$43 Cheap flight deals from Chicago (CHI) to Winter Park (ORL)

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This Weekend's Flight Deals from Chicago to Winter Park

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, Jun 6 - Sat, Jun 13
ORD
O'Hare Intl.
MCO
Orlando Intl.
$286 Roundtrip, just found
$286
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jun 6 from O'Hare Intl. to Orlando Intl., returning Sat, Jun 13, priced at $286 just found
Sat, Jun 6 - Sat, Jun 13
MDW
Midway Intl.
MCO
Orlando Intl.
$304 Roundtrip, found 4 days ago
$304
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Midway Intl. to Orlando Intl., returning Sat, Jun 13, priced at $304 found 4 days ago

Airfares from $43 One Way, $82 Round Trip from Chicago to Winter Park

Prices starting at $82 for return flights and $43 for one-way flights to Winter Park 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, Oct 6 - Tue, Oct 13
ORD
Chicago
MCO
Orlando
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Oct 6 from Chicago to Orlando, returning Tue, Oct 13, priced at $82 just found
Mon, Sep 28 - Tue, Oct 6
ORD
Chicago
MCO
Orlando
$98 Roundtrip, found 11 hours ago
$98
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Chicago to Orlando, returning Tue, Oct 6, priced at $98 found 11 hours ago
Mon, Sep 28 - Mon, Oct 5
ORD
Chicago
MCO
Orlando
$114 Roundtrip, found 11 hours ago
$114
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Chicago to Orlando, returning Mon, Oct 5, priced at $114 found 11 hours ago
Tue, Jul 28 - Tue, Aug 4
RFD
Rockford
MCO
Orlando
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jul 28 from Rockford to Orlando, returning Tue, Aug 4, priced at $171 found 4 days ago
Wed, Oct 28 - Sat, Oct 31
MDW
Chicago
MCO
Orlando
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Chicago to Orlando, returning Sat, Oct 31, priced at $187 found 5 days ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,257 reviews)

Jul 27 - Jul 30

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $854, price is now $492 per person
$492
per person
found 1 day ago
The property is nice and convenient. I took a star off because my whole party agreed that the beds were not comfortable. I don’t remember a worse mattress. Other than that, great place that was clean and spacious. Great shower pressure.

Reviewed on Apr 3, 2026

Boardwalk Inn and Suites
2.5-star property

Boardwalk Inn and Suites

8.4/10 Very Good! (1,842 reviews)

Jul 3 - Jul 11

8 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,090, price is now $583 per person
$583
per person
found 1 day ago
Absolutely fantastic.

Reviewed on Feb 9, 2026

Hilton Daytona Beach Oceanfront Resort
4.0-star property

Hilton Daytona Beach Oceanfront Resort

7.4/10 Good! (4,859 reviews)

Jul 3 - Jul 11

8 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,000, price is now $610 per person
$610
per person
found 1 day ago
Great place and great location and super perfect for a great Daytona Getaway

Reviewed on Apr 27, 2026

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Winter Park first class flight packages

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

Seasons Florida Resort

9/10 Wonderful! (3,557 reviews)

Jul 25 - Aug 1

7 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,163, price is now $854 per person
$854
per person
found 3 hours ago
Air conditioning LOUD. Works ok. clean room

Reviewed on Jun 1, 2026

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

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (6,490 reviews)

Jul 25 - Aug 1

7 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,583, price is now $1,086 per person
$1,086
per person
found 3 hours ago
Everything was average. I chose this hotel because of the kids’ pool and water park, not knowing that access to the water park required an additional charge on top of the stay. This information was not disclosed until our arrival. It would have been helpful to know about these extra fees beforehand, as it may have influenced my decision when choosing this hotel.

Reviewed on May 31, 2026

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

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

9.2/10 Wonderful! (1,003 reviews)

Jul 25 - Aug 1

7 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • FirstClass
Save 100% on your flight
Price was $2,530, price is now $1,771 per person
$1,771
per person
found 3 hours ago
This place is amazing! I just wish we had more time to enjoy the resort.

Reviewed on Apr 1, 2026

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More About Flying To Winter Park from Chicago

Route Information for Flights from Chicago to Winter Park

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

Chicago to Winter Park

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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.