$29 Cheap flight deals from Chicago (CHI) to St. Augustine (JAX)

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This Weekend's Flight Deals from Chicago to St. Augustine

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.

Airfares from $29 One Way, $58 Round Trip from Chicago to St. Augustine

Prices starting at $58 for return flights and $29 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.

St. Augustine economy flight packages

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Palazzo Lakeside Hotel
Westgate Palace Hotel / Universal / I-Drive
Westgate Town Center Resort
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St. Augustine packages with premium economy flights

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Mai Hana Hotel - International Drive
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Villatel Orlando Resort
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St. Augustine first class flight packages

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Cedar Lodge on Honey Creek
Hampton Inn & Suites Jekyll Island
Home2 Suites by Hilton Jekyll Island
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More About Flying To St. Augustine from Chicago

Route Information for Flights from Chicago to St. Augustine

Origin Airport IATA Code
CHI
Destination Airport IATA Code
JAX
Distance
1006 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Azul, Copa Airlines, Swiss, Air New Zealand, United Airlines, Alaska Airlines, Frontier Airlines, Southwest Airlines, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, British Airways
Earliest Flight Arrival
1:15PM UTC
Latest Flight Arrival
2:51AM UTC

Chicago to St. Augustine

Orbitz is your one-stop source for great online deals on {origin.name} 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 {origin.name} 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

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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.

Frequently asked questions

Are there non-stop flights from Chicago to St. Augustine?
Yes, you can book direct flights from O’Hare Airport to Orlando Intl. Airport (MCO). What’s more, there are 5 airlines to pick from. Pretty neat, huh? Find out which of these reputable carriers ticks all your boxes:

  • United Airlines
  • American Airlines
  • Spirit Airlines
  • Southwest Airlines
  • Frontier Airlines

What is the shortest flight from Chicago to St. Augustine?
If conditions are good and all goes as scheduled, you could be flying into Jacksonville Intl. Airport from Midway Intl. Airport (MDW) in only 2 hours and 42 minutes. With such a speedy flight time, think about taking just carry-on luggage.
What airlines fly from Chicago to St. Augustine most frequently?
Below are the airlines that frequently fly between Chicago, IL (ORD-O’Hare Intl.) to Orlando, FL (MCO-Orlando Intl.). Whatever you look for in a carrier, you’ll find one that suits your travel plans among these: United Airlines - (UA) with 143 flights every month American Airlines - (AA) with 112 flights every month Spirit Airlines - (NK) with 60 flights every month Southwest Airlines - (WN) with 39 flights every month
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.