$39 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.

Fri, Nov 29 - Fri, Dec 6
MDW
Midway Intl.
MCO
Orlando Intl.
$189 Roundtrip, found 5 hours ago
$189
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Nov 29 from Midway Intl. to Orlando Intl., returning Fri, Dec 6, priced at $189 found 5 hours ago
Fri, Nov 29 - Wed, Dec 4
ORD
O'Hare Intl.
MCO
Orlando Intl.
$207 Roundtrip, just found
$207
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 29 from O'Hare Intl. to Orlando Intl., returning Wed, Dec 4, priced at $207 just found
Fri, Nov 29 - Fri, Dec 6
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$454 Roundtrip, found 1 hour ago
$454
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Nov 29 from O'Hare Intl. to Jacksonville Intl., returning Fri, Dec 6, priced at $454 found 1 hour ago
Fri, Nov 29 - Wed, Dec 11
ORD
O'Hare Intl.
DAB
Daytona Beach Intl.
$466 Roundtrip, found 3 days ago
$466
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Nov 29 from O'Hare Intl. to Daytona Beach Intl., returning Wed, Dec 11, priced at $466 found 3 days ago

Airfares from $39 One Way, $77 Round Trip from Chicago to St. Augustine

Prices starting at $77 for return flights and $39 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.

Mon, Dec 9 - Tue, Dec 17
ORD
Chicago
MCO
Orlando
$77 Roundtrip, found 2 hours ago
$77
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Mon, Dec 9 from Chicago to Orlando, returning Tue, Dec 17, priced at $77 found 2 hours ago
Mon, Dec 16 - Tue, Dec 17
MDW
Chicago
MCO
Orlando
$107 Roundtrip, found 2 hours ago
$107
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Dec 16 from Chicago to Orlando, returning Tue, Dec 17, priced at $107 found 2 hours ago
Tue, Dec 17 - Thu, Dec 19
ORD
Chicago
MCO
Orlando
$107 Roundtrip, found 1 hour ago
$107
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Dec 17 from Chicago to Orlando, returning Thu, Dec 19, priced at $107 found 1 hour ago
Tue, Dec 17 - Mon, Jan 6
MDW
Chicago
JAX
Jacksonville
$138 Roundtrip, found 4 days ago
$138
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Dec 17 from Chicago to Jacksonville, returning Mon, Jan 6, priced at $138 found 4 days ago
Sat, Jan 18 - Tue, Jan 21
ORD
Chicago
MCO
Orlando
$157 Roundtrip, just found
$157
Roundtrip
just found
Select United flight, departing Sat, Jan 18 from Chicago to Orlando, returning Tue, Jan 21, priced at $157 just found

St. Augustine economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

7.8/10 Good! (3,850 reviews)

Jan 10 - Jan 14

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Westgate is where you feel like you are at home. I didn't want to leave. I would definitely bring my family back. I am not able to do a lot of walking so, the room was in a perfect place. First floor near the door. I could also see my car if I looked out the window.

Reviewed on Oct 29, 2024

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8/10 Very Good! (4,697 reviews)

Jan 10 - Jan 14

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
per person
found 1 day ago
Really nice staff and good service

Reviewed on Nov 6, 2024

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

Westgate Palace Hotel / Universal / I-Drive

8.4/10 Very Good! (1,005 reviews)

Jan 10 - Jan 14

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
per person
found 1 day ago
Pool hours opened late my kid loved it

Reviewed on Jul 23, 2024

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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.