$87 Cheap flight deals from Princeton (EWR) to Chicago (CHI)

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This Weekend's Flight Deals from Princeton to Chicago

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, Jul 4 - Sat, Jul 11
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jul 4 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Jul 11, priced at $257 just found
Sat, Jul 4 - Tue, Jul 7
TTN
Mercer
ORD
O'Hare Intl.
$297 Roundtrip, found 4 days ago
$297
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Mercer to O'Hare Intl., returning Tue, Jul 7, priced at $297 found 4 days ago
Sat, Jul 4 - Tue, Jul 28
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$302 Roundtrip, found 2 hours ago
$302
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Jul 4 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Jul 28, priced at $302 found 2 hours ago
Fri, Jul 3 - Sat, Jul 11
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$316 Roundtrip, found 1 day ago
$316
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 3 from Newark Liberty Intl. Airport to Greater Rockford, returning Sat, Jul 11, priced at $316 found 1 day ago

Airfares from $87 One Way, $175 Round Trip from Princeton to Chicago

Prices starting at $175 for return flights and $87 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Aug 15 - Tue, Aug 18
EWR
New York
ORD
Chicago
$175 Roundtrip, just found
$175
Roundtrip
just found
Select United flight, departing Sat, Aug 15 from New York to Chicago, returning Tue, Aug 18, priced at $175 just found
Thu, Oct 15 - Tue, Oct 20
EWR
New York
ORD
Chicago
$184 Roundtrip, found 5 hours ago
$184
Roundtrip
found 5 hours ago
Select United flight, departing Thu, Oct 15 from New York to Chicago, returning Tue, Oct 20, priced at $184 found 5 hours ago
Wed, Jul 22 - Wed, Jul 29
EWR
New York
RFD
Rockford
$186 Roundtrip, found 2 days ago
$186
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jul 22 from New York to Rockford, returning Wed, Jul 29, priced at $186 found 2 days ago
Sat, Oct 31 - Tue, Nov 3
EWR
New York
MDW
Chicago
$191 Roundtrip, found 12 hours ago
$191
Roundtrip
found 12 hours ago
Select Delta flight, departing Sat, Oct 31 from New York to Chicago, returning Tue, Nov 3, priced at $191 found 12 hours ago
Wed, Oct 7 - Sat, Oct 24
EWR
New York
ORD
Chicago
$191 Roundtrip, found 12 hours ago
$191
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Oct 7 from New York to Chicago, returning Sat, Oct 24, priced at $191 found 12 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,554 reviews)

Aug 15 - Aug 18

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,039, price is now $726 per person
$726
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly

Reviewed on May 5, 2026

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (1,013 reviews)

Aug 5 - Aug 8

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,139, price is now $825 per person
$825
per person
found 12 hours ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!

Reviewed on Jul 8, 2024

The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

9.4/10 Exceptional! (126 reviews)

Aug 6 - Aug 11

5 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,216, price is now $881 per person
$881
per person
found 1 day ago
Always stay here never anywhere else we love it

Reviewed on Dec 30, 2025

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Chicago first class flight packages

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

9.2/10 Wonderful! (1,821 reviews)

Aug 7 - Aug 9

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,099, price is now $893 per person
$893
per person
found 9 hours ago
The excellent hotel launch our vacation in Chicago. The rooms were modern and comfortable. Did you help?

Reviewed on Jun 12, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (1,899 reviews)

Aug 7 - Aug 9

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,469, price is now $1,218 per person
$1,218
per person
found 9 hours ago
The location was great. The only thing at night there were a line of cars outside that were doing donuts in the street, squalling tires and dancing. The police never did come. Staff was very friendly.

Reviewed on Jun 8, 2026

The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,330 reviews)

Aug 7 - Aug 9

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,119, price is now $932 per person
$932
per person
found 9 hours ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.

Reviewed on Jul 26, 2025

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More About Flying To Chicago from Princeton

Route Information for Flights from Princeton to Chicago

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

Princeton to Chicago

Great Deals on Flights From Princeton to Chicago

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Frequently asked questions

Are there non-stop flights from Princeton to Chicago?
There most certainly are, which is fantastic news if you're not a massive fan of switching planes en route. United Airlines and American Airlines fly straight from Newark Airport to Chicago, IL (ORD-O'Hare Intl.).
What is the shortest flight from Princeton to Chicago?
With the flight from EWR to Chicago, IL (MDW-Midway Intl.) taking a minimum of 3 hours and 3 minutes, there's plenty of time to enjoy the flying experience. Ask for an in-flight wine or two and get cozy in your seat with a book or movie.
What airlines fly from Princeton to Chicago most frequently?
There are two airlines offering the most frequent flights from Newark, NJ (EWR-Liberty Intl.) to Chicago, IL (ORD-O'Hare Intl.), including United Airlines (UA). A top pick for many travelers, it operates 243 flights on this route every month. American Airlines (AA) also flies from Princeton to Chicago. It's another excellent option and offers 104 flights monthly.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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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.