$23 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.

Sat, Feb 7 - Wed, Feb 11
ORD
O'Hare Intl.
MCO
Orlando Intl.
$141 Roundtrip, found 1 hour ago
$141
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Feb 7 from O'Hare Intl. to Orlando Intl., returning Wed, Feb 11, priced at $141 found 1 hour ago
Sun, Feb 8 - Tue, Feb 10
MDW
Midway Intl.
MCO
Orlando Intl.
$152 Roundtrip, found 13 hours ago
$152
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sun, Feb 8 from Midway Intl. to Orlando Intl., returning Tue, Feb 10, priced at $152 found 13 hours ago
Sat, Feb 7 - Sat, Feb 7
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Feb 7 from O'Hare Intl. to Jacksonville Intl., returning Sat, Feb 7, priced at $204 found 2 days ago
Sun, Feb 8 - Wed, Feb 11
RFD
Greater Rockford
MCO
Orlando Intl.
$323 Roundtrip, found 3 days ago
$323
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Feb 8 from Greater Rockford to Orlando Intl., returning Wed, Feb 11, priced at $323 found 3 days ago

Airfares from $23 One Way, $47 Round Trip from Chicago to St. Augustine

Prices starting at $47 for return flights and $23 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, Mar 3 - Sat, Mar 7
ORD
Chicago
MCO
Orlando
$47 Roundtrip, just found
$47
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Mar 3 from Chicago to Orlando, returning Sat, Mar 7, priced at $47 just found
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
MCO
Orlando
$66 Roundtrip, found 3 hours ago
$66
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Mar 3 from Chicago to Orlando, returning Tue, Mar 10, priced at $66 found 3 hours ago
Tue, Mar 10 - Wed, Mar 11
MDW
Chicago
MCO
Orlando
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Mar 10 from Chicago to Orlando, returning Wed, Mar 11, priced at $85 found 1 day ago
Mon, Feb 23 - Thu, Feb 26
ORD
Chicago
JAX
Jacksonville
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Chicago to Jacksonville, returning Thu, Feb 26, priced at $149 found 1 day ago
Sat, Mar 7 - Wed, Mar 11
RFD
Rockford
MCO
Orlando
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Mar 7 from Rockford to Orlando, returning Wed, Mar 11, priced at $159 found 6 days ago

St. Augustine economy flight packages

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

Westgate Vacation Villas Resort

8/10 Very Good! (1,703 reviews)

Mar 7 - Mar 10

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
Price was $377, price is now $189 per person
$189
per person
found 1 day ago
Always a good time at Westgate Resort

Reviewed on May 3, 2025

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.2/10 Very Good! (5,145 reviews)

Mar 5 - Mar 8

3 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Coach
Price was $778, price is now $249 per person
$249
per person
found 1 day ago
Simply not impressed- even for the price it was not very clean and high resort fee for no housekeeping daily. Requested towels and was given 2 for a family of 4

Reviewed on Jan 31, 2026

Westgate Towers Resort
3.5-star property

Westgate Towers Resort

8.6/10 Excellent! (1,002 reviews)

Mar 7 - Mar 11

4 night stay

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (ORD)

Spirit Airlines • Coach
Price was $449, price is now $219 per person
$219
per person
found 20 hours ago
Great place and very clean. They provide so many amenities

Reviewed on Aug 24, 2025

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St. Augustine first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Grove Resort & Water Park Orlando
4.0-star property

The Grove Resort & Water Park Orlando

8/10 Very Good! (8,735 reviews)

Mar 27 - Apr 2

6 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (ORD)

Delta • FirstClass
Price was $1,969, price is now $1,573 per person
$1,573
per person
found 1 day ago
The room was fantastic and we enjoyed the pool area. The woman who checked us in was not friendly though.

Reviewed on Jan 7, 2026

Evermore Orlando Resort
4.0-star property

Evermore Orlando Resort

9.6/10 Exceptional! (489 reviews)

Mar 27 - Apr 2

6 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (ORD)

Delta • FirstClass
Price was $5,086, price is now $3,545 per person
$3,545
per person
found 1 day ago
Amazing for families visting Orlando.

Reviewed on Oct 24, 2025

Meliá Orlando Celebration
4.0-star property

Meliá Orlando Celebration

8.6/10 Excellent! (1,549 reviews)

Mar 27 - Apr 2

6 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (ORD)

Delta • FirstClass
Price was $1,951, price is now $1,643 per person
$1,643
per person
found 1 day ago
Room was spacious and clean. It was like having your own apartment. A full-kitchen, separate shower and bath, and a balcony in the bedroom. Very friendly and helpful staff. The hotel had plenty of social activities for guests and is a short distance from Disney, downtown Celebration, and many restaurants. The balcony doors were hard to open and there was weed smell in some of the hallways.

Reviewed on Nov 12, 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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to St. Augustine

Great Deals on Flights From Chicago to St. Augustine

Spend more of your time and money at St. Augustine instead of sitting at your computer, searching for discount Chicago to St. Augustine flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to St. Augustine.

Flights That Fit Your Budget

Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to St. Augustine flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.

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Orbitz offers free mobile apps for iPad, iPhone, and Android-based devices, so even the busiest trip-planner can research and book flights from Chicago to St. Augustine. Find cheap Chicago to St. Augustine flights, research local festivities and attractions, and book reservations while sitting in the salon. Orbitz will also update you on flight delays with free alerts sent to your mobile phone or email address, so you’re never left in the dark.

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.

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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.