$28 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, May 17 - Mon, May 19
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$232 Roundtrip, found 6 days ago
$232
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, May 17 from Newark Liberty Intl. Airport to Midway Intl., returning Mon, May 19, priced at $232 found 6 days ago
Sun, May 18 - Thu, May 22
TTN
Mercer
MDW
Midway Intl.
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 18 from Mercer to Midway Intl., returning Thu, May 22, priced at $232 found 1 day ago
Sat, May 17 - Thu, May 22
TTN
Mercer
ORD
O'Hare Intl.
$242 Roundtrip, found 6 days ago
$242
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 17 from Mercer to O'Hare Intl., returning Thu, May 22, priced at $242 found 6 days ago
Sun, May 18 - Fri, May 23
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$288 Roundtrip, just found
$288
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, May 18 from Newark Liberty Intl. Airport to O'Hare Intl., returning Fri, May 23, priced at $288 just found

Airfares from $28 One Way, $57 Round Trip from Princeton to Chicago

Prices starting at $57 for return flights and $28 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.

Wed, Jun 11 - Sat, Jun 14
EWR
New York
ORD
Chicago
$57 Roundtrip, just found
$57
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jun 11 from New York to Chicago, returning Sat, Jun 14, priced at $57 just found
Wed, Jun 4 - Tue, Jun 10
EWR
New York
ORD
Chicago
$68 Roundtrip, found 3 hours ago
$68
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Wed, Jun 4 from New York to Chicago, returning Tue, Jun 10, priced at $68 found 3 hours ago
Wed, Jun 18 - Sat, Jun 21
EWR
New York
ORD
Chicago
$68 Roundtrip, found 2 hours ago
$68
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Jun 18 from New York to Chicago, returning Sat, Jun 21, priced at $68 found 2 hours ago
Sat, Jun 14 - Tue, Jun 17
EWR
New York
ORD
Chicago
$76 Roundtrip, just found
$76
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jun 14 from New York to Chicago, returning Tue, Jun 17, priced at $76 just found
Sat, Aug 16 - Tue, Aug 19
EWR
New York
ORD
Chicago
$137 Roundtrip, found 3 hours ago
$137
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Aug 16 from New York to Chicago, returning Tue, Aug 19, priced at $137 found 3 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites
3.5-star property

Hilton Chicago/Magnificent Mile Suites

8.8/10 Excellent! (2,064 reviews)

Jul 10 - Jul 13

3 night stay

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

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
I enjoyed my stay at this hotel. The room was clean and the bed comfortable. The hotel restaurant is a definite plus as well.

Reviewed on May 6, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jul 10 - Jul 13

3 night stay

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

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
3.5-star property

Hilton Grand Vacations Club Chicago Magnificent Mile

9.4/10 Exceptional! (231 reviews)

Jul 11 - Jul 14

3 night stay

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

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
close to everything we will be staying here again on our next vacation to Chicago

Reviewed on Aug 31, 2024

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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
716 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Alaska Airlines, Air Canada, Emirates, ANA, TAP Air Portugal, Air New Zealand, United Airlines, Spirit Airlines, British Airways
Earliest Flight Arrival
11:27AM UTC
Latest Flight Arrival
2:12AM UTC

Princeton to Chicago

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Orbitz Makes It Easy to Plan Your Trips on a Budget

You can always find affordable flights from Princeton to Chicago on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.

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.