$35 Cheap flight deals from Philadelphia (ILG) to Oak Park (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Philadelphia to Oak Park

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 29 - Tue, Dec 2
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$259 Roundtrip, just found
$259
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Nov 29 from Philadelphia Intl. to O'Hare Intl., returning Tue, Dec 2, priced at $259 just found
Sat, Nov 29 - Sat, Nov 29
PHL
Philadelphia Intl.
MDW
Midway Intl.
$287 Roundtrip, found 6 hours ago
$287
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Nov 29 from Philadelphia Intl. to Midway Intl., returning Sat, Nov 29, priced at $287 found 6 hours ago
Fri, Nov 28 - Sun, Nov 30
TTN
Mercer
ORD
O'Hare Intl.
$576 Roundtrip, found 2 days ago
$576
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 28 from Mercer to O'Hare Intl., returning Sun, Nov 30, priced at $576 found 2 days ago
Fri, Nov 28 - Tue, Dec 2
PHL
Philadelphia Intl.
RFD
Greater Rockford
$634 Roundtrip, found 13 hours ago
$634
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Fri, Nov 28 from Philadelphia Intl. to Greater Rockford, returning Tue, Dec 2, priced at $634 found 13 hours ago

Airfares from $35 One Way, $68 Round Trip from Philadelphia to Oak Park

Prices starting at $68 for return flights and $35 for one-way flights to Oak Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 23 - Mon, Jan 26
PHL
Philadelphia
ORD
Chicago
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jan 23 from Philadelphia to Chicago, returning Mon, Jan 26, priced at $68 just found
Tue, Dec 9 - Wed, Dec 10
PHL
Philadelphia
ORD
Chicago
$86 Roundtrip, found 20 hours ago
$86
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Dec 9 from Philadelphia to Chicago, returning Wed, Dec 10, priced at $86 found 20 hours ago
Mon, Dec 8 - Thu, Dec 18
PHL
Philadelphia
MDW
Chicago
$134 Roundtrip, found 5 days ago
$134
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Dec 8 from Philadelphia to Chicago, returning Thu, Dec 18, priced at $134 found 5 days ago
Wed, Jan 7 - Tue, Jan 13
TTN
Trenton
ORD
Chicago
$139 Roundtrip, found 5 days ago
$139
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Jan 7 from Trenton to Chicago, returning Tue, Jan 13, priced at $139 found 5 days ago
Wed, Jan 7 - Tue, Jan 13
PHL
Philadelphia
ORD
Chicago
$139 Roundtrip, found 5 days ago
$139
Roundtrip
found 5 days ago
Select United flight, departing Wed, Jan 7 from Philadelphia to Chicago, returning Tue, Jan 13, priced at $139 found 5 days ago

Oak Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sentral Michigan Avenue
4.0-star property

Sentral Michigan Avenue

18.4/10 Exceptional! (983 reviews)

Dec 30 - Jan 1

2 night stay

Philadelphia (PHL) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Philadelphia (PHL)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $570, price is now $375 per person
$375
per person
found 1 day ago
Everything was perfect I will be back in Chicago and will use you guys all the time. Thank you for making my stay amazing and so cozy.

Reviewed on Nov 22, 2025

Cambria Hotel Chicago Loop - Theatre District
4.0-star property

Cambria Hotel Chicago Loop - Theatre District

17.6/10 Exceptional! (1,443 reviews)

Dec 27 - Jan 1

5 night stay

Philadelphia (PHL) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Price was $711, price is now $496 per person
$496
per person
found 11 hours ago
Location is super central, lots of dining locations, close to public transport. Room was clean and great whilst still at an affordable price.

Reviewed on May 22, 2025

Wind Creek Southland Casino and Hotel
4.0-star property

Wind Creek Southland Casino and Hotel

18.8/10 Exceptional! (160 reviews)

Jan 2 - Jan 5

3 night stay

Philadelphia (PHL) to Chicago (MDW)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $607, price is now $425 per person
$425
per person
found 1 day ago
Love the Cleanliness, and no smoking rooms. The staff was excellent! We will attend again

Reviewed on Nov 17, 2025

Don't see what you're looking for?
See all available trips from Philadelphia to Oak Park
View all trips

More About Flying To Oak Park from Philadelphia

Route Information for Flights from Philadelphia to Oak Park

Origin Airport IATA Code
ILG
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Philadelphia to Oak Park

Orbitz On-the-Go is your one-stop shop for discount vacation air travel. Our cutting-edge mobile tools leave you time to pack for the trip. Shop our sales on domestic flights from Philadelphia to Oak Park.

Best Bargains Anywhere

Cheap vacations start at Orbitz On-the-Go. Find the best deals on international flights from Philadelphia to Oak Park.

Complete Travel Planning

Your phone becomes a full-service vacation travel agency with Orbitz mobile phone apps. From reservations to arrivals, every detail is in the palm of your hand. Book budget flights from Philadelphia to Oak Park; add a car and hotel, share your itinerary and keep up with changes. Orbitz apps cover all the bases for you.

Totally Stress-Free

Free Alerts from Orbitz On-the-Go keep your vacation free from worry. Free Alerts updates you the moment any changes occur. You’ll always have the most current flight, gate and baggage claim details. So sit back and enjoy your low fare on Philadelphia to Oak Park flights.

More Miles Faster = Maximum Value

Orbitz On-the-Go securely stores your frequent flier and loyalty program information. Watch your miles add up when you book discount Philadelphia to Oak Park flights with Orbitz. Make your vacation mileage-friendly with low cost air tickets on Philadelphia to Oak Park flights. Orbitz is your destination for vacation value.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.