$30 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, Jan 4 - Sun, Jan 11
MDW
Midway Intl.
MCO
Orlando Intl.
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jan 4 from Midway Intl. to Orlando Intl., returning Sun, Jan 11, priced at $261 found 1 day ago
Sun, Jan 4 - Tue, Feb 3
ORD
O'Hare Intl.
MCO
Orlando Intl.
$306 Roundtrip, just found
$306
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Jan 4 from O'Hare Intl. to Orlando Intl., returning Tue, Feb 3, priced at $306 just found
Sat, Jan 3 - Sat, Jan 10
RFD
Greater Rockford
MCO
Orlando Intl.
$479 Roundtrip, found 4 days ago
$479
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jan 3 from Greater Rockford to Orlando Intl., returning Sat, Jan 10, priced at $479 found 4 days ago

Airfares from $30 One Way, $58 Round Trip from Chicago to Lake Mary

Prices starting at $58 for return flights and $30 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.

Mon, Jan 26 - Thu, Feb 5
MDW
Chicago
MCO
Orlando
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jan 26 from Chicago to Orlando, returning Thu, Feb 5, priced at $58 found 1 day ago
Mon, Jan 26 - Thu, Jan 29
ORD
Chicago
MCO
Orlando
$59 Roundtrip, found 1 hour ago
$59
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Jan 26 from Chicago to Orlando, returning Thu, Jan 29, priced at $59 found 1 hour ago
Tue, Jan 20 - Fri, Jan 23
ORD
Chicago
MCO
Orlando
$71 Roundtrip, found 2 hours ago
$71
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Jan 20 from Chicago to Orlando, returning Fri, Jan 23, priced at $71 found 2 hours ago
Wed, Feb 18 - Tue, Feb 24
ORD
Chicago
MCO
Orlando
$159 Roundtrip, just found
$159
Roundtrip
just found
Select United flight, departing Wed, Feb 18 from Chicago to Orlando, returning Tue, Feb 24, priced at $159 just found
Tue, Feb 3 - Sat, Feb 7
ORD
Chicago
MCO
Orlando
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Feb 3 from Chicago to Orlando, returning Sat, Feb 7, priced at $159 found 1 hour ago

Lake Mary economy flight packages

Price found within the past 48 hours. Click for updated prices.
CoCo Key Hotel and Water Resort 
3.5-star property

CoCo Key Hotel and Water Resort 

8/10 Very Good! (3,666 reviews)

Feb 7 - Feb 14

7 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $623, price is now $279 per person
$279
per person
found 1 day ago
My wife didn't really care for the place! Pool area was the best part about this place.

Reviewed on Dec 2, 2025

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

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,482 reviews)

Feb 7 - Feb 14

7 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $891, price is now $385 per person
$385
per person
found 1 day ago
It was ok for the price

Reviewed on Sep 27, 2025

I-Drive Hotel at Universal
2.5-star property

I-Drive Hotel at Universal

6.8/10 (1,002 reviews)

Feb 15 - Feb 20

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $767, price is now $387 per person
$387
per person
found 1 day ago
Honestly, great staff, room was nice, location was right there on idrive. I could leave my car in the parking lot and walk down idrive to all the places I wanted to go. I give them only 3 stars because I reserved a King suite and upon arrival I was given a different room and told no kings available despite previous interactions and arriving early. The bathroom aesthetics weren’t there. Super basic, worn n rusted, and my first time stepping into the restroom after getting my room keys, I found several wet towels hanging as if someone recently used the shower and the room wasn’t clean. I had to go into detective mode and inspect everything and bed sheets.

Reviewed on Nov 26, 2025

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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

8.2/10 Very Good! (5,482 reviews)

Feb 3 - Feb 6

3 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $683, price is now $502 per person
$502
per person
found 1 day ago
It was ok for the price

Reviewed on Sep 27, 2025

Florida Hotel & Conference Center in the Florida Mall
3.5-star property

Florida Hotel & Conference Center in the Florida Mall

9.2/10 Wonderful! (2,232 reviews)

Feb 3 - Feb 6

3 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $875, price is now $668 per person
$668
per person
found 1 day ago
What a stunning and beautiful hotel. My son loved it also and having full access to the mall was a bonus!! Will definitely be back soon!

Reviewed on Dec 9, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays
4.0-star property

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9.2/10 Wonderful! (1,001 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,496, price is now $1,175 per person
$1,175
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

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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.