$37 Cheap flight deals from Chicago (CHI) to Eustis (ORL)

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This Weekend's Flight Deals from Chicago to Eustis

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, Feb 1 - Wed, Feb 11
ORD
O'Hare Intl.
MCO
Orlando Intl.
$125 Roundtrip, found 2 hours ago
$125
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Feb 1 from O'Hare Intl. to Orlando Intl., returning Wed, Feb 11, priced at $125 found 2 hours ago
Sun, Feb 1 - Thu, Feb 5
MDW
Midway Intl.
MCO
Orlando Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Feb 1 from Midway Intl. to Orlando Intl., returning Thu, Feb 5, priced at $137 found 1 day ago
Sun, Feb 1 - Mon, Feb 2
RFD
Greater Rockford
MCO
Orlando Intl.
$304 Roundtrip, found 4 days ago
$304
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Feb 1 from Greater Rockford to Orlando Intl., returning Mon, Feb 2, priced at $304 found 4 days ago

Airfares from $37 One Way, $74 Round Trip from Chicago to Eustis

Prices starting at $74 for return flights and $37 for one-way flights to Eustis 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, Feb 28 - Wed, Mar 4
ORD
Chicago
MCO
Orlando
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Feb 28 from Chicago to Orlando, returning Wed, Mar 4, priced at $74 just found
Sun, Feb 8 - Sat, Feb 28
MDW
Chicago
MCO
Orlando
$91 Roundtrip, found 3 days ago
$91
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Feb 8 from Chicago to Orlando, returning Sat, Feb 28, priced at $91 found 3 days ago
Sat, Feb 21 - Tue, Feb 24
RFD
Rockford
MCO
Orlando
$161 Roundtrip, found 6 days ago
$161
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Feb 21 from Rockford to Orlando, returning Tue, Feb 24, priced at $161 found 6 days ago
Fri, Feb 27 - Wed, Mar 4
ORD
Chicago
MCO
Orlando
$180 Roundtrip, found 7 hours ago
$180
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Fri, Feb 27 from Chicago to Orlando, returning Wed, Mar 4, priced at $180 found 7 hours ago
Wed, Feb 18 - Sat, Feb 28
ORD
Chicago
MCO
Orlando
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Feb 18 from Chicago to Orlando, returning Sat, Feb 28, priced at $197 found 5 days ago

Eustis economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort
3.5-star property

Westgate Towers Resort

8.6/10 Excellent! (1,002 reviews)

Feb 28 - Mar 4

4 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $465, price is now $212 per person
$212
per person
found 1 day ago
Great place and very clean. They provide so many amenities

Reviewed on Aug 24, 2025

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

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

Mar 1 - Mar 8

7 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $912, price is now $398 per person
$398
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

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)

Mar 1 - Mar 8

7 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $1,064, price is now $484 per person
$484
per person
found 1 day ago
It was ok for the price

Reviewed on Sep 27, 2025

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Eustis packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0-star property

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

7.8/10 Good! (188 reviews)

Mar 8 - Mar 11

3 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $738, price is now $555 per person
$555
per person
found 1 day ago
The staff were amazing, the parking for the hotel was horrible.

Reviewed on Jan 3, 2026

Westgate Blue Tree Resort in Lake Buena Vista
3.5-star property

Westgate Blue Tree Resort in Lake Buena Vista

8.4/10 Very Good! (1,002 reviews)

Mar 8 - Mar 11

3 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $762, price is now $567 per person
$567
per person
found 1 day ago
The place is very nice! However, the washer did not work.

Reviewed on Oct 31, 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)

Mar 8 - Mar 11

3 night stay

Chicago (CHI) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,225, price is now $920 per person
$920
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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Eustis first class flight packages

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

Mar 13 - Mar 17

4 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (CHI)

Delta • FirstClass
Price was $1,299, price is now $1,050 per person
$1,050
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

Evermore Orlando Resort
4.0-star property

Evermore Orlando Resort

9.6/10 Exceptional! (489 reviews)

Mar 13 - Mar 17

4 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (CHI)

Delta • FirstClass
Price was $2,672, price is now $2,147 per person
$2,147
per person
found 1 day ago
Amazing for families visting Orlando.

Reviewed on Oct 24, 2025

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,002 reviews)

Mar 13 - Mar 17

4 night stay

Chicago (CHI) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Chicago (CHI)

Delta • FirstClass
Price was $1,256, price is now $1,061 per person
$1,061
per person
found 1 day ago
Great location for hospital access

Reviewed on Jul 8, 2025

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More About Flying To Eustis from Chicago

Route Information for Flights from Chicago to Eustis

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

Chicago to Eustis

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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.