$50 Cheap flight deals from Princeton (EWR) to Chicago (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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 14
TTN
Mercer
ORD
O'Hare Intl.
$278 Roundtrip, found 8 hours ago
$278
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Mercer to O'Hare Intl., returning Mon, Jul 14, priced at $278 found 8 hours ago
Fri, Jul 11 - Mon, Jul 14
TTN
Mercer
MDW
Midway Intl.
$289 Roundtrip, found 3 days ago
$289
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jul 11 from Mercer to Midway Intl., returning Mon, Jul 14, priced at $289 found 3 days ago
Sat, Jul 12 - Sat, Jul 19
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$320 Roundtrip, found 2 hours ago
$320
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Jul 12 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Jul 19, priced at $320 found 2 hours ago
Fri, Jul 11 - Tue, Jul 29
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$359 Roundtrip, just found
$359
Roundtrip
just found
Select Delta flight, departing Fri, Jul 11 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Jul 29, priced at $359 just found

Airfares from $50 One Way, $100 Round Trip from Princeton to Chicago

Prices starting at $100 for return flights and $50 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, Oct 18 - Sat, Oct 25
EWR
New York
ORD
Chicago
$100 Roundtrip, found 4 hours ago
$100
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Oct 18 from New York to Chicago, returning Sat, Oct 25, priced at $100 found 4 hours ago
Sat, Nov 1 - Tue, Nov 11
EWR
New York
ORD
Chicago
$116 Roundtrip, found 2 hours ago
$116
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Nov 1 from New York to Chicago, returning Tue, Nov 11, priced at $116 found 2 hours ago
Sat, Oct 18 - Sat, Oct 25
EWR
New York
ORD
Chicago
$126 Roundtrip, found 4 hours ago
$126
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Oct 18 from New York to Chicago, returning Sat, Oct 25, priced at $126 found 4 hours ago
Sun, Oct 26 - Tue, Oct 28
EWR
New York
ORD
Chicago
$130 Roundtrip, found 6 hours ago
$130
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Sun, Oct 26 from New York to Chicago, returning Tue, Oct 28, priced at $130 found 6 hours ago
Fri, Sep 19 - Sun, Sep 21
EWR
New York
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select United flight, departing Fri, Sep 19 from New York to Chicago, returning Sun, Sep 21, priced at $137 just found

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,097 reviews)

Aug 30 - Sep 3

4 night stay

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

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Wonderful boutique hotel in excellent Fulton Market area. Walkable to excellent dining and shopping options. The staff were all very friendly and efficient and we loved the convenience of the attached coffee shop.

Reviewed on Jun 14, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,002 reviews)

Aug 8 - Aug 13

5 night stay

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

Spirit Airlines • Non-stop • Coach

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

American Airlines • Non-stop • 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

LondonHouse Chicago, Curio Collection by Hilton
4.5-star property

LondonHouse Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (3,353 reviews)

Aug 28 - Sep 1

4 night stay

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

United • Coach

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

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!

Reviewed on Jun 15, 2025

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

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
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 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
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 24 - Aug 27

3 night stay

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

Delta • Non-stop roundtrip • PremiumEconomy
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

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, Alaska Airlines, Air Canada, Emirates, ANA, TAP Air Portugal, Air New Zealand, United Airlines, British Airways
Earliest Flight Arrival
11:38AM UTC
Latest Flight Arrival
3:41AM UTC

Princeton to Chicago

For the best travel experience from Princeton to Chicago domestic and international travelers everywhere choose Orbitz for guaranteed low prices and cutting-edge mobile tools.

Convenient Low-Cost Travel

Orbitz makes it simple to book discount flights from Princeton to {destination.name} without compromising your schedule. You can always find deals on domestic flights from a location near you. You may find the best deals to fit your schedule by mixing and matching airlines to get you from Princeton to Chicago.

Access Orbitz On The Move

You can access Orbitz anywhere at anytime for travel from Princeton to Chicago using the latest technology. Via your mobile phone you can track any changes to your flight status, gate and baggage claim details, and with Orbitz’s full-service mobile apps for iPhone and Android you can view these trip details anytime anywhere. You can also get fare alerts and travel updates to keep you informed of the cheapest flights from Princeton to Chicago.

Earn Rewards on Your Princeton to Chicago Flights

At Orbitz you can benefit from low cost travel and have your loyalty rewarded on certain types of Princeton to Chicago flights. All you need to do is enter you frequent flyer number when booking and rack up your rewards through Orbitz online on the Traveler Information page for use on future flights. You can even add your frequent flyer number to an existing reservation to start the ball rolling.

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.