Cheap Flights from Caldwell (CDW) to Chicago (ORD)

Popular airlines from Caldwell, NJ (CDW-Essex County) to Chicago O'Hare Intl. Airport (ORD)

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Flights from Caldwell (CDW) to Chicago (ORD)
Origin airport
Essex County
Destination airport
O'Hare Intl.
Distance
709 mi

Caldwell to Chicago Flights

The cheapest times to fly from Caldwell to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Caldwell to Chicago are during the month of . You can find some of the cheapest flights from Caldwell to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Caldwell to Chicago

Sunday is one of the best days to book for cheap flights from Caldwell to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Caldwell to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Caldwell to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Caldwell to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Caldwell to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from CDW to ORD by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from CDW to ORD?
The cheapest flights from CDW to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD)?
You can't fly direct from Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD). However, you can easily travel to Chicago without any layovers by leaving from John F. Kennedy Intl. Airport (JFK).
What is the cheapest airline that flies from CDW to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from CDW to ORD. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD)?
You'll have to book a flight with a layover if you're traveling from Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from CDW to ORD?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can vary depending on various factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD) route, fly before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from CDW to ORD are generally more expensive. To lock in the best prices, start searching for flights as early as possible. That being said, if you're flexible with your travel dates, you may score a cheap fare just before your departure.
Is it cheaper to book a CDW to ORD flight and hotel package?
Securing a CDW to ORD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Select from our wide range of stays and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Caldwell, NJ (CDW-Essex County) to O'Hare Intl. Airport (ORD)?
If you reserved your CDW to ORD flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

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*Available to One Key members.