Cheap Flights from Chicago (ORD) to St. Augustine (UST)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to St. Augustine, FL (UST-Northeast Florida Regional)

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Flights from Chicago (ORD) to St. Augustine (UST)
Origin airport
O'Hare Intl.
Destination airport
Northeast Florida Regional
Distance
906 mi

Chicago to St. Augustine Flights

The cheapest times to fly from Chicago to St. Augustine

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 Chicago to St. Augustine are during the month of . You can find some of the cheapest flights from Chicago to St. Augustine with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to St. Augustine

Sunday is one of the best days to book for cheap flights from Chicago to St. Augustine: 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 Chicago to St. Augustine

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 Chicago to St. Augustine 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 Chicago to St. Augustine 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 Chicago to St. Augustine 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 ORD to UST last minute?
Booking your trip from O’Hare Intl. Airport (ORD) to Northeast Florida Regional Airport at the last minute could help you save if you’re lucky enough to find a good deal. However, tickets usually don’t drop in price closer to the departure date. If you procrastinate, flights could also be booked up or the best seats taken (we hope you like the middle seat!). If you’d rather not take any chances, book well ahead of the date you want to leave. Don’t forget that some of the biggest bargains can be found up to 12 months in advance. If your favorite airline hasn’t released its fares yet, check back regularly as offers are updated on Expedia constantly.
What airports do you fly into for St. Augustine from Chicago?
Northeast Florida Regional Airport (UST), Jacksonville Intl. Airport (JAX) and Daytona Beach Intl. Airport (DAB) are your options when jetting off from Chicago to St. Augustine. About 5 mi northwest of downtown St. Augustine, Northeast Florida Regional Airport (UST) is the city’s major gateway. Keep in mind things such as flight departure and arrival times and the distance to your hotel before picking your airport. Flagler College and Ponce de Leon’s Fountain of Youth Archaeological Park are a couple of terrific attractions to check out when you get to your destination.
Can I change the date of my flight from ORD to Northeast Florida Regional Airport?
It’s so easy to make amendments to your ORD to Northeast Florida Regional Airport (UST) trip yourself. Access your itinerary via the Expedia Trips portal and tap “change flight.” Look around for new flights and book the one that better fits your plans. You’ll see an estimate of your flight change fee, if applicable. You can also use our Customer Service portal to connect with our Virtual Agent and get answers to your questions.

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