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Cheap flights from Pennsylvania to Chicago from $56

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 3/3. 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

Enter your travel dates to find the best prices.
Spirit Airlines Logo
7:40 am - 9:22 am
LGA
-
ORD
2h 42mnonstop
Spirit Airlines Logo
5:58 pm - 8:59 pm
ORD
-
LGA
2h 01mnonstop
$87Spirit Airlines
Wed, Feb 18 - Wed, Feb 18
Spirit Airlines Logo
12:02 pm - 7:11 pm
EWR
-
ORD
8h 09m
1 stop
Spirit Airlines Logo
6:51 pm - 10:00 pm
ORD
-
EWR
2h 09mnonstop
$88Spirit Airlines
Wed, Mar 4 - Mon, Mar 9
Frontier Logo
4:29 pm - 6:29 pm
JFK
-
ORD
3h 00mnonstop
Frontier Logo
12:05 pm - 3:29 pm
ORD
-
JFK
2h 24mnonstop
$89Frontier
Wed, Mar 18 - Wed, Mar 25
Multiple Airlines Logo
5:15 am - 10:51 am
EWR
-
ORD
6h 36m
1 stop
Multiple Airlines Logo
6:51 pm - 10:00 pm
ORD
-
EWR
2h 09mnonstop
$89Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
Frontier Logo
4:29 pm - 6:29 pm
JFK
-
ORD
3h 00mnonstop
Frontier Logo
12:05 pm - 3:29 pm
ORD
-
JFK
2h 24mnonstop
$90Frontier
Wed, Mar 18 - Wed, Mar 25
Multiple Airlines Logo
11:04 am - 1:00 pm
JFK
-
ORD
2h 56mnonstop
Multiple Airlines Logo
8:31 am - 11:49 am
ORD
-
JFK
2h 18mnonstop
$97Multiple Airlines
Thu, Apr 23 - Sat, Apr 25
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
Southwest Logo
6:05 pm - 9:10 pm
MDW
-
LGA
2h 05mnonstop
$125Southwest
Sat, Feb 28 - Mon, Mar 2
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
Southwest Logo
6:05 am - 9:10 am
MDW
-
LGA
2h 05mnonstop
$130Southwest
Tue, Feb 24 - Mon, Mar 2
American Airlines Logo
9:35 am - 10:57 am
DCA
-
ORD
2h 22mnonstop
American Airlines Logo
8:58 pm - 11:50 pm
ORD
-
DCA
1h 52mnonstop
$174American Airlines
Wed, Mar 4 - Sat, Mar 7
American Airlines Logo
7:50 pm - 9:15 pm
DCA
-
ORD
2h 25mnonstop
American Airlines Logo
6:08 am - 8:59 am
ORD
-
DCA
1h 51mnonstop
$177American Airlines
Sat, Mar 7 - Sat, Mar 14

Spirit Airlines flights from Pennsylvania to Chicago

Our best Spirit Airlines deals on Pennsylvania to Chicago flight tickets
Spirit Airlines
Feb 18
LGA7:40 amNew York LaGuardia
2h 42m
ORD9:22 amChicago O'Hare Intl
Feb 18
ORD5:58 pmChicago O'Hare Intl
2h 01m
LGA8:59 pmNew York LaGuardia
$87
Spirit Airlines
Mar 4
EWR11:05 pmNewark
2h 35m
ORD12:40 amChicago O'Hare Intl
Mar 8
ORD6:51 pmChicago O'Hare Intl
2h 09m
EWR10:00 pmNewark
$88
Spirit Airlines
Feb 24
LGA4:59 pmNew York LaGuardia
7h 48m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 25
ORD5:58 pmChicago O'Hare Intl
2h 01m
LGA8:59 pmNew York LaGuardia
$89

JetBlue flights from Pennsylvania to Chicago

Our best JetBlue deals on Pennsylvania to Chicago flight tickets
JetBlue
Feb 26
JFK9:50 amNew York John F Kennedy Intl
3h 04m
ORD11:54 amChicago O'Hare Intl
Mar 1
ORD6:04 amChicago O'Hare Intl
2h 16m
JFK9:20 amNew York John F Kennedy Intl
$134
JetBlue
Feb 17
JFK9:25 pmNew York John F Kennedy Intl
3h 01m
ORD11:26 pmChicago O'Hare Intl
Feb 24
ORD6:04 amChicago O'Hare Intl
2h 16m
JFK9:20 amNew York John F Kennedy Intl
$161
JetBlue
Feb 17
JFK9:25 pmNew York John F Kennedy Intl
3h 01m
ORD11:26 pmChicago O'Hare Intl
Feb 23
ORD6:04 amChicago O'Hare Intl
2h 16m
JFK9:20 amNew York John F Kennedy Intl
$162

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 February 3, 2026.
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

LGA - ORD

LGAORD

New York LaGuardia

Wed 2/18

7:40 am-9:22 am

Nonstop2h 42m

Chicago O'Hare Intl

Wed 2/18

5:58 pm-8:59 pm

Nonstop2h 01m

$87

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 3/4

12:02 pm-7:11 pm

1 stop8h 09m

Chicago O'Hare Intl

Mon 3/9

6:51 pm-10:00 pm

Nonstop2h 09m

$88

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 3/18

4:29 pm-6:29 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 3/25

12:05 pm-3:29 pm

Nonstop2h 24m

$89

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 3/3

5:15 am-10:51 am

1 stop6h 36m

Chicago O'Hare Intl

Tue 3/10

6:51 pm-10:00 pm

Nonstop2h 09m

$89

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 3/18

4:29 pm-6:29 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 3/25

12:05 pm-3:29 pm

Nonstop2h 24m

$90

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 4/23

11:04 am-1:00 pm

Nonstop2h 56m

Chicago O'Hare Intl

Sat 4/25

8:31 am-11:49 am

Nonstop2h 18m

$97

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 2/28

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 3/2

6:05 pm-9:10 pm

Nonstop2h 05m

$125

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 2/24

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 3/2

6:05 am-9:10 am

Nonstop2h 05m

$130

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 3/4

9:35 am-10:57 am

Nonstop2h 22m

Chicago O'Hare Intl

Sat 3/7

8:58 pm-11:50 pm

Nonstop1h 52m

$174

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 3/7

7:50 pm-9:15 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sat 3/14

6:08 am-8:59 am

Nonstop1h 51m

$177

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 $315. 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 $417.

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 $286 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 $222 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

$127

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 $127. The best round-trip flight deal from Pennsylvania to Chicago found on momondo in the last 72 hours is $304.
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 $74Free CancellationRating
5.7
3,051 reviews
Search Frontier flights
American AirlinesPriceFrom $92Free CancellationRating
7.2
11,216 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,272 reviews
Search Southwest flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,138 reviews
Search Delta flights
United AirlinesPriceFrom $107Free CancellationRating
7.4
9,236 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
Munster
Crown Point
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