$66 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 12 - Mon, Jul 21
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$242 Roundtrip, just found
$242
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jul 12 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Jul 21, priced at $242 just found
Sat, Jul 12 - Mon, Jul 14
TTN
Mercer
ORD
O'Hare Intl.
$274 Roundtrip, found 6 days ago
$274
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Mercer to O'Hare Intl., returning Mon, Jul 14, priced at $274 found 6 days ago
Fri, Jul 11 - Mon, Jul 14
TTN
Mercer
MDW
Midway Intl.
$289 Roundtrip, found 2 days ago
$289
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jul 11 from Mercer to Midway Intl., returning Mon, Jul 14, priced at $289 found 2 days ago
Sun, Jul 13 - Wed, Jul 16
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jul 13 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, Jul 16, priced at $310 found 1 day ago

Airfares from $66 One Way, $132 Round Trip from Princeton to Chicago

Prices starting at $132 for return flights and $66 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.

Thu, Oct 16 - Sun, Oct 19
EWR
New York
ORD
Chicago
$132 Roundtrip, just found
$132
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Oct 16 from New York to Chicago, returning Sun, Oct 19, priced at $132 just found
Thu, Jul 24 - Fri, Jul 25
EWR
New York
ORD
Chicago
$143 Roundtrip, found 9 hours ago
$143
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Thu, Jul 24 from New York to Chicago, returning Fri, Jul 25, priced at $143 found 9 hours ago
Wed, Oct 8 - Sat, Oct 11
EWR
New York
ORD
Chicago
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select United flight, departing Wed, Oct 8 from New York to Chicago, returning Sat, Oct 11, priced at $147 found 2 days ago
Sat, Sep 13 - Tue, Sep 16
EWR
New York
ORD
Chicago
$147 Roundtrip, found 21 hours ago
$147
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sat, Sep 13 from New York to Chicago, returning Tue, Sep 16, priced at $147 found 21 hours ago
Wed, Sep 24 - Thu, Sep 25
EWR
New York
MDW
Chicago
$165 Roundtrip, found 2 days ago
$165
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Sep 24 from New York to Chicago, returning Thu, Sep 25, priced at $165 found 2 days ago

Chicago economy flight packages

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

Swissotel - Chicago

8.8/10 Excellent! (2,274 reviews)

Aug 29 - Aug 31

2 night stay

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

United • Roundtrip • Coach
per person
found 1 day ago
Clean and attentive staff

Reviewed on Jun 21, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,623 reviews)

Aug 29 - Aug 31

2 night stay

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

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,002 reviews)

Aug 29 - Aug 31

2 night stay

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

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

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See all available trips from Princeton to Chicago
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Chicago packages with premium economy flights

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

Swissotel - Chicago

8.8/10 Excellent! (2,274 reviews)

Aug 24 - Aug 27

3 night stay

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

Delta • Non-stop roundtrip • PremiumEconomy
per person
just found
Clean and attentive staff

Reviewed on Jun 21, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,623 reviews)

Aug 24 - Aug 27

3 night stay

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

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
per person
just found
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,002 reviews)

Aug 24 - Aug 27

3 night stay

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

Delta • Non-stop roundtrip • PremiumEconomy
per person
just found
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

Don't see what you're looking for?
See all available trips from Princeton to Chicago
View all trips

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
716 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Alaska Airlines, Emirates, ANA, TAP Air Portugal, Air New Zealand, United Airlines, British Airways
Earliest Flight Arrival
11:38AM UTC
Latest Flight Arrival
3:42AM UTC

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.

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.