$69 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, Aug 29 - Wed, Sep 2
MCO
Orlando Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 3 hours ago
$199
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando Intl. to O'Hare Intl., returning Wed, Sep 2, priced at $199 found 3 hours ago
Sun, Aug 30 - Sun, Sep 6
MCO
Orlando Intl.
MDW
Midway Intl.
$334 Roundtrip, found 2 hours ago
$334
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Orlando Intl. to Midway Intl., returning Sun, Sep 6, priced at $334 found 2 hours ago
Sun, Aug 30 - Wed, Sep 2
JAX
Jacksonville Intl.
MDW
Midway Intl.
$345 Roundtrip, found 5 days ago
$345
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Jacksonville Intl. to Midway Intl., returning Wed, Sep 2, priced at $345 found 5 days ago
Sun, Aug 30 - Tue, Sep 1
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$355 Roundtrip, found 16 hours ago
$355
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Jacksonville Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $355 found 16 hours ago

Airfares from $69 One Way, $136 Round Trip from St. Augustine to Chicago

Prices starting at $136 for return flights and $69 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.

Wed, Oct 14 - Mon, Oct 19
MCO
Orlando
ORD
Chicago
$136 Roundtrip, found 3 hours ago
$136
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Orlando to Chicago, returning Mon, Oct 19, priced at $136 found 3 hours ago
Wed, Nov 11 - Tue, Nov 17
JAX
Jacksonville
MDW
Chicago
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Nov 11 from Jacksonville to Chicago, returning Tue, Nov 17, priced at $178 found 1 day ago
Thu, Oct 29 - Mon, Nov 2
JAX
Jacksonville
ORD
Chicago
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 29 from Jacksonville to Chicago, returning Mon, Nov 2, priced at $188 found 1 day ago
Tue, Sep 22 - Sat, Sep 26
JAX
Jacksonville
RFD
Rockford
$196 Roundtrip, found 19 hours ago
$196
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Tue, Sep 22 from Jacksonville to Rockford, returning Sat, Sep 26, priced at $196 found 19 hours ago
Mon, Dec 21 - Thu, Dec 24
JAX
Jacksonville
MDW
Chicago
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Dec 21 from Jacksonville to Chicago, returning Thu, Dec 24, priced at $197 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! (5,045 reviews)

Oct 21 - Oct 24

3 night stay

Jacksonville (JAX) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,205, price is now $804 per person
$804
per person
found 1 day ago
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.

Reviewed on Aug 26, 2026

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,553 reviews)

Oct 21 - Oct 24

3 night stay

Jacksonville (JAX) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,466, price is now $893 per person
$893
per person
found 1 day ago

The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,339 reviews)

Oct 9 - Oct 13

4 night stay

Jacksonville (JAX) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Jacksonville (JAX)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,936, price is now $1,368 per person
$1,368
per person
found 18 hours ago

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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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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.