$60 Cheap flight deals from Chicago (CHI) to Northeast Florida (JAX)

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This Weekend's Flight Deals from Chicago to Northeast Florida

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.

Fri, Nov 14 - Sat, Nov 15
MDW
Midway Intl.
JAX
Jacksonville Intl.
$301 Roundtrip, just found
$301
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 14 from Midway Intl. to Jacksonville Intl., returning Sat, Nov 15, priced at $301 just found
Sat, Nov 15 - Mon, Nov 24
ORD
O'Hare Intl.
GNV
Gainesville Regional
$387 Roundtrip, found 1 day ago
$387
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 15 from O'Hare Intl. to Gainesville Regional, returning Mon, Nov 24, priced at $387 found 1 day ago
Sun, Nov 16 - Sat, Nov 22
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$420 Roundtrip, found 1 hour ago
$420
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Nov 16 from O'Hare Intl. to Jacksonville Intl., returning Sat, Nov 22, priced at $420 found 1 hour ago
Sat, Nov 15 - Mon, Nov 17
MDW
Midway Intl.
GNV
Gainesville Regional
$504 Roundtrip, found 1 day ago
$504
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 15 from Midway Intl. to Gainesville Regional, returning Mon, Nov 17, priced at $504 found 1 day ago

Airfares from $60 One Way, $120 Round Trip from Chicago to Northeast Florida

Prices starting at $120 for return flights and $60 for one-way flights to Northeast Florida were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jan 26 - Mon, Feb 2
MDW
Chicago
JAX
Jacksonville
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jan 26 from Chicago to Jacksonville, returning Mon, Feb 2, priced at $120 found 3 days ago
Mon, Feb 2 - Wed, Feb 4
ORD
Chicago
JAX
Jacksonville
$227 Roundtrip, found 2 days ago
$227
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Feb 2 from Chicago to Jacksonville, returning Wed, Feb 4, priced at $227 found 2 days ago
Fri, Dec 5 - Tue, Dec 9
ORD
Chicago
DAB
Daytona Beach
$273 Roundtrip, found 4 days ago
$273
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Dec 5 from Chicago to Daytona Beach, returning Tue, Dec 9, priced at $273 found 4 days ago
Sat, Feb 14 - Sat, Feb 21
ORD
Chicago
JAX
Jacksonville
$277 Roundtrip, found 19 hours ago
$277
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Feb 14 from Chicago to Jacksonville, returning Sat, Feb 21, priced at $277 found 19 hours ago
Tue, Mar 3 - Tue, Mar 10
MDW
Chicago
DAB
Daytona Beach
$294 Roundtrip, found 20 hours ago
$294
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Mar 3 from Chicago to Daytona Beach, returning Tue, Mar 10, priced at $294 found 20 hours ago

Northeast Florida economy flight packages

Price found within the past 48 hours. Click for updated prices.
Equus Inn Ocala
2.5-star property

Equus Inn Ocala

9/10 Wonderful! (1,638 reviews)

Dec 23 - Dec 28

5 night stay

Chicago (CHI) to Gainesville (GNV)

Spirit Airlines • Coach

Gainesville (GNV) to Chicago (CHI)

Frontier Airlines • Coach
Price was $532, price is now $400 per person
$400
per person
found 1 day ago
Room was clean however the Moise from the street was not so good

Reviewed on Oct 29, 2025

Hammock Beach Golf Resort & Spa
4.0-star property

Hammock Beach Golf Resort & Spa

8.6/10 Excellent! (1,004 reviews)

Dec 23 - Dec 28

5 night stay

Chicago (CHI) to Daytona Beach (DAB)

Spirit Airlines • Coach

Daytona Beach (DAB) to Chicago (CHI)

Frontier Airlines • Coach
Price was $1,421, price is now $1,060 per person
$1,060
per person
found 1 day ago
The bed was incredibly uncomfortable with a huge sag in the middle, the sheets were not plush and just stiff. We walked into the steakhouse ahead of two other parties and we were asked to wait because they had to “seat members first.” They made us feel unseen the whole time. They also nickel and dimed us. I have never had to pay for a beach chair at a resort where I’m paying a resort fee. Then the putting green was poorly maintained. The food everywhere was average. The buildings in general need better maintenance and the cleaning staff are not cleaning because the bathroom floors were black all over the resort. Only the room cleaner at the lodge looked like she was working hard. The ice maker was leaking under the carpet into our room. The lodge doors don’t close they just slam shut all night long. Lastly the hot tub was lukewarm. The property is nice but feels poorly managed and maintained.

Reviewed on Nov 2, 2025

The Equestrian Hotel
5.0-star property

The Equestrian Hotel

9.8/10 Exceptional! (555 reviews)

Jan 4 - Jan 7

3 night stay

Chicago (CHI) to Gainesville (GNV)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $847, price is now $650 per person
$650
per person
found 1 day ago
This property is an amazing jewel. The grounds are immense and truly a horse-lovers paradise if you are there to participate or watch an event. The lobby was classy, staff competent, and Stirrups restaurant was fabulous (a bit pricey but I expected that). My room was beautiful, large, and comfy. The only disappointment was that there was no in-room coffee maker but free coffee was offered each morning on the 5th floor. I attended an independent event in one of the property’s Expo buildings. It was super clean, spacious, and had adequate bathrooms and parking. I would not hesitate to stay there again.

Reviewed on Apr 24, 2023

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More About Flying To Northeast Florida from Chicago

Route Information for Flights from Chicago to Northeast Florida

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

Chicago to Northeast Florida

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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.