$50 Cheap flight deals from Chicago (CHI) to Ponte Vedra Beach (JAX)

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This Weekend's Flight Deals from Chicago to Ponte Vedra Beach

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 22 - Tue, Aug 25
ORD
O'Hare Intl.
MCO
Orlando Intl.
$209 Roundtrip, found 5 hours ago
$209
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Aug 22 from O'Hare Intl. to Orlando Intl., returning Tue, Aug 25, priced at $209 found 5 hours ago
Sat, Aug 22 - Sun, Aug 23
MDW
Midway Intl.
JAX
Jacksonville Intl.
$304 Roundtrip, found 5 days ago
$304
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 22 from Midway Intl. to Jacksonville Intl., returning Sun, Aug 23, priced at $304 found 5 days ago
Fri, Aug 21 - Sun, Aug 23
MDW
Midway Intl.
MCO
Orlando Intl.
$340 Roundtrip, found 3 hours ago
$340
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Aug 21 from Midway Intl. to Orlando Intl., returning Sun, Aug 23, priced at $340 found 3 hours ago
Fri, Aug 21 - Sun, Aug 23
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$345 Roundtrip, found 1 day ago
$345
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 21 from O'Hare Intl. to Jacksonville Intl., returning Sun, Aug 23, priced at $345 found 1 day ago

Airfares from $50 One Way, $98 Round Trip from Chicago to Ponte Vedra Beach

Prices starting at $98 for return flights and $50 for one-way flights to Ponte Vedra Beach 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, Oct 31 - Sat, Nov 7
ORD
Chicago
MCO
Orlando
$98 Roundtrip, found 2 hours ago
$98
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Oct 31 from Chicago to Orlando, returning Sat, Nov 7, priced at $98 found 2 hours ago
Thu, Oct 22 - Mon, Oct 26
ORD
Chicago
JAX
Jacksonville
$142 Roundtrip, found 13 hours ago
$142
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Chicago to Jacksonville, returning Mon, Oct 26, priced at $142 found 13 hours ago
Thu, Sep 3 - Thu, Sep 10
MDW
Chicago
JAX
Jacksonville
$144 Roundtrip, found 19 hours ago
$144
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Sep 3 from Chicago to Jacksonville, returning Thu, Sep 10, priced at $144 found 19 hours ago
Thu, Oct 29 - Fri, Oct 30
MDW
Chicago
JAX
Jacksonville
$190 Roundtrip, found 4 hours ago
$190
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Oct 29 from Chicago to Jacksonville, returning Fri, Oct 30, priced at $190 found 4 hours ago
Sat, Oct 31 - Tue, Nov 3
ORD
Chicago
MCO
Orlando
$195 Roundtrip, found 6 hours ago
$195
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Oct 31 from Chicago to Orlando, returning Tue, Nov 3, priced at $195 found 6 hours ago

Ponte Vedra Beach economy flight packages

Price found within the past 48 hours. Click for updated prices.
Blue Tree Resort at Lake Buena Vista
3.0-star property

Blue Tree Resort at Lake Buena Vista

8.6/10 Excellent! (2,036 reviews)

Sep 17 - Sep 22

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $430, price is now $252 per person
$252
per person
found 1 day ago
Extremely disappointing experience. The room was not cleaned properly, especially the bathroom, which was in an unacceptable condition. The front desk also provided misleading information when I asked for assistance. Poor housekeeping and poor customer service. Completely unacceptable and not a place I would stay again

Reviewed on Aug 9, 2026

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0-star property

Regal Oaks Resort Vacation Townhomes by IDILIQ

8.4/10 Very Good! (3,194 reviews)

Sep 19 - Sep 27

8 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $717, price is now $405 per person
$405
per person
found 1 day ago
This is the third time I have stayed at Regal Oaks. I highly recommend it. The only issue I had with the property was the washing machine leaked when I was doing my laundry and it made a very loud noise while spinning. I also noticed the shower upstairs must have a leak as evidenced by the crack in the living room ceiling and there was some water on the living room floor after I took a shower. Other than that, I love the facilities. It's convenient to all the attractions. I will continue to book with Regal Oaks for future trips. The staff were all very pleasant.

Reviewed on Aug 12, 2026

Magic Village Yards, Trademark Collection by Wyndham
4.0-star property

Magic Village Yards, Trademark Collection by Wyndham

9/10 Wonderful! (1,196 reviews)

Sep 17 - Sep 21

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
Price was $949, price is now $556 per person
$556
per person
found 1 day ago
clean room and staff

Reviewed on Aug 13, 2026

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Ponte Vedra Beach first class flight packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
4.0-star property

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

9.2/10 Wonderful! (1,005 reviews)

Sep 18 - Sep 21

3 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • FirstClass
Price was $1,587, price is now $1,213 per person
$1,213
per person
found 1 day ago
Absolutely great place to stay. No complaints. Our condo had everything we needed. A beautiful place to stay and free access daily to the water park was awesome. Plenty of places to eat and shop super close to the resort. A definite smart choice way better than a hotel. Making plans with friends for the next trip.

Reviewed on Aug 10, 2026

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,178 reviews)

Oct 3 - Oct 10

7 night stay

Chicago (CHI) to Orlando (MCO)

United • FirstClass

Orlando (MCO) to Chicago (CHI)

Delta • FirstClass
Price was $1,824, price is now $1,376 per person
$1,376
per person
found 18 hours ago

Reunion Resort & Golf Club
5.0-star property

Reunion Resort & Golf Club

8.8/10 Excellent! (1,602 reviews)

Oct 3 - Oct 10

7 night stay

Chicago (CHI) to Orlando (MCO)

United • FirstClass

Orlando (MCO) to Chicago (CHI)

Delta • FirstClass
Price was $1,908, price is now $1,453 per person
$1,453
per person
found 18 hours ago
The rooms are clean. The amenities are excellent. The hospitality of the transports are great.

Reviewed on Aug 13, 2026

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More About Flying To Ponte Vedra Beach from Chicago

Route Information for Flights from Chicago to Ponte Vedra Beach

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

Chicago to Ponte Vedra Beach

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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.