$24 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, Mar 2 - Wed, Mar 12
ORD
O'Hare Intl.
MCO
Orlando Intl.
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Mar 2 from O'Hare Intl. to Orlando Intl., returning Wed, Mar 12, priced at $127 just found
Sat, Mar 1 - Tue, Mar 4
MDW
Midway Intl.
MCO
Orlando Intl.
$174 Roundtrip, just found
$174
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Mar 1 from Midway Intl. to Orlando Intl., returning Tue, Mar 4, priced at $174 just found
Sun, Mar 2 - Tue, Mar 11
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$402 Roundtrip, found 7 hours ago
$402
Roundtrip
found 7 hours ago
Select Delta flight, departing Sun, Mar 2 from O'Hare Intl. to Jacksonville Intl., returning Tue, Mar 11, priced at $402 found 7 hours ago
Sat, Mar 1 - Sat, Mar 8
ORD
O'Hare Intl.
DAB
Daytona Beach Intl.
$462 Roundtrip, found 8 hours ago
$462
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Mar 1 from O'Hare Intl. to Daytona Beach Intl., returning Sat, Mar 8, priced at $462 found 8 hours ago

Airfares from $24 One Way, $74 Round Trip from Chicago to St. Augustine

Prices starting at $74 for return flights and $24 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.

Sat, Mar 1 - Wed, Mar 19
ORD
Chicago
MCO
Orlando
$74 Roundtrip, found 2 days ago
$74
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Mar 1 from Chicago to Orlando, returning Wed, Mar 19, priced at $74 found 2 days ago
Wed, May 7 - Tue, May 13
ORD
Chicago
MCO
Orlando
$85 Roundtrip, found 6 hours ago
$85
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, May 7 from Chicago to Orlando, returning Tue, May 13, priced at $85 found 6 hours ago
Thu, Mar 27 - Tue, Apr 1
MDW
Chicago
JAX
Jacksonville
$173 Roundtrip, found 2 days ago
$173
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Mar 27 from Chicago to Jacksonville, returning Tue, Apr 1, priced at $173 found 2 days ago
Mon, Apr 14 - Thu, May 1
ORD
Chicago
JAX
Jacksonville
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Apr 14 from Chicago to Jacksonville, returning Thu, May 1, priced at $185 found 3 days ago
Tue, May 13 - Wed, May 21
ORD
Chicago
MCO
Orlando
$190 Roundtrip, found 6 hours ago
$190
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, May 13 from Chicago to Orlando, returning Wed, May 21, priced at $190 found 6 hours ago

St. Augustine economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
3.5-star property

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

8.6/10 Excellent! (490 reviews)

Apr 13 - Apr 18

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
per person
found 6 hours ago
This is the place to stay if you want a real feel for the warmth & charm of St.Augustine & its people instead of a cold impersonal hotel. The staff provided wonderful support in every need of our visit. Their breakfast & coffee are excellent and will accommodate any request if possible. We stayed 1night for the Christmas Nights of Lights and I can safely say that we will be back. The plus side, the beach is a five walk from the hotel. At Checkout, Selim was so gracious and lovely. We will be back in the summer for sure.

Reviewed on Dec 23, 2023

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8/10 Very Good! (4,903 reviews)

Apr 11 - Apr 19

8 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
The mattress was so much smaller than the bed frame. Awkward to get on and off with out scrapping your legs.

Reviewed on Feb 15, 2025

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

Westgate Palace Hotel / Universal / I-Drive

8.4/10 Very Good! (1,006 reviews)

Apr 11 - Apr 19

8 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
Very quiet, convenient to everything

Reviewed on Jan 2, 2025

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St. Augustine first class flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

7.8/10 Good! (1,149 reviews)

Apr 11 - Apr 17

6 night stay

Chicago (ORD) to Orlando (MCO)

United • Roundtrip • FirstClass
per person
found 1 day ago
Poor signage and diffucult to find check in. Long wait for check in at 1am.

Reviewed on Feb 15, 2025

Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8/10 Very Good! (4,141 reviews)

Apr 11 - Apr 17

6 night stay

Chicago (ORD) to Orlando (MCO)

United • Roundtrip • FirstClass
per person
found 1 day ago
The staff was very friendly. We had a very early flight that got us to the resort hours before our check in time. Jessica the girls at the desk put us in a room in a very quiet area of the resort, 4 hours before the regular check in. The pool and area was very clean. The food and drink at the pool bars was very reasonable. Actually cheaper then most places off the property. My wife and I stayed 4 days and had a blast. Can’t beat this property at this price point. Thank you WG staff. Phil Gormley.

Reviewed on Feb 17, 2025

ette hotel
5.0-star property

ette hotel

9.8/10 Exceptional! (249 reviews)

Apr 11 - Apr 17

6 night stay

Chicago (ORD) to Orlando (MCO)

United • Roundtrip • FirstClass
per person
found 1 day ago
Beautiful and very clean place to stay. We definitely will be back.

Reviewed on Sep 23, 2023

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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

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.