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Fares from $28 One Way, $43 Round Trip from Chicago to St. Augustine

Prices starting at $43 for return flights and $28 for one-way flights to St. Augustine were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Need A Hotel In St. Augustine?

Hotels In Top St. Augustine Neighborhoods

Vilano Beach
205 hotels


The Bayfront Inn

2.0 out of 5.0


Old Town
11 hotels

Marion Motor Lodge

2.5 out of 5.0


Stay Near Exciting St. Augustine Attractions

More About Flying To St. Augustine from Chicago

Route Information for Flights from Chicago to St. Augustine

Origin Airport IATA CodeCHI
Destination Airport IATA CodeJAX
Distance1006 mi
Direct Flight AirlinesAmerican Airlines, Alaska Airlines, Air Canada, Frontier Airlines, SAS, Copa Airlines, ANA, Lufthansa, Air New Zealand, United Airlines, Spirit Airlines
Earliest Flight Arrival2:59PM UTC
Latest Flight Arrival10:13PM UTC

Flights Review

Feb 3, 2020

Stuwart s were helpful

Nov 25, 2019

Free water and soda .Good lawd. Stop nickle and diming people to death and make all inclusive . It looks tacky.

Jan 28, 2019

Your planes and staff are phenomenal !!

Sep 16, 2018

On time and friendly staff

Sep 13, 2018

The flight was delayed by an hour.

Apr 17, 2018

Ext trip I will watch out for economy flight which restricted luggage, etc and will avoid flying on that aircraft. Even T window seat there was no room to move

Jan 19, 2018

Slight delay at connection in Chicago, but was to my advantage since gates were a very long ways apart. ( different terminals also )

Chicago to St. Augustine

Orbitz is your one-stop source for great online deals on {} to St. Augustine flights. With our cutting-edge mobile tools and low fares, you are never far from finding fantastic savings on flights from Chicago to St. Augustine.

Unbeatable Deals for Flights From Chicago to St. Augustine

If you are looking for the cheapest {} to St. Augustine flights, you can save your money and your sanity by booking your air fare through Orbitz. Our low price guarantee for international and domestic flights leaves more money in your wallet to spend on activities, restaurants, attractions, and other adventures in your destination.

Book Cheap Chicago to St. Augustine Flights Anytime

There is no need to hover by your computer for the latest air ticket deals—our free mobile apps keep you informed. Find discount air fare and accommodations, research your destination, and buy bargain flights from Chicago to St. Augustine on your Android device, iPad, or iPhone. Stay updated about any updates, disruptions, and delays to your flight by signing up for instant email or text alerts

Don't Miss Out on Frequent Flyer Points

You can still earn points or miles for your frequent flyer program when you take advantage of our low fare Chicago to St. Augustine flights. When you book through Orbitz, you just need to provide your frequent flyer details to get credit for qualifying flights.

Easy Flight Cancellation

In most cases, you can cancel flights from Chicago to St. Augustine online with the same ease as you booked them.

Flights from Chicago to St. Augustine - Frequently Asked Questions

What airlines fly from Chicago to St. Augustine most frequently?
If I am not able to travel due to COVID-19, can I cancel my flight to St. Augustine?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to St. Augustine have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to St. Augustine with flexible change policies?

In most cases you'll have the option to reschedule your flight to St. Augustine without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

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 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. 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 the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.