$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, Jul 19 - Tue, Jul 22
MDW
Midway Intl.
MCO
Orlando Intl.
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 19 from Midway Intl. to Orlando Intl., returning Tue, Jul 22, priced at $164 found 3 days ago
Fri, Jul 18 - Sun, Jul 27
ORD
O'Hare Intl.
MCO
Orlando Intl.
$255 Roundtrip, just found
$255
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jul 18 from O'Hare Intl. to Orlando Intl., returning Sun, Jul 27, priced at $255 just found
Fri, Jul 18 - Mon, Jul 21
MDW
Midway Intl.
JAX
Jacksonville Intl.
$271 Roundtrip, found 4 days ago
$271
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Jul 18 from Midway Intl. to Jacksonville Intl., returning Mon, Jul 21, priced at $271 found 4 days ago
Fri, Jul 18 - Sun, Jul 20
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$371 Roundtrip, found 16 hours ago
$371
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Fri, Jul 18 from O'Hare Intl. to Jacksonville Intl., returning Sun, Jul 20, priced at $371 found 16 hours ago

Airfares from $44 One Way, $97 Round Trip from Chicago to St. Augustine

Prices starting at $97 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.

Wed, Aug 6 - Fri, Aug 8
ORD
Chicago
MCO
Orlando
$97 Roundtrip, found 1 hour ago
$97
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Aug 6 from Chicago to Orlando, returning Fri, Aug 8, priced at $97 found 1 hour ago
Tue, Sep 16 - Sat, Sep 20
MDW
Chicago
JAX
Jacksonville
$105 Roundtrip, found 6 days ago
$105
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Jacksonville, returning Sat, Sep 20, priced at $105 found 6 days ago
Sat, Sep 20 - Tue, Sep 30
ORD
Chicago
JAX
Jacksonville
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 20 from Chicago to Jacksonville, returning Tue, Sep 30, priced at $105 found 4 days ago
Sat, Sep 20 - Tue, Sep 30
ORD
Chicago
JAX
Jacksonville
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select United flight, departing Sat, Sep 20 from Chicago to Jacksonville, returning Tue, Sep 30, priced at $105 found 4 days ago
Fri, Sep 5 - Mon, Sep 8
MDW
Chicago
MCO
Orlando
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Chicago to Orlando, returning Mon, Sep 8, priced at $119 found 3 days ago

St. Augustine economy flight packages

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites
2.5-star property

Boardwalk Inn and Suites

8.4/10 Very Good! (1,341 reviews)

Aug 22 - Aug 25

3 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Nice ocean view and sun rise

Reviewed on Jan 26, 2025

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
3.5-star property

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

8.6/10 Excellent! (543 reviews)

Aug 27 - Sep 1

5 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Chicago (CHI)

United • Coach
Save 100% on your flight
per person
found 1 day ago
This is the place to stay if you want a real feel for the warmth & charm of St.Augustine & its people instead of a cold impersonal hotel. The staff provided wonderful support in every need of our visit. Their breakfast & coffee are excellent and will accommodate any request if possible. We stayed 1night for the Christmas Nights of Lights and I can safely say that we will be back. The plus side, the beach is a five walk from the hotel. At Checkout, Selim was so gracious and lovely. We will be back in the summer for sure.

Reviewed on Dec 23, 2023

Westgate Leisure Resort
3.5-star property

Westgate Leisure Resort

8.4/10 Very Good! (911 reviews)

Aug 20 - Aug 27

7 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This property fit what we wanted for our trip - a condo with a kitchen, two bedrooms, two bathrooms, and affordable. The rooms need updating and more attention to cleaning, but otherwise, it is a nice property.

Reviewed on Mar 11, 2025

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St. Augustine first class flight packages

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Resort at Theme Parks
4.0-star property

Kompose Boutique Resort at Theme Parks

9.6/10 Exceptional! (554 reviews)

Aug 28 - Aug 31

3 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • Roundtrip • FirstClass
per person
found 1 day ago
The staff offered outstanding customer service. Property was beautiful, granted it is brand new. The rooms were like an apartment suite. It was really nice having a washer/dryer in the unit. Property was extremely clean. This is definitely a property that i would consider staying at again. Pool was nice. Offering warer slides kept children at the far end of the pool. Property was much closer to Disney parks.

Reviewed on Jul 11, 2025

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

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,097 reviews)

Aug 28 - Aug 31

3 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • Roundtrip • FirstClass
per person
found 1 day ago
Pros: Clean, beautiful grounds. There are pools throughout the property, and food/store options available onsite. Beds were comfortable. Nice patios. Able to get bus to Universal for free. Cons: Check in was awful. Took close to 1 hour. There is a shuttle that can take you from your building to the front as it's a long walk. However, we mostly had to walk because the shuttle was either parked up front or MIA. The property and rooms are dated. Plugs/outlets in the room were few and we had two just not even work in our room. The waterpark was fine, but requires additional paid entry for non-members. Pools on property are just open swimming..no attendants.

Reviewed on Jun 23, 2025

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,000 reviews)

Aug 28 - Aug 31

3 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • Roundtrip • FirstClass
per person
found 1 day ago
Great location for hospital access

Reviewed on Jul 8, 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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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.