
$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.
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.
St. Augustine economy flight packages


Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
Aug 27 - Sep 1
Chicago (CHI) to Orlando (MCO)
Orlando (MCO) to Chicago (CHI)
Reviewed on Dec 23, 2023

Westgate Leisure Resort
Aug 20 - Aug 27
Chicago (ORD) to Orlando (MCO)
Reviewed on Mar 11, 2025
St. Augustine first class flight packages

Kompose Boutique Resort at Theme Parks
Aug 28 - Aug 31
Chicago (ORD) to Orlando (MCO)
Reviewed on Jul 11, 2025

Westgate Lakes Resort & Spa Universal Studios Area
Aug 28 - Aug 31
Chicago (ORD) to Orlando (MCO)
Reviewed on Jun 23, 2025

More About Flying To St. Augustine from Chicago
Route Information for Flights from Chicago to St. Augustine
Origin Airport IATA Code | CHI |
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Destination Airport IATA Code | JAX |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to St. Augustine
Orbitz is the best place to find guaranteed low prices on Chicago to St. Augustine flights. Because of our cutting-edge mobile tools and low fares on domestic and international flights, Orbitz is the best starting point for travelers.
Find Cheap Chicago to St. Augustine Flights
Orbitz offers free mobile apps for iPhone and Android devices—a great way to find fantastic deals on flights from Chicago to St. Augustine. Not only that, but you can check the status of your flight or even book low cost hotel rooms with the apps or on m.orbitz.com.
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Discount Travel Planning Made Simple
You will have no problems finding budget flights from Chicago to St. Augustine on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.
Flights to St. Augustine
- Miami 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.