$40 Cheap flight deals from Chicago (CHI) to Lake Mary (ORL)

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This Weekend's Flight Deals from Chicago to Lake Mary

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, May 24 - Wed, May 27
RFD
Greater Rockford
MCO
Orlando Intl.
$222 Roundtrip, found 5 hours ago
$222
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sun, May 24 from Greater Rockford to Orlando Intl., returning Wed, May 27, priced at $222 found 5 hours ago
Sun, May 24 - Wed, May 27
MDW
Midway Intl.
MCO
Orlando Intl.
$233 Roundtrip, found 5 hours ago
$233
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sun, May 24 from Midway Intl. to Orlando Intl., returning Wed, May 27, priced at $233 found 5 hours ago
Sat, May 23 - Sun, May 24
ORD
O'Hare Intl.
MCO
Orlando Intl.
$337 Roundtrip, found 1 hour ago
$337
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 23 from O'Hare Intl. to Orlando Intl., returning Sun, May 24, priced at $337 found 1 hour ago

Airfares from $40 One Way, $110 Round Trip from Chicago to Lake Mary

Prices starting at $110 for return flights and $40 for one-way flights to Lake Mary 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 20 - Tue, Oct 27
ORD
Chicago
MCO
Orlando
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Chicago to Orlando, returning Tue, Oct 27, priced at $110 found 1 day ago
Mon, Sep 14 - Tue, Sep 22
ORD
Chicago
MCO
Orlando
$116 Roundtrip, found 2 days ago
$116
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Chicago to Orlando, returning Tue, Sep 22, priced at $116 found 2 days ago
Thu, Aug 13 - Wed, Aug 19
ORD
Chicago
MCO
Orlando
$117 Roundtrip, found 8 hours ago
$117
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Chicago to Orlando, returning Wed, Aug 19, priced at $117 found 8 hours ago
Wed, Aug 19 - Tue, Aug 25
RFD
Rockford
MCO
Orlando
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 19 from Rockford to Orlando, returning Tue, Aug 25, priced at $169 found 2 days ago
Tue, Jul 21 - Tue, Jul 28
MDW
Chicago
MCO
Orlando
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Jul 21 from Chicago to Orlando, returning Tue, Jul 28, priced at $169 found 3 days ago

Lake Mary 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

8.2/10 Very Good! (1,718 reviews)

Jul 1 - Jul 5

4 night stay

Chicago (CHI) to Orlando (MCO)

Southwest Airlines • Non-stop • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $736, price is now $415 per person
$415
per person
found 1 day ago
Everything was good

Reviewed on Apr 15, 2026

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

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (6,417 reviews)

Jun 17 - Jun 23

6 night stay

Chicago (CHI) to Orlando (MCO)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,258, price is now $664 per person
$664
per person
found 1 day ago
Great location to everything as far as food, Walmart, attractions etc. Beds were horrible and the parking at night. The water park only has 2 water slides and a small wave pool. It's a joke to charge guest to come in.

Reviewed on Apr 5, 2026

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

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,254 reviews)

Jun 18 - Jun 21

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $912, price is now $528 per person
$528
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

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Lake Mary packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (6,417 reviews)

Jun 18 - Jun 23

5 night stay

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,362, price is now $882 per person
$882
per person
found 7 hours ago
Great location to everything as far as food, Walmart, attractions etc. Beds were horrible and the parking at night. The water park only has 2 water slides and a small wave pool. It's a joke to charge guest to come in.

Reviewed on Apr 5, 2026

Lake Buena Vista Resort Village & Spa
4.0-star property

Lake Buena Vista Resort Village & Spa

8.4/10 Very Good! (9,864 reviews)

Jun 18 - Jun 23

5 night stay

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,199, price is now $952 per person
$952
per person
found 7 hours ago
This is one of our favorite places to stay. Love having a kitchen and washer and dryer.

Reviewed on Apr 30, 2026

Floridays Resort Orlando
3.5-star property

Floridays Resort Orlando

8.6/10 Excellent! (11,875 reviews)

Jun 18 - Jun 23

5 night stay

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,228, price is now $1,005 per person
$1,005
per person
found 7 hours ago
Need more atention to the restrooms

Reviewed on Apr 7, 2026

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More About Flying To Lake Mary from Chicago

Route Information for Flights from Chicago to Lake Mary

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

Chicago to Lake Mary

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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.