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Cheap flights from Pennsylvania to Chicago from $28

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pennsylvania to Chicago departing on 11/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Frontier Logo
10:21 am - 11:58 amPHL-ORD
2h 37mnonstop
Frontier Logo
6:10 am - 9:25 amORD-PHL
2h 15mnonstop
$54Frontier
Find Deal
Fri, Oct 3 - Mon, Oct 6
Frontier Logo
10:21 am - 11:52 amPHL-ORD
2h 31mnonstop
Frontier Logo
6:20 am - 9:26 amORD-PHL
2h 06mnonstop
$58Frontier
Find Deal
Thu, Oct 23 - Sun, Oct 26
Spirit Airlines Logo
10:59 am - 11:59 pmLGA-ORD
14h 00m1 stop
Spirit Airlines Logo
4:35 pm - 7:41 pmORD-LGA
2h 06mnonstop
$67Spirit Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Spirit Airlines Logo
3:12 pm - 4:50 pmLGA-ORD
2h 38mnonstop
Spirit Airlines Logo
11:13 am - 2:18 pmORD-LGA
2h 05mnonstop
$69Spirit Airlines
Find Deal
Sat, Sep 6 - Mon, Sep 8
JetBlue Logo
8:30 pm - 10:28 pmJFK-ORD
2h 58mnonstop
JetBlue Logo
6:10 am - 9:29 amORD-JFK
2h 19mnonstop
$137JetBlue
Find Deal
Sat, Aug 30 - Wed, Sep 3
Southwest Logo
6:00 am - 7:20 amLGA-MDW
2h 20mnonstop
Southwest Logo
7:05 pm - 10:15 pmMDW-LGA
2h 10mnonstop
$137Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 3
JetBlue Logo
4:30 pm - 6:23 pmJFK-ORD
2h 53mnonstop
JetBlue Logo
6:45 am - 9:59 amORD-JFK
2h 14mnonstop
$141JetBlue
Find Deal
Sat, Sep 6 - Mon, Sep 8
Southwest Logo
9:00 am - 10:25 amLGA-MDW
2h 25mnonstop
Southwest Logo
6:55 am - 9:55 amMDW-LGA
2h 00mnonstop
$142Southwest
Find Deal
Wed, Sep 3 - Sat, Sep 6
United Airlines Logo
7:00 am - 8:38 amEWR-ORD
2h 38mnonstop
United Airlines Logo
1:12 pm - 4:30 pmORD-EWR
2h 18mnonstop
$142United Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 3
United Airlines Logo
7:59 am - 9:37 amEWR-ORD
2h 38mnonstop
United Airlines Logo
7:35 pm - 10:59 pmORD-EWR
2h 24mnonstop
$157United Airlines
Find Deal
Sat, Sep 6 - Mon, Sep 8

Frontier flights from Pennsylvania to Chicago

Our best Frontier deals on Pennsylvania to Chicago flight tickets
Frontier
Oct 3
PHL10:21 amPhiladelphia
2h 37m
ORD11:58 amChicago O'Hare Intl
Oct 6
ORD6:10 amChicago O'Hare Intl
2h 15m
PHL9:25 amPhiladelphia
$54
Find similar
Frontier
Oct 23
PHL10:21 amPhiladelphia
2h 31m
ORD11:52 amChicago O'Hare Intl
Oct 26
ORD6:20 amChicago O'Hare Intl
2h 06m
PHL9:26 amPhiladelphia
$58
Find similar
Frontier
Oct 20
PHL10:21 amPhiladelphia
2h 31m
ORD11:52 amChicago O'Hare Intl
Oct 26
ORD6:20 amChicago O'Hare Intl
2h 06m
PHL9:26 amPhiladelphia
$59
Find similar

