$35 Cheap flight deals from Chicago (CHI) to Casselberry (ORL)

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This Weekend's Flight Deals from Chicago to Casselberry

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 18 - Thu, Apr 23
ORD
O'Hare Intl.
MCO
Orlando Intl.
$178 Roundtrip, found 3 hours ago
$178
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Apr 18 from O'Hare Intl. to Orlando Intl., returning Thu, Apr 23, priced at $178 found 3 hours ago
Sun, Apr 19 - Sat, Apr 25
MDW
Midway Intl.
MCO
Orlando Intl.
$205 Roundtrip, found 16 hours ago
$205
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sun, Apr 19 from Midway Intl. to Orlando Intl., returning Sat, Apr 25, priced at $205 found 16 hours ago
Sat, Apr 18 - Thu, Apr 23
RFD
Greater Rockford
MCO
Orlando Intl.
$389 Roundtrip, found 2 days ago
$389
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Apr 18 from Greater Rockford to Orlando Intl., returning Thu, Apr 23, priced at $389 found 2 days ago

Airfares from $35 One Way, $69 Round Trip from Chicago to Casselberry

Prices starting at $69 for return flights and $35 for one-way flights to Casselberry 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, May 2 - Fri, May 8
MDW
Chicago
MCO
Orlando
$69 Roundtrip, found 1 day ago
$69
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 2 from Chicago to Orlando, returning Fri, May 8, priced at $69 found 1 day ago
Mon, Apr 27 - Wed, May 6
ORD
Chicago
MCO
Orlando
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Apr 27 from Chicago to Orlando, returning Wed, May 6, priced at $87 found 1 day ago
Wed, May 27 - Tue, Jun 2
RFD
Rockford
MCO
Orlando
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, May 27 from Rockford to Orlando, returning Tue, Jun 2, priced at $169 found 2 days ago
Wed, Jun 10 - Tue, Jun 16
ORD
Chicago
MCO
Orlando
$169 Roundtrip, found 10 hours ago
$169
Roundtrip
found 10 hours ago
Select United flight, departing Wed, Jun 10 from Chicago to Orlando, returning Tue, Jun 16, priced at $169 found 10 hours ago
Wed, Jun 10 - Tue, Jun 16
MDW
Chicago
MCO
Orlando
$169 Roundtrip, found 10 hours ago
$169
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Wed, Jun 10 from Chicago to Orlando, returning Tue, Jun 16, priced at $169 found 10 hours ago

Casselberry economy 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

8.2/10 Very Good! (1,554 reviews)

May 12 - May 15

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $422, price is now $231 per person
$231
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 Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

8/10 Very Good! (1,836 reviews)

May 18 - May 23

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $565, price is now $245 per person
$245
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 Towers Resort
3.5-star property

Westgate Towers Resort

8.6/10 Excellent! (1,002 reviews)

May 18 - May 23

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $554, price is now $260 per person
$260
per person
found 1 day ago
Great place and very clean. They provide so many amenities

Reviewed on Aug 24, 2025

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More About Flying To Casselberry from Chicago

Route Information for Flights from Chicago to Casselberry

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

Chicago to Casselberry

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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.