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.

Fri, Jun 2
MDW
Midway Intl.
MCO
Orlando Intl.
$118 One way, found 13 hours ago
$118
One way
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Jun 2 from Midway Intl. to Orlando Intl., priced at $118 found 13 hours ago
Fri, Jun 2 - Wed, Jun 7
MDW
Midway Intl.
MCO
Orlando Intl.
$118 Roundtrip, found 13 hours ago
$118
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Jun 2 from Midway Intl. to Orlando Intl., returning Wed, Jun 7, priced at $118 found 13 hours ago
Sat, Jun 3
ORD
O'Hare Intl.
MCO
Orlando Intl.
$213 One way, just found
$213
One way
just found
Select Frontier Airlines flight, departing Sat, Jun 3 from O'Hare Intl. to Orlando Intl., priced at $213 just found
Sat, Jun 3 - Fri, Jun 9
ORD
O'Hare Intl.
MCO
Orlando Intl.
$213 Roundtrip, just found
$213
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jun 3 from O'Hare Intl. to Orlando Intl., returning Fri, Jun 9, priced at $213 just found
Sat, Jun 3
ORD
O'Hare Intl.
DAB
Daytona Beach Intl.
$406 One way, found 5 days ago
$406
One way
found 5 days ago
Select Delta flight, departing Sat, Jun 3 from O'Hare Intl. to Daytona Beach Intl., priced at $406 found 5 days ago
Sat, Jun 3 - Mon, Jun 12
ORD
O'Hare Intl.
DAB
Daytona Beach Intl.
$406 Roundtrip, found 5 days ago
$406
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jun 3 from O'Hare Intl. to Daytona Beach Intl., returning Mon, Jun 12, priced at $406 found 5 days ago
Sat, Jun 3 - Wed, Jun 14
MDW
Midway Intl.
DAB
Daytona Beach Intl.
$416 Roundtrip, just found
$416
Roundtrip
just found
Select Delta flight, departing Sat, Jun 3 from Midway Intl. to Daytona Beach Intl., returning Wed, Jun 14, priced at $416 just found

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.

Tue, Jul 11
MDW
Chicago
MCO
Orlando
$43 One way, found 2 days ago
$43
One way
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 11 from Chicago to Orlando, priced at $43 found 2 days ago
Wed, Jul 19
ORD
Chicago
MCO
Orlando
$54 One way, just found
$54
One way
just found
Select Frontier Airlines flight, departing Wed, Jul 19 from Chicago to Orlando, priced at $54 just found
Wed, Jun 14
ORD
Chicago
MCO
Orlando
$72 One way, just found
$72
One way
just found
Select Spirit Airlines flight, departing Wed, Jun 14 from Chicago to Orlando, priced at $72 just found
Tue, Jul 11 - Tue, Jul 18
MDW
Chicago
MCO
Orlando
$86 Roundtrip, found 3 days ago
$86
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Jul 11 from Chicago to Orlando, returning Tue, Jul 18, priced at $86 found 3 days ago
Wed, Aug 23
ORD
Chicago
JAX
Jacksonville
$92 One way, found 1 day ago
$92
One way
found 1 day ago
Select JetBlue Airways flight, departing Wed, Aug 23 from Chicago to Jacksonville, priced at $92 found 1 day ago
Tue, Jul 18
ORD
Chicago
MCO
Orlando
$100 One way, just found
$100
One way
just found
Select Delta flight, departing Tue, Jul 18 from Chicago to Orlando, priced at $100 just found
Wed, Aug 2 - Wed, Aug 9
ORD
Chicago
MCO
Orlando
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Aug 2 from Chicago to Orlando, returning Wed, Aug 9, priced at $108 just found
Wed, Jun 14 - Wed, Jun 21
ORD
Chicago
MCO
Orlando
$126 Roundtrip, just found
$126
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jun 14 from Chicago to Orlando, returning Wed, Jun 21, priced at $126 just found
Wed, Aug 23 - Wed, Aug 30
ORD
Chicago
MCO
Orlando
$178 Roundtrip, found 4 hours ago
$178
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Aug 23 from Chicago to Orlando, returning Wed, Aug 30, priced at $178 found 4 hours ago
Mon, Oct 9 - Tue, Oct 10
ORD
Chicago
MCO
Orlando
$193 Roundtrip, found 6 days ago
$193
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Oct 9 from Chicago to Orlando, returning Tue, Oct 10, priced at $193 found 6 days ago

St. Augustine economy flight packages

Westgate Palace a Two Bedroom Condo Resort
4.0-star property

Westgate Palace a Two Bedroom Condo Resort

8/10 Very Good! (1,005 reviews)

Jul 14 - Jul 18

4 night stay

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flightPrice was $902, price is now $570 per person
per person
Nice place, clean quiet with a good pool.

Reviewed on Mar 29, 2023

Liki Tiki Village
3.5-star property

Liki Tiki Village

8.2/10 Very Good! (3,019 reviews)

Jun 30 - Jul 5

5 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Price was $645, price is now $474 per person
per person
Close proximity to activities and family in the area

Reviewed on May 11, 2023

ette hotel
4.0-star property

ette hotel

10/10 Exceptional! (10 reviews)

Jun 30 - Jul 5

5 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flightPrice was $1,194, price is now $889 per person
per person
Just wasn't for us. A very snooty place. Everything is an upcharge. Meanwhile, when I got there at 5pm, my room wasn't ready. I went out for several hours and got back at 10pm. Room still wasn't ready. Just all around disorganized. If you get your kicks from feeling like a rich person, Ette is the place for you. I don't, and was happy when our stay ended.

Reviewed on Feb 26, 2023

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
3.0-star property

Courtyard by Marriott Orlando South/Grande Lakes Area

9.2/10 Wonderful! (1,050 reviews)

Jul 20 - Jul 23

3 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $925, price is now $830 per person
per person
Hotel is very accessible. Front desk person late night was not very guest oriented.

Reviewed on Jun 16, 2022

Holiday Inn Express Orlando - South Park, an IHG Hotel
2.5-star property

Holiday Inn Express Orlando - South Park, an IHG Hotel

8.8/10 Excellent! (158 reviews)

Jul 20 - Jul 23

3 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $848, price is now $768 per person
per person
Lived up to my expectations of holiday inn. Our room and bathroom was extremely clean. The bed was very comfortable. Breakfast as always was a plus. Fred and Farrah(i think is her name) who works the 3-11 shift was so very pleasant and accomodating. Gabriel who checked us out the next morning was equally as pleasant. Well be my go to when I'm in Orlando. Very nice area of town

Reviewed on May 23, 2023

Holiday Inn Express Orlando International Airport, an IHG Hotel
2.5-star property

Holiday Inn Express Orlando International Airport, an IHG Hotel

8.8/10 Excellent! (1,076 reviews)

Jul 20 - Jul 23

3 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $756, price is now $694 per person
per person
Excellent service, very clean and make our stay more comfortable

Reviewed on Apr 15, 2023

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.