$24 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.

Sat, Mar 14 - Wed, Mar 18
MCO
Orlando Intl.
MDW
Midway Intl.
$254 Roundtrip, found 8 hours ago
$254
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Mar 14 from Orlando Intl. to Midway Intl., returning Wed, Mar 18, priced at $254 found 8 hours ago
Fri, Mar 13 - Mon, Mar 16
MCO
Orlando Intl.
ORD
O'Hare Intl.
$280 Roundtrip, just found
$280
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Mar 13 from Orlando Intl. to O'Hare Intl., returning Mon, Mar 16, priced at $280 just found
Sun, Mar 15 - Thu, Mar 19
JAX
Jacksonville Intl.
MDW
Midway Intl.
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Mar 15 from Jacksonville Intl. to Midway Intl., returning Thu, Mar 19, priced at $300 found 1 day ago
Sun, Mar 15 - Thu, Mar 19
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$340 Roundtrip, found 1 day ago
$340
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Mar 15 from Jacksonville Intl. to O'Hare Intl., returning Thu, Mar 19, priced at $340 found 1 day ago

Airfares from $24 One Way, $68 Round Trip from St. Augustine to Chicago

Prices starting at $68 for return flights and $24 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.

Sat, May 9 - Mon, May 11
MCO
Orlando
ORD
Chicago
$68 Roundtrip, found 5 days ago
$68
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 9 from Orlando to Chicago, returning Mon, May 11, priced at $68 found 5 days ago
Thu, Apr 23 - Mon, Apr 27
MCO
Orlando
MDW
Chicago
$68 Roundtrip, found 5 days ago
$68
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Orlando to Chicago, returning Mon, Apr 27, priced at $68 found 5 days ago
Wed, Mar 11 - Tue, Apr 7
MCO
Orlando
ORD
Chicago
$97 Roundtrip, found 6 days ago
$97
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Mar 11 from Orlando to Chicago, returning Tue, Apr 7, priced at $97 found 6 days ago
Tue, May 5 - Sat, May 16
MCO
Orlando
ORD
Chicago
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, May 5 from Orlando to Chicago, returning Sat, May 16, priced at $157 found 6 days ago
Thu, Apr 23 - Sun, Apr 26
JAX
Jacksonville
MDW
Chicago
$160 Roundtrip, found 5 hours ago
$160
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Jacksonville to Chicago, returning Sun, Apr 26, priced at $160 found 5 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (3,438 reviews)

Apr 17 - Apr 20

3 night stay

Jacksonville (JAX) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Jacksonville (JAX)

Frontier Airlines • Coach
Save 100% on your flight
Price was $890, price is now $613 per person
$613
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (436 reviews)

Apr 23 - Apr 28

5 night stay

Jacksonville (JAX) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Jacksonville (JAX)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,184, price is now $857 per person
$857
per person
found 9 hours ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

Kimpton Gray Hotel by IHG
4.5-star property

Kimpton Gray Hotel by IHG

9.2/10 Wonderful! (1,000 reviews)

Apr 23 - Apr 28

5 night stay

Jacksonville (JAX) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Jacksonville (JAX)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,241, price is now $914 per person
$914
per person
found 9 hours ago
I absolutely loved my stay at this property! Everything—from the warm, welcoming atmosphere to the beautifully maintained rooms—made the experience unforgettable. The staff were incredibly kind, and every detail felt thoughtfully designed for comfort. I can’t wait to come back!

Reviewed on Nov 21, 2025

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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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Get Bargain Fares for St. Augustine to Chicago Flights

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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.

More Destinations

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.