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

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.
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

Is it cheaper to buy a plane ticket from CDW to O'Hare Intl. Airport (ORD) last minute?
Being a spontaneous soul is a great way to travel the globe, but it isn’t always the ideal way to land a cheap airfare. It’s better to book your CDW to O’Hare Intl. Airport (ORD) trip well in advance instead of leaving it to the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. We recommend saving that spontaneity for when you’re discovering O’Hare Intl. Airport (ORD)!
What airports do you fly into for Chicago from Fairfield?
With O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) to select from, journeying from Fairfield to Chicago is no sweat. The city’s key hub, O’Hare Intl. Airport (ORD), is roughly 16 mi northwest of the downtown area. As well as the price of tickets, consider things like train or bus options from the airport and the distance to your hotel when deciding where to fly into. Get your Chicago adventure off to a terrific start by discovering Wrigley Field and Millennium Park.
Can I change the date of my flight from CDW to O'Hare Airport?
It’s so easy to make changes to your CDW to O’Hare Airport trip yourself. Simply go to the Expedia Trips portal and choose “change flight.” Browse around for new flights and secure the one that fits your new plans. You’ll get an estimate of the extra charges, if applicable. You can also use our Customer Service portal to chat to our Virtual Agent and quickly get answers to all your questions.

Explore a world of travel with Expedia

*Available to One Key members.