$48 Cheap flight deals from Chicago (CHI) to Port Orange (DAB)

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This Weekend's Flight Deals from Chicago to Port Orange

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, Oct 23 - Wed, Oct 28
RFD
Greater Rockford
SFB
Orlando Sanford Intl.
$241 Roundtrip, found 2 hours ago
$241
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Fri, Oct 23 from Greater Rockford to Orlando Sanford Intl., returning Wed, Oct 28, priced at $241 found 2 hours ago

Airfares from $48 One Way, $112 Round Trip from Chicago to Port Orange

Prices starting at $112 for return flights and $48 for one-way flights to Port Orange 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 11 - Thu, Jan 21
RFD
Rockford
SFB
Orlando
$112 Roundtrip, found 4 hours ago
$112
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Mon, Jan 11 from Rockford to Orlando, returning Thu, Jan 21, priced at $112 found 4 hours ago
Mon, Jan 11 - Thu, Jan 21
RFD
Rockford
SFB
Orlando
$126 Roundtrip, found 5 days ago
$126
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Mon, Jan 11 from Rockford to Orlando, returning Thu, Jan 21, priced at $126 found 5 days ago
Mon, Jan 11 - Thu, Jan 14
RFD
Rockford
SFB
Orlando
$134 Roundtrip, found 5 days ago
$134
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Mon, Jan 11 from Rockford to Orlando, returning Thu, Jan 14, priced at $134 found 5 days ago
Fri, Jan 22 - Thu, Jan 28
RFD
Rockford
SFB
Orlando
$136 Roundtrip, found 2 days ago
$136
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Fri, Jan 22 from Rockford to Orlando, returning Thu, Jan 28, priced at $136 found 2 days ago
Mon, Jan 25 - Fri, Jan 29
RFD
Rockford
SFB
Orlando
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Mon, Jan 25 from Rockford to Orlando, returning Fri, Jan 29, priced at $142 found 2 days ago

Port Orange economy 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! (1,001 reviews)

Nov 21 - Nov 25

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,319, price is now $803 per person
$803
per person
found 1 day ago
This place was fantastic to stay at. We had a two bedroom cottage, the facilities were fantastic. All bedrooms ensuite, TVs in every room. Full kitchen and living room. Hot tub. Great pool nearby and sunset walk is five minutes walk away. They had live music in most nights and there is a lot of different food and drink places there.

Reviewed on Oct 15, 2026

Disney's Animal Kingdom Lodge
4.5-star property

Disney's Animal Kingdom Lodge

9/10 Wonderful! (1,004 reviews)

Nov 27 - Nov 30

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,864, price is now $1,034 per person
$1,034
per person
found 1 day ago
The Animal Kingdom Lodge is just beautiful. We had a room with a view of the animals which we loved. The restaurants were excellent and the entire staff was very friendly and helpful.

Reviewed on Oct 9, 2026

Villa 1565
3.0-star property

Villa 1565

7.6/10 Good! (2,074 reviews)

Nov 21 - Nov 29

8 night stay

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,616, price is now $1,015 per person
$1,015
per person
found 4 hours ago
This an old, I mean VERY old, property which needs complete redo. The building is OLD, the maintenance is terrible. It is a shame that this place is still in business. Our room was full of dust. Even the walls were full of dust. Mosquitos were flying out of dust. The sink drain was clogged (the drain was cleaned up after we let them know). Door to the unit did not close well and mosquitos could come in from around the closed door. The location is superb (the only plus). We will never, ever, go back to this place. I really wish I could be more positive, but I couldn’t. PK

Reviewed on Oct 16, 2026

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Port Orange packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
2.0-star property

Seasons Florida Resort

9/10 Wonderful! (3,974 reviews)

Dec 10 - Dec 14

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $827, price is now $557 per person
$557
per person
found 1 day ago

Margaritaville Cottages Orlando by Vstays with H2O Waterpark
4.0-star property

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

9.2/10 Wonderful! (1,001 reviews)

Dec 10 - Dec 14

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,412, price is now $957 per person
$957
per person
found 1 day ago
This place was fantastic to stay at. We had a two bedroom cottage, the facilities were fantastic. All bedrooms ensuite, TVs in every room. Full kitchen and living room. Hot tub. Great pool nearby and sunset walk is five minutes walk away. They had live music in most nights and there is a lot of different food and drink places there.

Reviewed on Oct 15, 2026

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,213 reviews)

Dec 10 - Dec 14

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $1,110, price is now $760 per person
$760
per person
found 1 day ago
Nice property, clean hotel! Sometimes loud, with the ambulances and helicopters going to the hospital, directly across the street. Beds are soft, so not very comfortable, wish they were more firm. Overall, nice stay though!

Reviewed on Oct 15, 2026

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More About Flying To Port Orange from Chicago

Route Information for Flights from Chicago to Port Orange

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

Chicago to Port Orange

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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.