$44 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 $44 One Way, $69 Round Trip from St. Augustine to Chicago

Prices starting at $69 for return flights and $44 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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Level Chicago - River North
Park Hyatt Chicago
Trump International Hotel & Tower Chicago
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Chicago first class flight packages

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JW Marriott Chicago
Trump International Hotel & Tower Chicago
Park Hyatt 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
1006 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Emirates, Copa Airlines, Swiss, Air New Zealand, United Airlines, Alaska Airlines, Cathay Pacific, Southwest Airlines, Royal Jordanian, ITA Airways, Iberia, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, British Airways
Earliest Flight Arrival
9:10PM UTC
Latest Flight Arrival
1:58AM UTC

St. Augustine to Chicago

For the best travel experience from St. Augustine to Chicago domestic and international travelers everywhere choose Orbitz for guaranteed low prices and cutting-edge mobile tools.

Convenient Low-Cost Travel

Orbitz makes it simple to book discount flights from St. Augustine to {destination.name} without compromising your schedule. You can always find deals on domestic flights from a location near you. You may find the best deals to fit your schedule by mixing and matching airlines to get you from St. Augustine to Chicago.

Access Orbitz On The Move

You can access Orbitz anywhere at anytime for travel from St. Augustine to Chicago using the latest technology. Via your mobile phone you can track any changes to your flight status, gate and baggage claim details, and with Orbitz’s full-service mobile apps for iPhone and Android you can view these trip details anytime anywhere. You can also get fare alerts and travel updates to keep you informed of the cheapest flights from St. Augustine to Chicago.

Earn Rewards on Your St. Augustine to Chicago Flights

At Orbitz you can benefit from low cost travel and have your loyalty rewarded on certain types of St. Augustine to Chicago flights. All you need to do is enter you frequent flyer number when booking and rack up your rewards through Orbitz online on the Traveler Information page for use on future flights. You can even add your frequent flyer number to an existing reservation to start the ball rolling.

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.