Delta flights from Pennsylvania to Chicago

Our best Delta deals on Pennsylvania to Chicago flight tickets
Delta
Sep 13
JFK10:30 amNew York John F Kennedy Intl
2h 46m
ORD12:16 pmChicago O'Hare Intl
Sep 16
ORD6:28 pmChicago O'Hare Intl
2h 40m
JFK10:08 pmNew York John F Kennedy Intl
$147
Find similar
Delta
Sep 6
JFK8:00 amNew York John F Kennedy Intl
2h 55m
ORD9:55 amChicago O'Hare Intl
Sep 8
ORD7:00 amChicago O'Hare Intl
2h 23m
JFK10:23 amNew York John F Kennedy Intl
$157
Find similar
Delta
Sep 6
JFK3:29 pmNew York John F Kennedy Intl
3h 08m
ORD5:37 pmChicago O'Hare Intl
Sep 8
ORD7:00 amChicago O'Hare Intl
2h 23m
JFK10:23 amNew York John F Kennedy Intl
$158
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Pennsylvania to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Pennsylvania to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 10/3

10:21 am-11:58 am

Nonstop2h 37m

Chicago O'Hare Intl

Mon 10/6

6:10 am-9:25 am

Nonstop2h 15m

$54

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 10/23

10:21 am-11:52 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 10/26

6:20 am-9:26 am

Nonstop2h 06m

$58

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 8/30

10:59 am-11:59 pm

1 stop14h 00m

Chicago O'Hare Intl

Sat 9/6

4:35 pm-7:41 pm

Nonstop2h 06m

$67

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 9/6

3:12 pm-4:50 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 9/8

11:13 am-2:18 pm

Nonstop2h 05m

$69

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 8/30

8:30 pm-10:28 pm

Nonstop2h 58m

Chicago O'Hare Intl

Wed 9/3

6:10 am-9:29 am

Nonstop2h 19m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/3

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Wed 9/3

7:05 pm-10:15 pm

Nonstop2h 10m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 9/6

4:30 pm-6:23 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 9/8

6:45 am-9:59 am

Nonstop2h 14m

$141

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/3

9:00 am-10:25 am

Nonstop2h 25m

Chicago Midway

Sat 9/6

6:55 am-9:55 am

Nonstop2h 00m

$142

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 9/3

7:00 am-8:38 am

Nonstop2h 38m

Chicago O'Hare Intl

Wed 9/3

1:12 pm-4:30 pm

Nonstop2h 18m

$142

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 9/6

7:59 am-9:37 am

Nonstop2h 38m

Chicago O'Hare Intl

Mon 9/8

7:35 pm-10:59 pm

Nonstop2h 24m

$157

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Pennsylvania to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Pennsylvania, with most prices found around $129. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Pennsylvania to Chicago during August average around $177.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $306. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Pennsylvania to Chicago for around $458.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pennsylvania to Chicago during this time can be as low as $229. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $383.

What is the cheapest Pennsylvania to Chicago flight route?

Fly from Pittsburgh to Chicago Midway for the best Pennsylvania - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Pennsylvania when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $274 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Pennsylvania for as low as $212 on momondo.

What cabin class options are available on Pennsylvania to Chicago flights?

There are 4 cabin classes available to choose from on Pennsylvania to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Pennsylvania to Chicago flights?

No. A direct flight is the cheapest option for a flight between Pennsylvania to Chicago.

Cheap Pennsylvania to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pennsylvania to Chicago

Best Price Found

$28

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Pennsylvania in the past 72 hours is $28. The best round-trip flight deal from Pennsylvania to Chicago found on momondo in the last 72 hours is $54.
The fastest flight from Pennsylvania to Chicago takes 2h 05m
Direct flights go from Pennsylvania to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • When did momondo last update prices for flights from Pennsylvania to Chicago?

    Prices for flights from Pennsylvania to Chicago were last updated today.

  • How many operators does momondo search for flights from Pennsylvania to Chicago?

  • How old do you have to be to fly from Pennsylvania to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Pennsylvania to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Pennsylvania to Chicago?

Best airlines flying from Pennsylvania to Chicago

Compare and see reviews for airlines that fly from Pennsylvania to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $52Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
American AirlinesPriceFrom $97Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $118Free CancellationRating
8.0
7,981 reviews
Search Delta flights
SouthwestPriceFrom $126Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Pennsylvania to Chicago?

It is quick and easy to find Pennsylvania to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Pennsylvania to Chicago with flexible booking policies on momondo?

All flight searches from Pennsylvania to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Pennsylvania to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Pennsylvania.

I’m not ready to book a flight from Pennsylvania to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Pennsylvania are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport