$54 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, Jul 4 - Sun, Jul 5
ORD
O'Hare Intl.
MCO
Orlando Intl.
$328 Roundtrip, found 3 hours ago
$328
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Jul 4 from O'Hare Intl. to Orlando Intl., returning Sun, Jul 5, priced at $328 found 3 hours ago
Sat, Jul 4 - Fri, Jul 10
MDW
Midway Intl.
MCO
Orlando Intl.
$346 Roundtrip, found 1 day ago
$346
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jul 4 from Midway Intl. to Orlando Intl., returning Fri, Jul 10, priced at $346 found 1 day ago

Airfares from $54 One Way, $111 Round Trip from Chicago to Casselberry

Prices starting at $111 for return flights and $54 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.

Tue, Aug 18 - Tue, Aug 25
ORD
Chicago
MCO
Orlando
$111 Roundtrip, just found
$111
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Aug 18 from Chicago to Orlando, returning Tue, Aug 25, priced at $111 just found
Sat, Sep 26 - Tue, Sep 29
ORD
Chicago
MCO
Orlando
$118 Roundtrip, found 13 hours ago
$118
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Chicago to Orlando, returning Tue, Sep 29, priced at $118 found 13 hours ago
Tue, Sep 8 - Tue, Sep 15
MDW
Chicago
MCO
Orlando
$210 Roundtrip, found 5 hours ago
$210
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Sep 8 from Chicago to Orlando, returning Tue, Sep 15, priced at $210 found 5 hours ago
Sat, Sep 5 - Tue, Sep 8
RFD
Rockford
MCO
Orlando
$216 Roundtrip, found 2 hours ago
$216
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Sep 5 from Rockford to Orlando, returning Tue, Sep 8, priced at $216 found 2 hours ago
Sat, Sep 5 - Tue, Sep 8
MDW
Chicago
MCO
Orlando
$217 Roundtrip, found 2 hours ago
$217
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Chicago to Orlando, returning Tue, Sep 8, priced at $217 found 2 hours ago

Casselberry economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort
3.5-star property

Westgate Towers Resort

8.6/10 Excellent! (1,002 reviews)

Aug 12 - Aug 15

3 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 $444, price is now $263 per person
$263
per person
found 1 day ago
There were no closets for it to be named a Villa studio. No utensils. There was a door in the bathroom by the toilet so super awkward to get to the shower. The TV would turn off on its on while watching it. Floors were not mopped. I had to were slippers the entire time. I heard every noise from the street even though we were on the fifth floor. Our clothes lived out of the suitcases due to no hanging storage available. No comforter in the beds. Not sure what the non upgraded room looked like? Just a weird room and not well planned out for it to be called a Villa studio. Bed frame not connected to the headboard and rolled around while sleeping and turning

Reviewed on Jun 24, 2026

Westgate Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

8.2/10 Very Good! (1,977 reviews)

Aug 15 - Aug 21

6 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • Non-stop • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $788, price is now $414 per person
$414
per person
found 19 hours ago
Great property was very nice. Couldn’t use amenities due to rainy weather. But the condo was great with space. I would rebook.

Reviewed on Jul 1, 2026

Seasons Florida Resort
2.0-star property

Seasons Florida Resort

9/10 Wonderful! (3,647 reviews)

Aug 11 - Aug 15

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 $476, price is now $282 per person
$282
per person
found 1 day ago
The rooms and property were very clean. The wife and I really liked this hotel. It was insanely quiet. Felt like the only ones there. Felt safe and felt our items were secure. Loved our stay. Stay was super nice. This is a hidden gem. A/C worked great. Shower got super hot. Iron with board. Bed was comfortable and good pillows. Not a ton to do if you have children but we are empty nesters and it was the perfect location for all theme parks and local places to eat and close to several places to get things like dollar store, CVS, Walmart, and Ross. Plus several places to eat nearby. So if you want clean, quiet and good location with friendly staff this is your place…

Reviewed on Jul 1, 2026

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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.