$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.

Sun, Feb 22 - Wed, Feb 25
ORD
O'Hare Intl.
MCO
Orlando Intl.
$202 Roundtrip, found 2 hours ago
$202
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Feb 22 from O'Hare Intl. to Orlando Intl., returning Wed, Feb 25, priced at $202 found 2 hours ago
Sat, Feb 21 - Fri, Feb 27
MDW
Midway Intl.
MCO
Orlando Intl.
$230 Roundtrip, found 2 hours ago
$230
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Midway Intl. to Orlando Intl., returning Fri, Feb 27, priced at $230 found 2 hours ago
Fri, Feb 20 - Sun, Feb 22
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$347 Roundtrip, found 17 hours ago
$347
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Feb 20 from O'Hare Intl. to Jacksonville Intl., returning Sun, Feb 22, priced at $347 found 17 hours ago
Fri, Feb 20 - Fri, Feb 27
ORD
O'Hare Intl.
DAB
Daytona Beach Intl.
$465 Roundtrip, found 5 days ago
$465
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Feb 20 from O'Hare Intl. to Daytona Beach Intl., returning Fri, Feb 27, priced at $465 found 5 days ago

Airfares from $44 One Way, $68 Round Trip from Chicago to St. Augustine

Prices starting at $68 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.

Mon, Apr 20 - Sat, Apr 25
MDW
Chicago
MCO
Orlando
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Apr 20 from Chicago to Orlando, returning Sat, Apr 25, priced at $68 found 1 day ago
Tue, Mar 10 - Wed, Mar 11
ORD
Chicago
MCO
Orlando
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Mar 10 from Chicago to Orlando, returning Wed, Mar 11, priced at $73 found 1 day ago
Sat, Apr 11 - Sat, Apr 18
ORD
Chicago
JAX
Jacksonville
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select United flight, departing Sat, Apr 11 from Chicago to Jacksonville, returning Sat, Apr 18, priced at $138 found 2 days ago
Sat, Apr 25 - Tue, Apr 28
RFD
Rockford
MCO
Orlando
$157 Roundtrip, found 23 hours ago
$157
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Sat, Apr 25 from Rockford to Orlando, returning Tue, Apr 28, priced at $157 found 23 hours ago
Thu, May 14 - Sun, May 17
MDW
Chicago
JAX
Jacksonville
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 14 from Chicago to Jacksonville, returning Sun, May 17, priced at $160 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! (1,367 reviews)

Mar 21 - Mar 24

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $587, price is now $337 per person
$337
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 Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

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

Apr 3 - Apr 7

4 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $705, price is now $377 per person
$377
per person
found 1 day ago
Nice pools and Hot tubs. Room I had needed some updating but was a nice lay out. Could see Disney fireworks from slider!

Reviewed on Feb 16, 2026

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

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,482 reviews)

Mar 20 - Mar 24

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
Price was $881, price is now $497 per person
$497
per person
found 1 day ago
We had to get 4 room keys for our door to finally work, however staff was kind and helped us as much as they could.

Reviewed on Feb 12, 2026

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St. Augustine packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Westgate Blue Tree Resort in Lake Buena Vista
3.5-star property

Westgate Blue Tree Resort in Lake Buena Vista

8.4/10 Very Good! (1,002 reviews)

Mar 27 - Mar 30

3 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (CHI)

Delta • PremiumEconomy
Price was $845, price is now $645 per person
$645
per person
found 1 day ago
The place is very nice! However, the washer did not work.

Reviewed on Oct 31, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays
4.0-star property

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9.2/10 Wonderful! (1,001 reviews)

Mar 27 - Mar 30

3 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (CHI)

Delta • PremiumEconomy
Price was $1,325, price is now $1,046 per person
$1,046
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

Parkway International Resort
3.0-star property

Parkway International Resort

9.6/10 Exceptional! (2,052 reviews)

Mar 27 - Mar 30

3 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (CHI)

Delta • PremiumEconomy
Price was $810, price is now $674 per person
$674
per person
found 1 day ago
The list is endless... we were not expecting what we were looking at wgen we opened the door. This is now are go to place to stay when we're in Florida.

Reviewed on Nov 17, 2025

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St. Augustine first class flight packages

Price found within the past 48 hours. Click for updated prices.
St George Inn
3.5-star property

St George Inn

9.6/10 Exceptional! (998 reviews)

Mar 28 - Apr 1

4 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • Roundtrip • FirstClass
Price was $2,081, price is now $1,821 per person
$1,821
per person
found 22 hours ago
Right at the north end of the historic district, great location, very helpful staff, very charming. Parking and getting in/out are tough due to the popular location though.

Reviewed on Apr 7, 2024

Hampton Inn Jacksonville Beach/Oceanfront
3.0-star property

Hampton Inn Jacksonville Beach/Oceanfront

9.2/10 Wonderful! (2,552 reviews)

Mar 28 - Apr 1

4 night stay

Chicago (ORD) to Jacksonville (JAX)

United • Roundtrip • FirstClass
Price was $2,255, price is now $2,073 per person
$2,073
per person
found 20 hours ago
Great location, friendly staff, very comfortable. The hotel has everything you need. Beautiful pool and a hot tub are a great bonus!

Reviewed on Feb 16, 2026

The Kenwood Inn
3.5-star property

The Kenwood Inn

9.6/10 Exceptional! (321 reviews)

Mar 28 - Apr 1

4 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • Roundtrip • FirstClass
Price was $2,116, price is now $1,823 per person
$1,823
per person
found 22 hours ago
Staff was great. Breakfast was great. Guests were nice and respectful. My only complaint was the bed in room 9 was not very good, it felt lopsided

Reviewed on Dec 16, 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.

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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.