$35 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.

Sat, Apr 11 - Sat, Apr 18
MDW
Midway Intl.
MCO
Orlando Intl.
$125 Roundtrip, found 4 days ago
$125
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Apr 11 from Midway Intl. to Orlando Intl., returning Sat, Apr 18, priced at $125 found 4 days ago
Sat, Apr 11 - Tue, Apr 14
ORD
O'Hare Intl.
MCO
Orlando Intl.
$243 Roundtrip, just found
$243
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 11 from O'Hare Intl. to Orlando Intl., returning Tue, Apr 14, priced at $243 just found

Airfares from $35 One Way, $69 Round Trip from Chicago to Lake Mary

Prices starting at $69 for return flights and $35 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.

Sat, May 2 - Fri, May 8
MDW
Chicago
MCO
Orlando
$69 Roundtrip, found 13 hours ago
$69
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, May 2 from Chicago to Orlando, returning Fri, May 8, priced at $69 found 13 hours ago
Thu, Apr 30 - Sat, May 9
ORD
Chicago
MCO
Orlando
$69 Roundtrip, found 12 hours ago
$69
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Chicago to Orlando, returning Sat, May 9, priced at $69 found 12 hours ago
Mon, Apr 27 - Wed, May 6
ORD
Chicago
MCO
Orlando
$87 Roundtrip, found 4 hours ago
$87
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Mon, Apr 27 from Chicago to Orlando, returning Wed, May 6, priced at $87 found 4 hours ago
Wed, May 27 - Tue, Jun 2
RFD
Rockford
MCO
Orlando
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 27 from Rockford to Orlando, returning Tue, Jun 2, priced at $169 found 1 day ago
Tue, Jun 16 - Wed, Jun 24
ORD
Chicago
MCO
Orlando
$169 Roundtrip, found 9 hours ago
$169
Roundtrip
found 9 hours ago
Select United flight, departing Tue, Jun 16 from Chicago to Orlando, returning Wed, Jun 24, priced at $169 found 9 hours ago

Lake Mary economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

8/10 Very Good! (1,836 reviews)

May 18 - May 23

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $565, price is now $245 per person
$245
per person
found 11 hours ago
Nice pools and Hot tubs. Room I had needed some updating but was a nice lay out. Could see Disney fireworks from slider!

Reviewed on Feb 16, 2026

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

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (6,071 reviews)

May 30 - Jun 6

7 night stay

Chicago (CHI) to Orlando (MCO)

Southwest Airlines • Coach

Orlando (MCO) to Chicago (CHI)

American Airlines • Coach
Price was $1,039, price is now $453 per person
$453
per person
found 1 day ago
We had to get 4 room keys for our door to finally work, however staff was kind and helped us as much as they could.

Reviewed on Feb 12, 2026

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

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

May 30 - Jun 6

7 night stay

Chicago (CHI) to Orlando (MCO)

Southwest Airlines • Coach

Orlando (MCO) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
Price was $876, price is now $400 per person
$400
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

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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.