$29 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.

Sun, Apr 19 - Fri, Apr 24
ORD
O'Hare Intl.
MCO
Orlando Intl.
$141 Roundtrip, found 5 hours ago
$141
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Sun, Apr 19 from O'Hare Intl. to Orlando Intl., returning Fri, Apr 24, priced at $141 found 5 hours ago
Sun, Apr 19 - Sat, Apr 25
MDW
Midway Intl.
MCO
Orlando Intl.
$205 Roundtrip, found 3 days ago
$205
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Apr 19 from Midway Intl. to Orlando Intl., returning Sat, Apr 25, priced at $205 found 3 days ago
Sat, Apr 18 - Thu, Apr 23
RFD
Greater Rockford
MCO
Orlando Intl.
$389 Roundtrip, found 4 days ago
$389
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Apr 18 from Greater Rockford to Orlando Intl., returning Thu, Apr 23, priced at $389 found 4 days ago

Airfares from $29 One Way, $69 Round Trip from Chicago to Winter Park

Prices starting at $69 for return flights and $29 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.

Sat, May 2 - Fri, May 8
MDW
Chicago
MCO
Orlando
$69 Roundtrip, found 4 days ago
$69
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, May 2 from Chicago to Orlando, returning Fri, May 8, priced at $69 found 4 days ago
Mon, Apr 20 - Thu, Apr 23
ORD
Chicago
MCO
Orlando
$99 Roundtrip, found 9 hours ago
$99
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Mon, Apr 20 from Chicago to Orlando, returning Thu, Apr 23, priced at $99 found 9 hours ago
Wed, May 27 - Tue, Jun 2
RFD
Rockford
MCO
Orlando
$169 Roundtrip, found 4 days ago
$169
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, May 27 from Rockford to Orlando, returning Tue, Jun 2, priced at $169 found 4 days ago
Wed, May 27 - Tue, Jun 2
ORD
Chicago
MCO
Orlando
$169 Roundtrip, found 5 hours ago
$169
Roundtrip
found 5 hours ago
Select United flight, departing Wed, May 27 from Chicago to Orlando, returning Tue, Jun 2, priced at $169 found 5 hours ago
Wed, May 27 - Tue, Jun 2
ORD
Chicago
MCO
Orlando
$169 Roundtrip, found 4 hours ago
$169
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Wed, May 27 from Chicago to Orlando, returning Tue, Jun 2, priced at $169 found 4 hours 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! (1,233 reviews)

May 20 - May 23

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $611, price is now $301 per person
$301
per person
found 1 day ago
Great location had a good time

Reviewed on Dec 28, 2025

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

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

May 29 - Jun 2

4 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
Save 100% on your flight
Price was $568, price is now $303 per person
$303
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

Boardwalk Inn and Suites
2.5-star property

Boardwalk Inn and Suites

8.4/10 Very Good! (1,750 reviews)

Jun 6 - Jun 11

5 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $656, price is now $388 per person
$388
per person
found 1 day ago
Absolutely fantastic.

Reviewed on Feb 9, 2026

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Winter Park packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Kissimmee-Lake Buena Vista South
3.0-star property

Comfort Inn Kissimmee-Lake Buena Vista South

7.4/10 Good! (1,003 reviews)

May 26 - May 29

3 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $415, price is now $354 per person
$354
per person
found 1 day ago
Room wasna lil dirty but everythingnelse good

Reviewed on Feb 1, 2026

Encore Resort and Water Park at Reunion by Rentyl
5.0-star property

Encore Resort and Water Park at Reunion by Rentyl

8.2/10 Very Good! (1,007 reviews)

May 26 - May 29

3 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,010, price is now $854 per person
$854
per person
found 1 day ago
Very nice property! Convenient to grocery shopping and Disney attractions. Customer service was very helpful. Bartender at pool attitude was not pleasant and drinks were weak along with prices too high for the service. Overall great service!

Reviewed on Jun 22, 2024

Orlando Vacation Rooms
3.0-star property

Orlando Vacation Rooms

8.2/10 Very Good! (178 reviews)

May 26 - May 29

3 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $394, price is now $355 per person
$355
per person
found 1 day ago
I think for the money, this place is great. It appears to have been remodeled very cleanly and simply. The check in was quick and easy. Room was nice and clean. Bed was nice and AC was perfect. The shower was good. I was able to walk to Macaroni Grill for dinner, which was nice after a 7 hour drive. I had my choice of 4 or 5 restaurants I could have walked to, which was nice. Only 10 miles to Mecum car auction. Easy out this morning. I will be back in 2025.

Reviewed on Jan 14, 2024

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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.