$40 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.

Sat, Oct 4 - Wed, Oct 8
ORD
O'Hare Intl.
MCO
Orlando Intl.
$104 Roundtrip, just found
$104
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Oct 4 from O'Hare Intl. to Orlando Intl., returning Wed, Oct 8, priced at $104 just found
Sun, Oct 5 - Mon, Oct 6
MDW
Midway Intl.
MCO
Orlando Intl.
$156 Roundtrip, found 17 hours ago
$156
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sun, Oct 5 from Midway Intl. to Orlando Intl., returning Mon, Oct 6, priced at $156 found 17 hours ago

Airfares from $40 One Way, $81 Round Trip from Chicago to Winter Garden

Prices starting at $81 for return flights and $40 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.

Mon, Oct 20 - Wed, Oct 22
ORD
Chicago
MCO
Orlando
$81 Roundtrip, found 23 hours ago
$81
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Chicago to Orlando, returning Wed, Oct 22, priced at $81 found 23 hours ago
Sat, Oct 25 - Sat, Nov 1
MDW
Chicago
MCO
Orlando
$94 Roundtrip, just found
$94
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 25 from Chicago to Orlando, returning Sat, Nov 1, priced at $94 just found
Sat, Dec 6 - Sat, Dec 13
RFD
Rockford
MCO
Orlando
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 6 from Rockford to Orlando, returning Sat, Dec 13, priced at $157 found 3 days ago
Sat, Nov 15 - Tue, Nov 18
ORD
Chicago
MCO
Orlando
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Nov 15 from Chicago to Orlando, returning Tue, Nov 18, priced at $157 just found
Sun, Feb 1 - Tue, Feb 10
ORD
Chicago
MCO
Orlando
$227 Roundtrip, just found
$227
Roundtrip
just found
Select JetBlue Airways flight, departing Sun, Feb 1 from Chicago to Orlando, returning Tue, Feb 10, priced at $227 just found

Winter Garden 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

8/10 Very Good! (1,360 reviews)

Nov 1 - Nov 4

3 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $400, price is now $213 per person
$213
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

The Shores Resort & Spa
4.0-star property

The Shores Resort & Spa

9/10 Wonderful! (1,692 reviews)

Nov 13 - Nov 17

4 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $581, price is now $325 per person
$325
per person
found 23 hours ago
Pretty hotel with nice layout and nice rooms. Great restaurant and friendly staff.

Reviewed on Sep 20, 2025

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

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,012 reviews)

Nov 7 - Nov 10

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Non-stop • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $684, price is now $386 per person
$386
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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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
1006 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Azul, Copa Airlines, Gol, Swiss, Air New Zealand, United Airlines, Alaska Airlines, Frontier Airlines, Cathay Pacific, Southwest Airlines, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, British Airways
Earliest Flight Arrival
1:48PM UTC
Latest Flight Arrival
4:35AM UTC

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.