$36 Cheap flight deals from Chicago (CHI) to Northern Florida (ORL)

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This Weekend's Flight Deals from Chicago to Northern 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.

Sat, Apr 4 - Thu, Apr 9
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Apr 4 from O'Hare Intl. to Pensacola Intl., returning Thu, Apr 9, priced at $183 found 2 days ago
Sat, Apr 4 - Sat, Apr 11
MDW
Midway Intl.
PNS
Pensacola Intl.
$215 Roundtrip, found 6 days ago
$215
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Midway Intl. to Pensacola Intl., returning Sat, Apr 11, priced at $215 found 6 days ago
Sat, Apr 4 - Wed, Apr 8
MDW
Midway Intl.
MCO
Orlando Intl.
$255 Roundtrip, found 1 hour ago
$255
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Midway Intl. to Orlando Intl., returning Wed, Apr 8, priced at $255 found 1 hour ago
Fri, Apr 3 - Sun, Apr 5
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$313 Roundtrip, found 10 hours ago
$313
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Fri, Apr 3 from O'Hare Intl. to Jacksonville Intl., returning Sun, Apr 5, priced at $313 found 10 hours ago

Airfares from $36 One Way, $80 Round Trip from Chicago to Northern Florida

Prices starting at $80 for return flights and $36 for one-way flights to Northern 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, Apr 13 - Mon, Apr 20
MDW
Chicago
MCO
Orlando
$80 Roundtrip, found 19 hours ago
$80
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Mon, Apr 13 from Chicago to Orlando, returning Mon, Apr 20, priced at $80 found 19 hours ago
Mon, Apr 20 - Thu, Apr 23
ORD
Chicago
MCO
Orlando
$81 Roundtrip, just found
$81
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Apr 20 from Chicago to Orlando, returning Thu, Apr 23, priced at $81 just found
Mon, Apr 27 - Thu, Apr 30
MDW
Chicago
JAX
Jacksonville
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Chicago to Jacksonville, returning Thu, Apr 30, priced at $140 found 1 day ago
Mon, Apr 27 - Mon, May 4
ORD
Chicago
JAX
Jacksonville
$140 Roundtrip, found 21 hours ago
$140
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Chicago to Jacksonville, returning Mon, May 4, priced at $140 found 21 hours ago
Mon, Apr 6 - Fri, Apr 10
ORD
Chicago
PNS
Pensacola
$163 Roundtrip, found 23 hours ago
$163
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Mon, Apr 6 from Chicago to Pensacola, returning Fri, Apr 10, priced at $163 found 23 hours ago

Northern Florida economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

8/10 Very Good! (1,820 reviews)

May 10 - May 13

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $438, price is now $257 per person
$257
per person
found 1 day ago
Nice pools and Hot tubs. Room I had needed some updating but was a nice lay out. Could see Disney fireworks from slider!

Reviewed on Feb 16, 2026

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,510 reviews)

May 10 - May 13

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $456, price is now $266 per person
$266
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

Westgate Towers Resort
3.5-star property

Westgate Towers Resort

8.6/10 Excellent! (1,004 reviews)

May 10 - May 13

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $433, price is now $257 per person
$257
per person
found 14 hours ago
Great place and very clean. They provide so many amenities

Reviewed on Aug 24, 2025

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Northern Florida first class flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,510 reviews)

May 24 - May 30

6 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • Roundtrip • FirstClass
Price was $1,448, price is now $1,047 per person
$1,047
per person
just found
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.2/10 Very Good! (5,182 reviews)

May 24 - May 30

6 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • Roundtrip • FirstClass
Price was $2,215, price is now $1,086 per person
$1,086
per person
just found
Gracias excelentes 👌 pronto estare de vuelta bendiciones

Reviewed on Feb 9, 2026

Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (5,960 reviews)

May 24 - May 30

6 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • Roundtrip • FirstClass
Price was $1,521, price is now $1,098 per person
$1,098
per person
just found
We had to get 4 room keys for our door to finally work, however staff was kind and helped us as much as they could.

Reviewed on Feb 12, 2026

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More About Flying To Northern Florida from Chicago

Route Information for Flights from Chicago to Northern Florida

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

Chicago to Northern Florida

If you are looking to get guaranteed low prices for Chicago to Northern Florida flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.

Get Package Savings by Booking Flights and Hotels at the Same Time

Using the Orbitz Matrix display, you can see how much you will save on flights from Chicago to Northern Florida if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.

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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.