$55 Cheap flight deals from Chicago (CHI) to Tavares (ORL)
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This Weekend's Flight Deals from Chicago to Tavares
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.
RFD
Greater Rockford
SFB
Orlando Sanford Intl.
$205 Roundtrip, found 4 days ago
$205
Roundtrip
found 4 days ago
ORD
O'Hare Intl.
MCO
Orlando Intl.
$277 Roundtrip, just found
$277
Roundtrip
just found
MDW
Midway Intl.
MCO
Orlando Intl.
$405 Roundtrip, found 3 hours ago
$405
Roundtrip
found 3 hours ago
RFD
Greater Rockford
MCO
Orlando Intl.
$546 Roundtrip, found 4 hours ago
$546
Roundtrip
found 4 hours ago
Airfares from $55 One Way, $97 Round Trip from Chicago to Tavares
Prices starting at $97 for return flights and $55 for one-way flights to Tavares were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
RFD
Rockford
SFB
Orlando
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
ORD
Chicago
MCO
Orlando
$130 Roundtrip, found 1 hour ago
$130
Roundtrip
found 1 hour ago
MDW
Chicago
MCO
Orlando
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
MDW
Chicago
MCO
Orlando
$239 Roundtrip, found 4 days ago
$239
Roundtrip
found 4 days ago
ORD
Chicago
MCO
Orlando
$271 Roundtrip, found 2 days ago
$271
Roundtrip
found 2 days ago
Tavares economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.0-star property
Seasons Florida Resort
9/10 Wonderful! (3,855 reviews)
Nov 5 - Nov 9
4 night stay
Chicago (CHI) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Price was $587, price is now $327 per person
$327
per person
found 1 day ago
Staff was amazing I called a day before to see if I could get an early check in they were more than willing to accommodate me at no charge and were super friendly and helpful.
Reviewed on Sep 20, 2026
4.0-star property
Westgate Lakes Resort & Spa Universal Studios Area
8.4/10 Very Good! (7,020 reviews)
Nov 5 - Nov 9
4 night stay
Chicago (CHI) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $831, price is now $462 per person
$462
per person
found 1 day ago
Staff was nice. Room was clean and shuttles on property made getting around easy.
Reviewed on Sep 20, 2026
Tavares packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Westgate Lakes Resort & Spa Universal Studios Area
8.4/10 Very Good! (7,020 reviews)
Nov 2 - Nov 6
4 night stay
Chicago (ORD) to Orlando (MCO)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $830, price is now $591 per person
$591
per person
found 18 hours ago
Staff was nice. Room was clean and shuttles on property made getting around easy.
Reviewed on Sep 20, 2026
Tavares business class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Bayfront Westcott House St Augustine B&B
9.8/10 Exceptional! (321 reviews)
Nov 1 - Nov 4
3 night stay
Chicago (ORD) to Orlando (MCO)
Frontier Airlines • Roundtrip • BusinessClass
Price was $1,002, price is now $842 per person
$842
per person
found 1 day ago
We took a spur of the moment trip to St.Augustine and by some miracle there was a room available at Bayfront Westcott. We were met by Sandy the manager who helped us get sorted out. It was happy hour and we met some other people who were staying and everyone was having a great time in the quaint but beautiful dining room.
Our room was beautiful and had everything we needed and was exactly what we needed. Our breakfast the next morning was delicious and we highly recommend staying there!
Reviewed on Sep 12, 2026
3.5-star property
The Kenwood Inn
9.6/10 Exceptional! (400 reviews)
Nov 1 - Nov 4
3 night stay
Chicago (ORD) to Orlando (MCO)
Frontier Airlines • Roundtrip • BusinessClass
Price was $1,093, price is now $918 per person
$918
per person
found 1 day ago
Wonderful hotel with very helpful staff and an incredible breakfast! Highly recommend and would definitely return.
Reviewed on Sep 18, 2026
3.5-star property
Casablanca Inn on the Bay
8.8/10 Excellent! (1,003 reviews)
Nov 1 - Nov 4
3 night stay
Chicago (ORD) to Orlando (MCO)
Frontier Airlines • Roundtrip • BusinessClass
Price was $1,252, price is now $1,063 per person
$1,063
per person
found 1 day ago
The location is everything about this stay. They had free coffee in the main hotel area. Rooms were looking nice for as old as this place is. I was in room 17 that looks onto a city view as they called it but it was other homes. This inn allows pets and my neighbor had a dog that was barking all evening. The room had very nice linen on the bed but the bed was not comfortable at all and the pillows did not provide any support. I guess the central air and heating was broken because all that our room had was a small window unit which meant the bathroom always stayed hot because there was no air circulating through there. but it was all worth the hassle just for the location and proximity to all the downtown historical area.
Reviewed on Sep 18, 2026
Tavares first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Carriage Way Inn
9.8/10 Exceptional! (873 reviews)
Nov 1 - Nov 5
4 night stay
Chicago (ORD) to Orlando (MCO)
United • FirstClass
Orlando (MCO) to Chicago (ORD)
Delta • FirstClass
Price was $1,581, price is now $1,405 per person
$1,405
per person
found 1 day ago
Loved it
Reviewed on Sep 12, 2026
3.5-star property
The Kenwood Inn
9.6/10 Exceptional! (400 reviews)
Nov 1 - Nov 5
4 night stay
Chicago (ORD) to Orlando (MCO)
United • FirstClass
Orlando (MCO) to Chicago (ORD)
Delta • FirstClass
Price was $1,632, price is now $1,408 per person
$1,408
per person
found 1 day ago
Wonderful hotel with very helpful staff and an incredible breakfast! Highly recommend and would definitely return.
Reviewed on Sep 18, 2026
3.5-star property
Casablanca Inn on the Bay
8.8/10 Excellent! (1,003 reviews)
Nov 1 - Nov 5
4 night stay
Chicago (ORD) to Orlando (MCO)
United • FirstClass
Orlando (MCO) to Chicago (ORD)
Delta • FirstClass
Price was $1,850, price is now $1,604 per person
$1,604
per person
found 1 day ago
The location is everything about this stay. They had free coffee in the main hotel area. Rooms were looking nice for as old as this place is. I was in room 17 that looks onto a city view as they called it but it was other homes. This inn allows pets and my neighbor had a dog that was barking all evening. The room had very nice linen on the bed but the bed was not comfortable at all and the pillows did not provide any support. I guess the central air and heating was broken because all that our room had was a small window unit which meant the bathroom always stayed hot because there was no air circulating through there. but it was all worth the hassle just for the location and proximity to all the downtown historical area.
Reviewed on Sep 18, 2026
More About Flying To Tavares from Chicago
Route Information for Flights from Chicago to Tavares
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | ORL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Tavares
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Cruising for a bargain deal
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Cheap Chicago to Tavares flights that lead to rewards
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Quality combinations
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Tavares Airports
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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.