Cheap flight deals from Chicago (CHI) to Silver Springs (OCF)

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Silver Springs economy flight packages

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

Seasons Florida Resort

9/10 Wonderful! (3,462 reviews)

May 18 - May 23

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $426, price is now $218 per person
$218
per person
found 1 day ago
I rated 5-stars for the location and price of the stay. The rooms were in fact clean, but perhaps the age of the hotel (even though renovated) had a particular smell that only helped when running the a/c which wasn’t needed (I visited during the January attic blast).

Reviewed on Feb 10, 2026

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

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

May 18 - May 23

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $583, price is now $229 per person
$229
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 Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,233 reviews)

May 20 - May 23

3 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $611, price is now $301 per person
$301
per person
found 1 day ago
Great location had a good time

Reviewed on Dec 28, 2025

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Silver Springs packages with premium economy flights

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Comfort Inn Kissimmee-Lake Buena Vista South
3.0-star property

Comfort Inn Kissimmee-Lake Buena Vista South

7.4/10 Good! (1,003 reviews)

May 26 - May 29

3 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $415, price is now $354 per person
$354
per person
found 1 day ago
Room wasna lil dirty but everythingnelse good

Reviewed on Feb 1, 2026

Encore Resort and Water Park at Reunion by Rentyl
5.0-star property

Encore Resort and Water Park at Reunion by Rentyl

8.2/10 Very Good! (1,007 reviews)

May 26 - May 29

3 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,010, price is now $854 per person
$854
per person
found 1 day ago
Very nice property! Convenient to grocery shopping and Disney attractions. Customer service was very helpful. Bartender at pool attitude was not pleasant and drinks were weak along with prices too high for the service. Overall great service!

Reviewed on Jun 22, 2024

Orlando Vacation Rooms
3.0-star property

Orlando Vacation Rooms

8.2/10 Very Good! (178 reviews)

May 26 - May 29

3 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $394, price is now $355 per person
$355
per person
found 1 day ago
I think for the money, this place is great. It appears to have been remodeled very cleanly and simply. The check in was quick and easy. Room was nice and clean. Bed was nice and AC was perfect. The shower was good. I was able to walk to Macaroni Grill for dinner, which was nice after a 7 hour drive. I had my choice of 4 or 5 restaurants I could have walked to, which was nice. Only 10 miles to Mecum car auction. Easy out this morning. I will be back in 2025.

Reviewed on Jan 14, 2024

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Silver Springs first class flight packages

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Vero Beach Inn & Suites I-95
3.0-star property

Vero Beach Inn & Suites I-95

8.6/10 Excellent! (1,524 reviews)

Jun 2 - Jun 7

5 night stay

Rockford (RFD) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,408, price is now $1,249 per person
$1,249
per person
found 1 day ago
A few things in the room didn’t work: TV, safe and bedside lamp (room 221).

Reviewed on Jan 10, 2026

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More About Flying To Silver Springs from Chicago

Route Information for Flights from Chicago to Silver Springs

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

Chicago to Silver Springs

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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.

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