Cheap flight deals from Chicago (CHI) to Brattleboro (VSF)

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Brattleboro economy flight packages

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Lincoln Inn & Gallery
3.0-star property

Lincoln Inn & Gallery

8.6/10 Excellent! (67 reviews)

Jul 4 - Jul 6

2 night stay

Chicago (CHI) to Springfield (VSF)

United • Non-stop • Coach

Springfield (VSF) to Chicago (CHI)

Cape Air • Non-stop • Coach
Price was $723, price is now $655 per person
$655
per person
found 1 day ago
Exceeded our expectations! Cozy, warm, clean vintage room. Easy in front parking, and super friendly and helpful staff. Beautiful views all around the property. Quiet and safe. Proximity perfect to everything in the area, from skiing resort to restaurants, bridges, farmer's markets, and parks. The staff will go above and beyond to make your stay enjoyable and hassle-free. After our car broke down, we were stuck without any way to get to the rental car lot. There is no Uber in the area. The owner of the hotel did not hesitate to help us and drove us to NH, an almost one-hour drive, to pick up a rental car. The owners were also helpful in recommending local restaurants and local activities.

Reviewed on Feb 9, 2026

The Vesper
3.0-star property

The Vesper

9.4/10 Exceptional! (60 reviews)

Jul 4 - Jul 6

2 night stay

Chicago (CHI) to Springfield (VSF)

United • Non-stop • Coach

Springfield (VSF) to Chicago (CHI)

Cape Air • Non-stop • Coach
Price was $825, price is now $769 per person
$769
per person
found 1 day ago
Loved my stay. It was so quiet and comfortable. The town of Woodstock is adorable.

Reviewed on Apr 5, 2026

Woodstock Inn & Resort
4.5-star property

Woodstock Inn & Resort

9.4/10 Exceptional! (576 reviews)

Jul 4 - Jul 6

2 night stay

Chicago (CHI) to Springfield (VSF)

United • Non-stop • Coach

Springfield (VSF) to Chicago (CHI)

Cape Air • Non-stop • Coach
Price was $1,231, price is now $1,158 per person
$1,158
per person
found 1 day ago
The Hotel is nice but the staff are not very well trained at the front desk. Our room was not ready at 4! The price of the room is outlandish compared to what you are getting.

Reviewed on Dec 23, 2024

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More About Flying To Brattleboro from Chicago

Route Information for Flights from Chicago to Brattleboro

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

Chicago to Brattleboro

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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.