Cheap Flight Deals From Chicago (CHI) to St. Augustine (JAX) Starting at $43

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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 $43 One Way, $86 Round Trip from Chicago to St. Augustine

Prices starting at $86 for return flights and $43 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

Westgate Palace a Two Bedroom Condo Resort
Liki Tiki Village
ette hotel
Don't see what you're looking for?
See all available trips from Chicago to St. Augustine
View all trips

St. Augustine packages with premium economy flights

Courtyard by Marriott Orlando South/Grande Lakes Area
Holiday Inn Express Orlando - South Park, an IHG Hotel
Holiday Inn Express Orlando International Airport, an IHG Hotel
Don't see what you're looking for?
See all available trips from Chicago to St. Augustine
View all trips

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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to St. Augustine

Smart business means on-the-spot travel planning at budget prices. Orbitz On-the-Go can help by using cutting-edge mobile tools and guaranteed low prices. Orbitz On-the-Go is your go-to for bargain flights from Chicago to St. Augustine, and discount Chicago to St. Augustine flights.

Business Development

Boosting sales with multiple presentations within a day or week? Then easily book cheap domestic flights from Chicago to St. Augustine. Are you expanding into emerging markets? Find low-fare deals on international Chicago to St. Augustine flights. Orbitz On-the-Go mobile apps keep it simple.

Continuing Education

Successful business people know that keeping your edge in business means staying in training. Find a low-cost air ticket for your next workshop with Orbitz flights from Chicago to St. Augustine. Move to the head of the seminar with Orbitz On-the-Go’s guaranteed low prices on Chicago to St. Augustine flights.

Budget Planning

Orbitz allows you to focus on the income, while we reduce your expenses with guaranteed low prices. Your bottom line is bound to improve with our bargain flights from Chicago to St. Augustine and discount Chicago to St. Augustine flights. Watch your business thrive.

Time Management

Time is money, and Orbitz On-the-Go saves both. Our cutting-edge mobile tools make business travel planning quick and easy, even for same-day reservations. It’s not unusual for our clients to save big on same-day tickets for Chicago to {destination.name} flights. Free alerts keep you on time with flight, gate and baggage updates, plus other time-saving features.

Frequently asked questions

Am I able to catch a flight from Chicago to St. Augustine now?
If you’re baffled about quarantine requirements and travel restrictions when flying from Chicago to St. Augustine, go right to our Covid-19 Travel Advisor.
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
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 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.