$44 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, Sep 20 - Mon, Sep 22
MDW
Midway Intl.
MCO
Orlando Intl.
$115 Roundtrip, found 12 hours ago
$115
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, Sep 20 from Midway Intl. to Orlando Intl., returning Mon, Sep 22, priced at $115 found 12 hours ago
Sun, Sep 21 - Thu, Sep 25
ORD
O'Hare Intl.
MCO
Orlando Intl.
$176 Roundtrip, found 1 hour ago
$176
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, Sep 21 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 25, priced at $176 found 1 hour ago
Sun, Sep 21 - Mon, Sep 29
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$243 Roundtrip, found 15 hours ago
$243
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sun, Sep 21 from O'Hare Intl. to Jacksonville Intl., returning Mon, Sep 29, priced at $243 found 15 hours ago
Fri, Sep 19 - Sun, Sep 21
MDW
Midway Intl.
JAX
Jacksonville Intl.
$476 Roundtrip, found 19 hours ago
$476
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Fri, Sep 19 from Midway Intl. to Jacksonville Intl., returning Sun, Sep 21, priced at $476 found 19 hours ago

Airfares from $44 One Way, $87 Round Trip from Chicago to St. Augustine

Prices starting at $87 for return flights and $44 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, Oct 4 - Tue, Oct 7
ORD
Chicago
MCO
Orlando
$87 Roundtrip, found 1 hour ago
$87
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Oct 4 from Chicago to Orlando, returning Tue, Oct 7, priced at $87 found 1 hour ago
Thu, Dec 4 - Mon, Dec 8
MDW
Chicago
MCO
Orlando
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Chicago to Orlando, returning Mon, Dec 8, priced at $92 found 1 day ago
Tue, Dec 2 - Tue, Dec 9
ORD
Chicago
MCO
Orlando
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Dec 2 from Chicago to Orlando, returning Tue, Dec 9, priced at $133 found 1 day ago
Tue, Dec 2 - Tue, Dec 9
ORD
Chicago
MCO
Orlando
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 2 from Chicago to Orlando, returning Tue, Dec 9, priced at $133 found 1 day ago
Sat, Oct 11 - Sat, Oct 18
ORD
Chicago
JAX
Jacksonville
$135 Roundtrip, found 1 day ago
$135
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 11 from Chicago to Jacksonville, returning Sat, Oct 18, priced at $135 found 1 day 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

8/10 Very Good! (1,361 reviews)

Oct 30 - Nov 3

4 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $505, price is now $270 per person
$270
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

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

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,007 reviews)

Oct 30 - Nov 3

4 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Price was $796, price is now $372 per person
$372
per person
found 1 day ago
The location is conveniently close to Universal, with a nearby 7-Eleven and several restaurants. The room is clean and pleasant, and parking is easily accessible.

Reviewed on Aug 6, 2025

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

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,303 reviews)

Nov 6 - Nov 11

5 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $703, price is now $344 per person
$344
per person
found 1 day ago
Overall it was a good stay. I would recommend this place especially for the price. I like that they had shuttle service to and from parks. The only negative was that the only way to cut through to my room from lobby was through the pool area. If the pool area was closed due to storms could not go through and needed to walk all the way around. Hotel should add path or leave pool area open with a few closed signs on gates to let people know pool was closed for swimming, but would still allow people to pass through.

Reviewed on Aug 22, 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

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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.