$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, Jun 14 - Sat, Jun 21
MDW
Midway Intl.
MCO
Orlando Intl.
$262 Roundtrip, found 10 hours ago
$262
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Jun 14 from Midway Intl. to Orlando Intl., returning Sat, Jun 21, priced at $262 found 10 hours ago
Sun, Jun 15 - Wed, Jun 18
ORD
O'Hare Intl.
MCO
Orlando Intl.
$287 Roundtrip, just found
$287
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Jun 15 from O'Hare Intl. to Orlando Intl., returning Wed, Jun 18, priced at $287 just found
Sat, Jun 14 - Fri, Jul 4
MDW
Midway Intl.
JAX
Jacksonville Intl.
$555 Roundtrip, found 20 hours ago
$555
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Jun 14 from Midway Intl. to Jacksonville Intl., returning Fri, Jul 4, priced at $555 found 20 hours ago
Sun, Jun 15 - Sun, Jun 22
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$599 Roundtrip, found 7 hours ago
$599
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sun, Jun 15 from O'Hare Intl. to Jacksonville Intl., returning Sun, Jun 22, priced at $599 found 7 hours ago

Airfares from $44 One Way, $104 Round Trip from Chicago to St. Augustine

Prices starting at $104 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.

Tue, Jul 1 - Wed, Jul 2
ORD
Chicago
MCO
Orlando
$104 Roundtrip, found 15 hours ago
$104
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Tue, Jul 1 from Chicago to Orlando, returning Wed, Jul 2, priced at $104 found 15 hours ago
Sun, Jun 29 - Wed, Jul 2
ORD
Chicago
MCO
Orlando
$108 Roundtrip, found 4 hours ago
$108
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sun, Jun 29 from Chicago to Orlando, returning Wed, Jul 2, priced at $108 found 4 hours ago
Mon, Sep 22 - Sat, Sep 27
MDW
Chicago
MCO
Orlando
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Sep 22 from Chicago to Orlando, returning Sat, Sep 27, priced at $138 found 6 days ago
Fri, Sep 12 - Sun, Sep 14
MDW
Chicago
JAX
Jacksonville
$154 Roundtrip, found 3 days ago
$154
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Chicago to Jacksonville, returning Sun, Sep 14, priced at $154 found 3 days ago
Fri, Sep 12 - Sun, Sep 14
ORD
Chicago
JAX
Jacksonville
$154 Roundtrip, found 3 days ago
$154
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Chicago to Jacksonville, returning Sun, Sep 14, priced at $154 found 3 days 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! (1,262 reviews)

Jul 24 - Jul 27

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
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

8.6/10 Excellent! (1,000 reviews)

Jul 20 - Jul 23

3 night stay

Chicago (CHI) to Orlando (MCO)

United • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
per person
found 1 day ago
I am gonna stay again in December when I go back to Orlando this is the most best place I ever stayed when I visit Florida

Reviewed on Apr 24, 2025

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

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (4,996 reviews)

Jul 24 - Jul 27

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
It felt high quality like a Disney resort

Reviewed on May 13, 2025

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St. Augustine first class 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! (1,262 reviews)

Aug 2 - Aug 7

5 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop • FirstClass

Orlando (MCO) to Chicago (ORD)

United • Non-stop • FirstClass
per person
found 15 hours 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

8.6/10 Excellent! (1,000 reviews)

Aug 2 - Aug 7

5 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop • FirstClass

Orlando (MCO) to Chicago (ORD)

United • Non-stop • FirstClass
Save 100% on your flight
per person
found 15 hours ago
I am gonna stay again in December when I go back to Orlando this is the most best place I ever stayed when I visit Florida

Reviewed on Apr 24, 2025

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

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (4,996 reviews)

Aug 2 - Aug 7

5 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop • FirstClass

Orlando (MCO) to Chicago (ORD)

United • Non-stop • FirstClass
per person
found 15 hours ago
It felt high quality like a Disney resort

Reviewed on May 13, 2025

Don't see what you're looking for?
See all available trips from Chicago to St. Augustine
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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, 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, British Airways
Earliest Flight Arrival
12:58PM UTC
Latest Flight Arrival
2:27AM UTC

Chicago to St. Augustine

Looking for cheap Chicago to St. Augustine flights? Orbitz has the cheapest air fares for flights from Chicago to St. Augustine. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.

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Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Chicago to St. Augustine flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Chicago to St. Augustine on your mobile device too, including delays and baggage claim details.

Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Chicago to St. Augustine flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to St. Augustine. Need hotels too? You can book them last minute on your mobile phone.

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.