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Cheap flights from Pennsylvania to Chicago from $58

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 5/4. 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
1 adult, Economy, 0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
6:30 am - 8:01 am
LGA
-
ORD
2h 31mnonstop
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
$102Spirit Airlines
Mon, Apr 13 - Fri, Apr 17
Spirit Airlines Logo
2:38 pm - 4:14 pm
LGA
-
ORD
2h 36mnonstop
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
$103Spirit Airlines
Sat, Apr 18 - Mon, Apr 20
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$113Frontier
Fri, Apr 24 - Sun, Apr 26
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$115Frontier
Thu, Apr 30 - Sun, May 3
Multiple Airlines Logo
10:54 pm - 12:22 am
EWR
-
ORD
2h 28mnonstop
Multiple Airlines Logo
6:08 pm - 1:16 am
ORD
-
EWR
6h 08m
1 stop
$121Multiple Airlines
Wed, Apr 8 - Wed, Apr 29
Multiple Airlines Logo
1:00 pm - 7:51 pm
JFK
-
ORD
7h 51m
1 stop
Multiple Airlines Logo
8:35 am - 12:00 pm
ORD
-
JFK
2h 25mnonstop
$150Multiple Airlines
Tue, May 5 - Wed, May 13
JetBlue Logo
6:00 am - 7:41 am
JFK
-
ORD
2h 41mnonstop
JetBlue Logo
8:34 am - 11:59 am
ORD
-
JFK
2h 25mnonstop
$154JetBlue
Tue, May 5 - Wed, May 6
JetBlue Logo
6:00 am - 7:44 am
JFK
-
ORD
2h 44mnonstop
JetBlue Logo
8:35 am - 12:00 pm
ORD
-
JFK
2h 25mnonstop
$157JetBlue
Tue, May 12 - Tue, May 19
Delta Logo
10:24 am - 12:26 pm
JFK
-
ORD
3h 02mnonstop
Delta Logo
1:06 pm - 4:29 pm
ORD
-
JFK
2h 23mnonstop
$159Delta
Tue, Apr 21 - Wed, Apr 29
Delta Logo
8:19 am - 10:28 am
JFK
-
ORD
3h 09mnonstop
Delta Logo
6:04 am - 9:29 am
ORD
-
JFK
2h 25mnonstop
$160Delta
Sat, Apr 18 - Tue, Apr 21

Spirit Airlines flights from Pennsylvania to Chicago

Our best Spirit Airlines deals on Pennsylvania to Chicago flight tickets
Spirit Airlines
Apr 13
LGA6:30 amNew York LaGuardia
2h 31m
ORD8:01 amChicago O'Hare Intl
Apr 16
ORD2:09 pmChicago O'Hare Intl
2h 11m
LGA5:20 pmNew York LaGuardia
$102
Spirit Airlines
Apr 18
LGA2:38 pmNew York LaGuardia
2h 36m
ORD4:14 pmChicago O'Hare Intl
Apr 20
ORD2:09 pmChicago O'Hare Intl
2h 11m
LGA5:20 pmNew York LaGuardia
$103
Spirit Airlines
Apr 13
LGA6:30 amNew York LaGuardia
2h 31m
ORD8:01 amChicago O'Hare Intl
Apr 21
ORD2:09 pmChicago O'Hare Intl
2h 11m
LGA5:20 pmNew York LaGuardia
$105

American Airlines flights from Pennsylvania to Chicago

Our best American Airlines deals on Pennsylvania to Chicago flight tickets
American Airlines
Apr 16
EWR7:10 amNewark
2h 52m
ORD9:02 amChicago O'Hare Intl
Apr 20
ORD1:07 pmChicago O'Hare Intl
2h 23m
EWR4:30 pmNewark
$162
American Airlines
Apr 16
JFK9:03 amNew York John F Kennedy Intl
2h 55m
ORD10:58 amChicago O'Hare Intl
Apr 18
ORD4:27 pmChicago O'Hare Intl
2h 32m
JFK7:59 pmNew York John F Kennedy Intl
$165
American Airlines
May 13
JFK9:03 amNew York John F Kennedy Intl
2h 55m
ORD10:58 amChicago O'Hare Intl
May 16
ORD4:27 pmChicago O'Hare Intl
2h 32m
JFK7:59 pmNew York John F Kennedy Intl
$171

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 March 26, 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

Cheapest round-trip

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 4/13

6:30 am-8:01 am

Nonstop2h 31m

Chicago O'Hare Intl

Fri 4/17

2:09 pm-5:20 pm

Nonstop2h 11m

$102

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 4/18

2:38 pm-4:14 pm

Nonstop2h 36m

Chicago O'Hare Intl

Mon 4/20

2:09 pm-5:20 pm

Nonstop2h 11m

$103
Quickest round-trip

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 4/24

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sun 4/26

7:30 am-10:38 am

Nonstop2h 08m

$113

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 4/30

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sun 5/3

7:30 am-10:38 am

Nonstop2h 08m

$115

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 4/8

10:54 pm-12:22 am

Nonstop2h 28m

Chicago O'Hare Intl

Wed 4/29

6:08 pm-1:16 am

1 stop6h 08m

$121

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 5/5

1:00 pm-7:51 pm

1 stop7h 51m

Chicago O'Hare Intl

Wed 5/13

8:35 am-12:00 pm

Nonstop2h 25m

$150

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 5/5

6:00 am-7:41 am

Nonstop2h 41m

Chicago O'Hare Intl

Wed 5/6

8:34 am-11:59 am

Nonstop2h 25m

$154

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 5/12

6:00 am-7:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Tue 5/19

8:35 am-12:00 pm

Nonstop2h 25m

$157

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 4/21

10:24 am-12:26 pm

Nonstop3h 02m

Chicago O'Hare Intl

Wed 4/29

1:06 pm-4:29 pm

Nonstop2h 23m

$159

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 4/18

8:19 am-10:28 am

Nonstop3h 09m

Chicago O'Hare Intl

Tue 4/21

6:04 am-9:29 am

Nonstop2h 25m

$160

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 January is, on average, the cheapest month to fly to Chicago from Pennsylvania, with most prices found around $188. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Pennsylvania to Chicago during September average around $188.

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 $305. 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 $496.

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 $412.

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 $284 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 $206 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.

  • 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 $76Free CancellationRating
5.7
3,015 reviews
Search Frontier flights
American AirlinesPriceFrom $92Free CancellationRating
7.1
11,499 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,331 reviews
Search Southwest flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,339 reviews
Search Delta flights
United AirlinesPriceFrom $132Free CancellationRating
7.4
9,489 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
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