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Stratton economy flight packages

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Lake Bomoseen Lodge
3.5-star property

Lake Bomoseen Lodge

9.4/10 Exceptional! (985 reviews)

Oct 24 - Oct 27

3 night stay

Chicago (CHI) to Rutland (RUT)

Southwest Airlines • Roundtrip • Coach
Price was $729, price is now $539 per person
$539
per person
found 10 hours ago
We had a great stay here! This was a long weekend girls' trip. There was easy access to the lake, a clean property, and really good food on-site at the restaurant with live music. The sweet potato hummus is a must-try! The pool was refreshing with plenty of activities to choose from: cornhole, volleyball, and pickleball. There's a little ice cream shop open in the afternoon. You can take a ride on the catamaran or the tiki boat for a small fee. Our stay was reasonably priced. The staff was friendly. Just an easy, no-nonsense, enjoyable getaway. We loved it and are thinking about making this a yearly girls' trip! Thank you so much for a great stay!

Reviewed on Sep 17, 2026

My Place Hotel-Randolph VT
2.0-star property

My Place Hotel-Randolph VT

9.4/10 Exceptional! (537 reviews)

Oct 23 - Oct 30

7 night stay

Chicago (CHI) to Rutland (RUT)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,299, price is now $932 per person
$932
per person
found 4 hours ago
The hotel is clean it is rural with nothing within view a gas station and McDonald’s down the hill by the interstate. They had coffee for you in the morning but no breakfast. For the price it should include it. They had a few items and sodas , no prices and rarely anyone at the counter to ask. We did have an issue with the toilet. It moved and made a loud noise as you got up. I told the staff one morning and she stated it would be repaired when we got back that evening. It was not.

Reviewed on Sep 21, 2026

Castle Hill Resort And Spa
3.5-star property

Castle Hill Resort And Spa

9/10 Wonderful! (124 reviews)

Oct 24 - Oct 27

3 night stay

Chicago (CHI) to Rutland (RUT)

Southwest Airlines • Roundtrip • Coach
Price was $742, price is now $585 per person
$585
per person
found 10 hours ago
Th

Reviewed on Sep 19, 2026

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More About Flying To Stratton from Chicago

Route Information for Flights from Chicago to Stratton

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

Chicago to Stratton

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