$53 Cheap flight deals from St. Augustine (JAX) to Chicago (CHI)

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This Weekend's Flight Deals from St. Augustine to Chicago

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 $53 One Way, $94 Round Trip from St. Augustine to Chicago

Prices starting at $94 for return flights and $53 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chicago economy flight packages

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The Wade
Level Chicago Fulton Market
Park Hyatt Chicago
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Chicago first class flight packages

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Hilton Chicago
Park Hyatt Chicago
Hotel Riu Plaza Chicago
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More About Flying To Chicago from St. Augustine

Route Information for Flights from St. Augustine to Chicago

Origin Airport IATA Code
JAX
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

St. Augustine to Chicago

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Take advantage of low fares on St. Augustine to Chicago flights and vacation packages

Orbitz has the best prices available on flights from St. Augustine to Chicago. Take advantage of our low fare sales and discounts and begin to plan your next trip. We also give you great savings on hotels, car rentals, and vacation packages.

Frequently asked questions

Are there non-stop flights from St. Augustine to Chicago?
Yes, you'll find direct flights from Orlando Intl. Airport (MCO) to O'Hare Airport. What's more, there are 5 airlines for you to select from. Pretty cool, huh? Check which of these sought-after carriers meets your needs:

  • United Airlines
  • American Airlines
  • Spirit Airlines
  • Southwest Airlines
  • Frontier Airlines

What is the shortest flight from St. Augustine to Chicago?
If conditions are good and everything goes to plan, you could be flying into MDW from JAX in just 2 hours and 50 minutes. With such a brief flight time, contemplate taking just hand luggage.
What airlines fly from St. Augustine to Chicago most frequently?
We all have our preferences when it comes to airlines, and you have a good variety when traveling from St. Augustine to Chicago. These top four carriers service this route the most: 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.