport amenities in Chicago are available for travelers arriving from Philadelphia?
Chicago’s major airports are well-equipped with a range of amenities to enhance traveler comfort. Facilities typically include free Wi-Fi, numerous dining options with diverse cuisines, and comfortable lounges available for purchase or with certain credit cards. Retail shops, currency exchange services, and even shower facilities are common in busy hubs like O'Hare and Midway. For those with time to spare, dedicated relaxation zones and charging stations are available as well. Planning your arrival by reviewing airport maps and available services can help make your transition from flight to city life smoother.
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