$25 Cheap flight deals from Chicago (CHI) to Winter Garden (ORL)

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This Weekend's Flight Deals from Chicago to Winter Garden

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, Nov 23 - Sun, Nov 23
MDW
Midway Intl.
MCO
Orlando Intl.
$129 Roundtrip, found 5 days ago
$129
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Nov 23 from Midway Intl. to Orlando Intl., returning Sun, Nov 23, priced at $129 found 5 days ago
Sun, Nov 23 - Thu, Nov 27
ORD
O'Hare Intl.
MCO
Orlando Intl.
$151 Roundtrip, found 2 hours ago
$151
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Nov 23 from O'Hare Intl. to Orlando Intl., returning Thu, Nov 27, priced at $151 found 2 hours ago
Fri, Nov 21 - Mon, Nov 24
RFD
Greater Rockford
MCO
Orlando Intl.
$385 Roundtrip, found 1 day ago
$385
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Nov 21 from Greater Rockford to Orlando Intl., returning Mon, Nov 24, priced at $385 found 1 day ago

Airfares from $25 One Way, $84 Round Trip from Chicago to Winter Garden

Prices starting at $84 for return flights and $25 for one-way flights to Winter Garden 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, Jan 31 - Thu, Feb 5
ORD
Chicago
MCO
Orlando
$84 Roundtrip, found 2 hours ago
$84
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Jan 31 from Chicago to Orlando, returning Thu, Feb 5, priced at $84 found 2 hours ago
Sat, Jan 31 - Thu, Feb 5
ORD
Chicago
MCO
Orlando
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select United flight, departing Sat, Jan 31 from Chicago to Orlando, returning Thu, Feb 5, priced at $137 found 2 hours ago
Fri, Feb 20 - Fri, Feb 27
ORD
Chicago
MCO
Orlando
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Fri, Feb 20 from Chicago to Orlando, returning Fri, Feb 27, priced at $137 found 1 hour ago
Sat, Jan 31 - Thu, Feb 5
ORD
Chicago
MCO
Orlando
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Jan 31 from Chicago to Orlando, returning Thu, Feb 5, priced at $137 found 2 hours ago
Wed, Jan 21 - Mon, Jan 26
RFD
Rockford
MCO
Orlando
$139 Roundtrip, found 11 hours ago
$139
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Jan 21 from Rockford to Orlando, returning Mon, Jan 26, priced at $139 found 11 hours ago

Winter Garden economy flight packages

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites
2.5-star property

Boardwalk Inn and Suites

8.4/10 Very Good! (1,492 reviews)

Jan 6 - Jan 10

4 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $350, price is now $183 per person
$183
per person
found 4 hours ago
Great place to stay

Reviewed on Oct 26, 2025

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.2/10 Very Good! (5,210 reviews)

Dec 26 - Jan 1

6 night stay

Chicago (CHI) to Orlando (MCO)

Southwest Airlines • Non-stop • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Price was $2,163, price is now $793 per person
$793
per person
found 1 day ago
I was able to check in at 3:00pm but i had to wait till 4:00 to get my key resulting in a long line just to retrieve my key to my room. The elevator was very slow and needs to be updated. The room was updated with zero rugs but the paint inside the bathroom left much to be desired and the bathroom light came on automatically which was a terrible inconvenience for the other person in the room as they got rudely woken up when i had to use the bathroom in the middle of the night. The ac was loud and kept going on and off and wouldnt stay on and the beds although comfy kept hitting my shin when i got in and out of bed because the mattress didnt fit the bed correctly. The breakfast was ok but no fresh juice or muffins was provided as advertised.

Reviewed on Nov 10, 2025

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,037 reviews)

Dec 22 - Dec 27

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,285, price is now $659 per person
$659
per person
found 1 day ago
The location is conveniently close to Universal, with a nearby 7-Eleven and several restaurants. The room is clean and pleasant, and parking is easily accessible.

Reviewed on Aug 6, 2025

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Winter Garden packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
avid hotel Orlando International Airport by IHG
2.5-star property

avid hotel Orlando International Airport by IHG

9.2/10 Wonderful! (1,930 reviews)

Dec 22 - Dec 27

5 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,020, price is now $961 per person
$961
per person
found 1 day ago
Third time staying an they have not disappointed.

Reviewed on Oct 12, 2025

Walt Disney World Swan
4.0-star property

Walt Disney World Swan

9.2/10 Wonderful! (1,909 reviews)

Dec 22 - Dec 27

5 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,482, price is now $1,465 per person
$1,465
per person
found 1 day ago
Hotel is OK. A bit outdated for the price. Bathroom door was very hard to open or close, cabinet door fell off when the door was opened for the first time. The house keeping did not replenished the tissue box as expected. I had a cold and did not have cleaned tissues to use.

Reviewed on Sep 28, 2025

Walt Disney World Dolphin
4.0-star property

Walt Disney World Dolphin

8.8/10 Excellent! (3,905 reviews)

Dec 22 - Dec 27

5 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,391, price is now $1,376 per person
$1,376
per person
found 1 day ago
Would love to see the Disney characters again

Reviewed on Jul 8, 2025

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Winter Garden first class 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! (1,037 reviews)

Dec 26 - Jan 3

8 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,574, price is now $1,521 per person
$1,521
per person
found 1 day ago
The location is conveniently close to Universal, with a nearby 7-Eleven and several restaurants. The room is clean and pleasant, and parking is easily accessible.

Reviewed on Aug 6, 2025

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,368 reviews)

Dec 25 - Jan 2

8 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,430, price is now $1,665 per person
$1,665
per person
found 17 hours 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

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,019 reviews)

Dec 26 - Jan 3

8 night stay

Chicago (ORD) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,450, price is now $1,943 per person
$1,943
per person
found 1 day ago
Great location for hospital access

Reviewed on Jul 8, 2025

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More About Flying To Winter Garden from Chicago

Route Information for Flights from Chicago to Winter Garden

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

Chicago to Winter Garden

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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.