$29 Cheap flight deals from Chicago (CHI) to The Villages (MCO)

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This Weekend's Flight Deals from Chicago to The Villages

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 - Tue, Jan 13
MDW
Midway Intl.
MCO
Orlando Intl.
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Jan 4 from Midway Intl. to Orlando Intl., returning Tue, Jan 13, priced at $197 found 6 days ago
Sun, Jan 4 - Fri, Jan 9
ORD
O'Hare Intl.
MCO
Orlando Intl.
$208 Roundtrip, found 2 hours ago
$208
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Jan 4 from O'Hare Intl. to Orlando Intl., returning Fri, Jan 9, priced at $208 found 2 hours ago
Sat, Jan 3 - Sat, Jan 10
RFD
Greater Rockford
MCO
Orlando Intl.
$479 Roundtrip, found 17 hours ago
$479
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Jan 3 from Greater Rockford to Orlando Intl., returning Sat, Jan 10, priced at $479 found 17 hours ago

Airfares from $29 One Way, $59 Round Trip from Chicago to The Villages

Prices starting at $59 for return flights and $29 for one-way flights to The Villages 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 12 - Fri, Jan 16
MDW
Chicago
MCO
Orlando
$59 Roundtrip, found 5 days ago
$59
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jan 12 from Chicago to Orlando, returning Fri, Jan 16, priced at $59 found 5 days ago
Sun, Jan 18 - Sat, Jan 24
ORD
Chicago
MCO
Orlando
$59 Roundtrip, found 18 hours ago
$59
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sun, Jan 18 from Chicago to Orlando, returning Sat, Jan 24, priced at $59 found 18 hours ago
Tue, Feb 3 - Wed, Feb 11
ORD
Chicago
MCO
Orlando
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Feb 3 from Chicago to Orlando, returning Wed, Feb 11, priced at $72 found 1 day ago
Sat, Feb 28 - Wed, Mar 4
ORD
Chicago
MCO
Orlando
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, Feb 28 from Chicago to Orlando, returning Wed, Mar 4, priced at $157 found 3 hours ago
Wed, Jan 28 - Sat, Jan 31
RFD
Rockford
MCO
Orlando
$161 Roundtrip, found 11 hours ago
$161
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Jan 28 from Rockford to Orlando, returning Sat, Jan 31, priced at $161 found 11 hours ago

The Villages economy flight packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
2.0-star property

Seasons Florida Resort

8.8/10 Excellent! (3,229 reviews)

Feb 10 - Feb 13

3 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Frontier Airlines • Coach
Price was $294, price is now $163 per person
$163
per person
found 1 day ago
Nice people. Not what I'd consider a resort. More of an updated Motel 6 from the 1970s.

Reviewed on Dec 4, 2025

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,367 reviews)

Feb 18 - Feb 22

4 night stay

Chicago (CHI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $590, price is now $293 per person
$293
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

Summerville Vacation Homes by Columbia Management
4.0-star property

Summerville Vacation Homes by Columbia Management

8.4/10 Very Good! (152 reviews)

Feb 13 - Feb 18

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $1,100, price is now $594 per person
$594
per person
found 1 day ago
This concept is nicer than staying in a hotel room. The home was spacious and decorated very well. All necessities were provided. However, the ice maker in the refrigerator was not working. We were only there for 3 nights so I didn’t bother management with it.

Reviewed on Apr 19, 2021

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The Villages packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
2.0-star property

Seasons Florida Resort

8.8/10 Excellent! (3,229 reviews)

Jan 25 - Jan 31

6 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $762, price is now $497 per person
$497
per person
found 19 hours ago
Nice people. Not what I'd consider a resort. More of an updated Motel 6 from the 1970s.

Reviewed on Dec 4, 2025

Harbor Island Beach Club by Villatel
2.0-star property

Harbor Island Beach Club by Villatel

9.4/10 Exceptional! (3 reviews)

Jan 26 - Feb 1

6 night stay

Chicago (MDW) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,462, price is now $1,614 per person
$1,614
per person
found 17 hours ago
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)

Jan 25 - Jan 31

6 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,763, price is now $1,246 per person
$1,246
per person
found 19 hours 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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The Villages first class flight packages

Price found within the past 48 hours. Click for updated prices.
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)

Jan 28 - Feb 2

5 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • FirstClass
Price was $1,986, price is now $1,511 per person
$1,511
per person
just found
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

Magic Village Views Trademark Collection by Wyndham
3.5-star property

Magic Village Views Trademark Collection by Wyndham

9/10 Wonderful! (314 reviews)

Jan 30 - Feb 6

7 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,368, price is now $1,712 per person
$1,712
per person
just found
It's not nice that you don't put enough toilet paper and then you charge us $1 per toilet paper, that's not good enough service, sorry

Reviewed on Nov 29, 2024

Evermore Orlando Resort
4.0-star property

Evermore Orlando Resort

9.6/10 Exceptional! (489 reviews)

Jan 28 - Feb 4

7 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,895, price is now $2,202 per person
$2,202
per person
just found
Amazing for families visting Orlando.

Reviewed on Oct 24, 2025

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More About Flying To The Villages from Chicago

Route Information for Flights from Chicago to The Villages

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

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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.