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Chester

Chester Flights as Low as $206

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$206 Roundtrip, found 6 hours ago
$206
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $206 found 6 hours ago
Breeze Airways
Thu, Dec 3 - Thu, Dec 3
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Dec 3, priced at $207 found 1 day ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$211 Roundtrip, found 6 hours ago
$211
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $211 found 6 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$216 Roundtrip, found 6 hours ago
$216
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $216 found 6 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$222 Roundtrip, found 6 hours ago
$222
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $222 found 6 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$227 Roundtrip, found 6 hours ago
$227
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $227 found 6 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$232 Roundtrip, found 6 hours ago
$232
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $232 found 6 hours ago
Breeze Airways
Fri, Oct 16 - Mon, Oct 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$237 Roundtrip, found 9 hours ago
$237
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Oct 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Oct 19, priced at $237 found 9 hours ago
Breeze Airways
Fri, Oct 16 - Mon, Oct 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$242 Roundtrip, found 9 hours ago
$242
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Oct 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Oct 19, priced at $242 found 9 hours ago
Breeze Airways
Fri, Oct 16 - Mon, Oct 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$247 Roundtrip, found 9 hours ago
$247
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Oct 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Oct 19, priced at $247 found 9 hours ago
Breeze Airways
Thu, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$252 Roundtrip, found 1 day ago
$252
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Oct 22 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Nov 8, priced at $252 found 1 day ago
Breeze Airways
Mon, Sep 28 - Mon, Sep 28
JAX
Jacksonville Intl.
HVN
Tweed - New Haven Regional
$283 Roundtrip, found 2 days ago
$283
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Sep 28 from Jacksonville Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at $283 found 2 days ago
Avelo Airlines
Fri, Oct 16 - Mon, Oct 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$285 Roundtrip, found 9 hours ago
$285
Roundtrip
found 9 hours ago
Select Avelo Airlines flight, departing Fri, Oct 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Oct 19, priced at $285 found 9 hours ago
Avelo Airlines
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$286 Roundtrip, found 6 hours ago
$286
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $286 found 6 hours ago
Breeze Airways
Mon, Sep 28 - Mon, Sep 28
JAX
Jacksonville Intl.
HVN
Tweed - New Haven Regional
$294 Roundtrip, found 2 days ago
$294
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Sep 28 from Jacksonville Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at $294 found 2 days ago
Avelo Airlines
Sat, Oct 10 - Thu, Oct 15
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$363 Roundtrip, found 5 days ago
$363
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Sat, Oct 10 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Oct 15, priced at $363 found 5 days ago

Last Minute Hotel Deals in Chester

Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

2.5 out of 5
269 North Frontage Road New London CT
Book a stay at this family-friendly hotel in New London. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6/10 (1,005 reviews)
"This hotel is a good bargain. Although worn down in general, it suited our needs for one night. Very comfortable bed, quiet, and good buffet breakfast. Near shopping and the highway so convenient too."

Reviewed on Sep 25, 2026

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Regency Inn & Suites New London, Mystic
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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Pier Blue Inn Old Saybrook - Essex
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Book a stay at this business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,769 reviews)
"Room was very clean and staff was friendly and helpful. No shuttle service to the casino weekdays. The complimentary breakfast was OK ... not a lot of choices. While I didn't expect real table ware, the low quality paper plates and utensils were a negative. Average quality paper plates and utensils ..."

Reviewed on Sep 25, 2026

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Hyatt Place Uncasville - Casino Area
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (1,022 reviews)
"Great experience again enjoy the location and quiet"

Reviewed on Sep 25, 2026

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Motel 6 New Haven - Branford, CT
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
1954 Norwich New London Tpke Montville CT
Book a stay at this business-friendly hotel in Montville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the breakfast and the ...
8.6/10 Excellent! (2,076 reviews)
"People very helpful. Good breakfast. Close to a lot of activity"

Reviewed on Sep 24, 2026

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Microtel Inn & Suites by Wyndham Uncasville Casino Area
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
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Water's Edge Resort & Spa
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Book a stay at this business-friendly hotel in Meriden. Enjoy free WiFi, free parking, and a health club. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (1,004 reviews)
"No comments"

Reviewed on Sep 26, 2026

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Red Roof Inn Meriden
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
201 Washington Avenue North Haven CT
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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Clarion Inn North Haven - New Haven North
See all 1,108 properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.