$46 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 6 - Tue, Apr 8
MDW
Midway Intl.
MCO
Orlando Intl.
$139 Roundtrip, found 3 hours ago
$139
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Apr 6 from Midway Intl. to Orlando Intl., returning Tue, Apr 8, priced at $139 found 3 hours ago
Sat, Apr 5 - Tue, Apr 8
ORD
O'Hare Intl.
MCO
Orlando Intl.
$169 Roundtrip, just found
$169
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Apr 5 from O'Hare Intl. to Orlando Intl., returning Tue, Apr 8, priced at $169 just found
Sun, Apr 6 - Tue, Apr 8
MDW
Midway Intl.
JAX
Jacksonville Intl.
$248 Roundtrip, found 2 days ago
$248
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Apr 6 from Midway Intl. to Jacksonville Intl., returning Tue, Apr 8, priced at $248 found 2 days ago
Sat, Apr 5 - Thu, Apr 24
ORD
O'Hare Intl.
DAB
Daytona Beach Intl.
$516 Roundtrip, found 1 day ago
$516
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Apr 5 from O'Hare Intl. to Daytona Beach Intl., returning Thu, Apr 24, priced at $516 found 1 day ago

Airfares from $46 One Way, $92 Round Trip from Chicago to St. Augustine

Prices starting at $92 for return flights and $46 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, Apr 8 - Thu, Apr 10
ORD
Chicago
MCO
Orlando
$92 Roundtrip, just found
$92
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Apr 8 from Chicago to Orlando, returning Thu, Apr 10, priced at $92 just found
Sat, May 10 - Wed, May 14
MDW
Chicago
MCO
Orlando
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, May 10 from Chicago to Orlando, returning Wed, May 14, priced at $177 found 1 day ago
Sat, May 3 - Tue, May 6
ORD
Chicago
JAX
Jacksonville
$203 Roundtrip, found 11 hours ago
$203
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Sat, May 3 from Chicago to Jacksonville, returning Tue, May 6, priced at $203 found 11 hours ago
Fri, Apr 25 - Fri, May 2
MDW
Chicago
JAX
Jacksonville
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Apr 25 from Chicago to Jacksonville, returning Fri, May 2, priced at $210 found 2 days ago
Fri, Jun 6 - Tue, Jun 10
ORD
Chicago
DAB
Daytona Beach
$316 Roundtrip, found 2 hours ago
$316
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Jun 6 from Chicago to Daytona Beach, returning Tue, Jun 10, priced at $316 found 2 hours ago

St. Augustine economy 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! (1,199 reviews)

May 1 - May 5

4 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
found 1 day ago
Poor signage and diffucult to find check in. Long wait for check in at 1am.

Reviewed on Feb 15, 2025

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! (508 reviews)

May 15 - May 20

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Non-stop • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
per person
found 1 day 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

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

Westgate Lakes Resort & Spa Universal Studios Area

8/10 Very Good! (4,595 reviews)

May 1 - May 5

4 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
found 1 day ago
Place is amazing. I Always stay there. Parking is the only thing they need to work on, they need to assign at least one space per unit. They do have a parking deck and parking is first come first serve in the whole area so you will have some where to park, but be nice to park infront of your unit.

Reviewed on Feb 23, 2025

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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
1006 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Air Canada, JAL, Azul, Copa Airlines, Swiss, Air New Zealand, United Airlines, Gol, Alaska Airlines, Frontier Airlines, Cathay Pacific, Royal Jordanian, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, British Airways
Earliest Flight Arrival
2:31PM UTC
Latest Flight Arrival
4:59AM 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.