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Cheap flights from Pennsylvania to Chicago from $43

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 1/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:03 am - 1:03 pm
JFK
-
ORD
3h 00mnonstop
Frontier Logo
6:40 am - 10:04 am
ORD
-
JFK
2h 24mnonstop
$83Frontier
vie., feb. 20 - dom., feb. 22
Spirit Airlines Logo
7:30 am - 9:12 am
LGA
-
ORD
2h 42mnonstop
Spirit Airlines Logo
5:53 pm - 8:59 pm
ORD
-
LGA
2h 06mnonstop
$83Spirit Airlines
jue., ene. 8 - sáb., ene. 10
Multiple Airlines Logo
4:45 pm - 6:25 pm
PHL
-
ORD
2h 40mnonstop
Multiple Airlines Logo
10:48 am - 10:03 pm
ORD
-
PHL
10h 15m1 stop
$99Multiple Airlines
mar., ene. 13 - mié., ene. 14
Multiple Airlines Logo
5:30 am - 5:52 pm
PHL
-
ORD
13h 22m1 stop
Multiple Airlines Logo
7:35 pm - 10:50 pm
ORD
-
PHL
2h 15mnonstop
$101Multiple Airlines
jue., ene. 15 - dom., ene. 18
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
Southwest Logo
7:15 pm - 10:20 pm
MDW
-
LGA
2h 05mnonstop
$139Southwest
jue., ene. 15 - dom., ene. 18
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
Southwest Logo
7:15 pm - 10:20 pm
MDW
-
LGA
2h 05mnonstop
$148Southwest
vie., ene. 16 - mar., ene. 20
JetBlue Logo
1:00 pm - 5:43 pm
DCA
-
ORD
5h 43m1 stop
JetBlue Logo
7:45 am - 2:29 pm
ORD
-
DCA
5h 44m1 stop
$172JetBlue
jue., ene. 15 - dom., ene. 18
JetBlue Logo
1:00 pm - 5:43 pm
DCA
-
ORD
5h 43m1 stop
JetBlue Logo
8:29 am - 2:29 pm
ORD
-
DCA
5h 00m1 stop
$174JetBlue
lun., ene. 26 - lun., feb. 2
United Airlines Logo
7:00 am - 7:51 am
PIT
-
ORD
1h 51mnonstop
United Airlines Logo
9:05 pm - 11:44 pm
ORD
-
PIT
1h 39mnonstop
$203United Airlines
jue., ene. 15 - dom., ene. 18
United Airlines Logo
7:00 am - 7:51 am
PIT
-
ORD
1h 51mnonstop
United Airlines Logo
6:04 pm - 8:41 pm
ORD
-
PIT
1h 37mnonstop
$204United Airlines
sáb., ene. 17 - mié., ene. 21

JetBlue flights from Pennsylvania to Chicago

Our best JetBlue deals on Pennsylvania to Chicago flight tickets
JetBlue
Jan 13
JFK5:25 pmNew York John F Kennedy Intl
3h 11m
ORD7:36 pmChicago O'Hare Intl
Jan 20
ORD9:40 amChicago O'Hare Intl
2h 16m
JFK12:56 pmNew York John F Kennedy Intl
$135
Find similar
JetBlue
Jan 22
JFK11:00 amNew York John F Kennedy Intl
7h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jan 25
ORD7:45 amChicago O'Hare Intl
4h 48m
1 stop
JFK1:33 pmNew York John F Kennedy Intl
$137
Find similar
JetBlue
Jan 22
JFK11:00 amNew York John F Kennedy Intl
7h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jan 25
ORD7:45 amChicago O'Hare Intl
4h 48m
1 stop
JFK1:33 pmNew York John F Kennedy Intl
$138
Find similar

Frontier flights from Pennsylvania to Chicago

Our best Frontier deals on Pennsylvania to Chicago flight tickets
Frontier
Feb 20
JFK11:03 amNew York John F Kennedy Intl
3h 00m
ORD1:03 pmChicago O'Hare Intl
Feb 22
ORD6:40 amChicago O'Hare Intl
2h 24m
JFK10:04 amNew York John F Kennedy Intl
$83
Find similar
Frontier
Feb 22
JFK11:03 amNew York John F Kennedy Intl
3h 00m
ORD1:03 pmChicago O'Hare Intl
Feb 27
ORD6:40 amChicago O'Hare Intl
2h 24m
JFK10:04 amNew York John F Kennedy Intl
$84
Find similar
Frontier
Jan 9
JFK1:00 pmNew York John F Kennedy Intl
2h 57m
ORD2:57 pmChicago O'Hare Intl
Jan 16
ORD12:00 pmChicago O'Hare Intl
2h 24m
JFK3:24 pmNew York John F Kennedy Intl
$85
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 diciembre 14, 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

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

vie. 2/20

11:03 am-1:03 pm

Nonstop3h 00m

Chicago O'Hare Intl

dom. 2/22

6:40 am-10:04 am

Nonstop2h 24m

$83

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

jue. 1/8

7:30 am-9:12 am

Nonstop2h 42m

Chicago O'Hare Intl

sáb. 1/10

5:53 pm-8:59 pm

Nonstop2h 06m

$83

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

mar. 1/13

4:45 pm-6:25 pm

Nonstop2h 40m

Chicago O'Hare Intl

mié. 1/14

10:48 am-10:03 pm

1 stop10h 15m

$99

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

jue. 1/15

5:30 am-5:52 pm

1 stop13h 22m

Chicago O'Hare Intl

dom. 1/18

7:35 pm-10:50 pm

Nonstop2h 15m

$101

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 1/15

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

dom. 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

vie. 1/16

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

mar. 1/20

7:15 pm-10:20 pm

Nonstop2h 05m

$148

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

jue. 1/15

1:00 pm-5:43 pm

1 stop5h 43m

Chicago O'Hare Intl

dom. 1/18

7:45 am-2:29 pm

1 stop5h 44m

$172

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

lun. 1/26

1:00 pm-5:43 pm

1 stop5h 43m

Chicago O'Hare Intl

lun. 2/2

8:29 am-2:29 pm

1 stop5h 00m

$174

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

jue. 1/15

7:00 am-7:51 am

Nonstop1h 51m

Chicago O'Hare Intl

dom. 1/18

9:05 pm-11:44 pm

Nonstop1h 39m

$203

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

sáb. 1/17

7:00 am-7:51 am

Nonstop1h 51m

Chicago O'Hare Intl

mié. 1/21

6:04 pm-8:41 pm

Nonstop1h 37m

$204

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 $193. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from Pennsylvania to Chicago during November average around $207.

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 $328. 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 $493.

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 $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $411.

What is the cheapest Pennsylvania to Chicago flight route?

Fly from Philadelphia to Chicago O'Hare Intl 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 $283 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 $220 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

$166

Fastest flight time

1h 25m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Pennsylvania in the past 72 hours is $166. The best round-trip flight deal from Pennsylvania to Chicago found on momondo in the last 72 hours is $227.
The fastest flight from Pennsylvania to Chicago takes 1h 25m
Direct flights go from Pennsylvania to Chicago every day.
There are 3 airports in Chicago. From Pennsylvania there are direct flights to Chicago O'Hare Intl (ORD).
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 $77Free CancellationRating
5.8
3,081 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $83Free CancellationRating
6.3
8,184 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $92Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
United AirlinesPriceFrom $106Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights
DeltaPriceFrom $118Free CancellationRating
7.9
8,007 reviews
Search Delta 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