$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 1 hour ago
$189
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Nov 29 from Midway Intl. to Orlando Intl., returning Fri, Dec 6, priced at $189 found 1 hour ago
Sat, Nov 30 - Tue, Dec 3
ORD
O'Hare Intl.
MCO
Orlando Intl.
$305 Roundtrip, just found
$305
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Nov 30 from O'Hare Intl. to Orlando Intl., returning Tue, Dec 3, priced at $305 just found
Sat, Nov 30 - Fri, Dec 6
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$462 Roundtrip, found 16 hours ago
$462
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sat, Nov 30 from O'Hare Intl. to Jacksonville Intl., returning Fri, Dec 6, priced at $462 found 16 hours 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 1 hour ago
$77
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Mon, Dec 9 from Chicago to Orlando, returning Tue, Dec 17, priced at $77 found 1 hour ago
Mon, Feb 3 - Thu, Feb 6
MDW
Chicago
MCO
Orlando
$118 Roundtrip, found 13 hours ago
$118
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, Feb 3 from Chicago to Orlando, returning Thu, Feb 6, priced at $118 found 13 hours 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
Tue, Jan 7 - Sat, Jan 11
ORD
Chicago
MCO
Orlando
$157 Roundtrip, just found
$157
Roundtrip
just found
Select United flight, departing Tue, Jan 7 from Chicago to Orlando, returning Sat, Jan 11, priced at $157 just found
Tue, Feb 11 - Sat, Feb 15
ORD
Chicago
MCO
Orlando
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Feb 11 from Chicago to Orlando, returning Sat, Feb 15, priced at $157 found 1 hour ago

St. Augustine economy flight packages

Price found within the past 48 hours. Click for updated prices.
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

Parkway International Resort
3.0-star property

Parkway International Resort

9.4/10 Exceptional! (1,650 reviews)

Dec 26 - Dec 31

5 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 5 hours ago
Awesome place will definitely be staying here again.

Reviewed on Jul 29, 2024

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

7.8/10 Good! (1,163 reviews)

Jan 16 - Jan 21

5 night stay

Chicago (MDW) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
El aire acondicionado no funciona bien , todo el tiempo a 75 y no baja, llamamos y fueron el último día antes de irnos, todo lo demás excelente

Reviewed on May 28, 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
1006 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Azul, Emirates, Copa Airlines, Gol, Air New Zealand, Swiss, United Airlines, Alaska Airlines, Frontier Airlines, Cathay Pacific, Southwest Airlines, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Spirit Airlines
Earliest Flight Arrival
4:17PM 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.