$27 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.

Sun, Apr 21 - Thu, Apr 25
MDW
Midway Intl.
MCO
Orlando Intl.
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 21 from Midway Intl. to Orlando Intl., returning Thu, Apr 25, priced at $144 found 1 day ago
Sat, Apr 20 - Wed, Apr 24
ORD
O'Hare Intl.
MCO
Orlando Intl.
$175 Roundtrip, just found
$175
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Apr 20 from O'Hare Intl. to Orlando Intl., returning Wed, Apr 24, priced at $175 just found
Fri, Apr 19 - Mon, Apr 22
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$449 Roundtrip, found 22 hours ago
$449
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Fri, Apr 19 from O'Hare Intl. to Jacksonville Intl., returning Mon, Apr 22, priced at $449 found 22 hours ago
Sat, Apr 20 - Wed, May 8
ORD
O'Hare Intl.
DAB
Daytona Beach Intl.
$468 Roundtrip, found 5 days ago
$468
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Apr 20 from O'Hare Intl. to Daytona Beach Intl., returning Wed, May 8, priced at $468 found 5 days ago

Airfares from $27 One Way, $53 Round Trip from Chicago to St. Augustine

Prices starting at $53 for return flights and $27 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.

Wed, May 15 - Wed, May 22
ORD
Chicago
MCO
Orlando
$53 Roundtrip, just found
$53
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, May 15 from Chicago to Orlando, returning Wed, May 22, priced at $53 just found
Tue, May 7 - Tue, May 14
ORD
Chicago
MCO
Orlando
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, May 7 from Chicago to Orlando, returning Tue, May 14, priced at $74 just found
Mon, May 13 - Wed, May 22
MDW
Chicago
MCO
Orlando
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, May 13 from Chicago to Orlando, returning Wed, May 22, priced at $78 just found
Sat, May 4 - Sat, May 18
MDW
Chicago
JAX
Jacksonville
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 4 from Chicago to Jacksonville, returning Sat, May 18, priced at $108 just found
Wed, Jun 26 - Sat, Jun 29
ORD
Chicago
JAX
Jacksonville
$170 Roundtrip, found 6 days ago
$170
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jun 26 from Chicago to Jacksonville, returning Sat, Jun 29, priced at $170 found 6 days ago

St. Augustine economy flight packages

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.4/10 Very Good! (1,009 reviews)

May 18 - May 25

7 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
per person
The staff were absolutely wonderful. Always there when needed. Great experience! I will be returning 😊

Reviewed on Mar 2, 2024

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8/10 Very Good! (3,850 reviews)

May 21 - May 24

3 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
per person
Hotel was great! Friendly staff and nice amenities.

Reviewed on Mar 23, 2024

Westgate Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

7.4/10 Good! (1,043 reviews)

May 18 - May 25

7 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
The option of pools, and the water park. I wish the water park passes were included with your stay, the tickets are $25 a person each day.

Reviewed on Apr 3, 2024

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Prices and availability subject to change. Additional terms may apply.

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, Air Canada, JAL, Azul, Copa Airlines, Gol, Swiss, Air New Zealand, United Airlines, Alaska Airlines, Frontier Airlines, Cathay Pacific, Southwest Airlines, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, British Airways
Earliest Flight Arrival
1:42PM UTC
Latest Flight Arrival
2:43AM UTC

Chicago to St. Augustine

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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.