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Chester

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Chester Flights as Low as $130

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

Breeze Airways
Breeze Airways
Breeze Airways
Avelo Airlines
Breeze Airways
Breeze Airways
Avelo Airlines

Cheap Flights to Chester

Fall in love at first flight with your vacation to Chester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the FID airport.

What is the cheapest month to fly to Chester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chester are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 7 to choose from for your flight to Chester.

What airport is best to fly into Chester?

When you’re planning your trip to Chester, convenience is the name of the game. Luckily, Chester Tweed - New Haven Regional Airport is nearby so you can deplane and get going on checking off everything on your Chester must-do list.

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $130, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chester?

The trick to saving a stack of cash on your flight to Chester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $130 right now, why wait?

Chester Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$107

Last Minute Hotel Deals in Chester

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 ...
9.2/10 Wonderful! (2,678 reviews)
Breakfast was a buffet. The eggs were watered down a little bit too much but everything else satisfactory. Parking was seemed safe with plenty of spaces!

Reviewed on Apr 30, 2026

Hyatt Place Uncasville - Casino Area
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
Book a stay at this luxury resort in Montville. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (2,020 reviews)
We had an amazing stay! I would recommend this hotel to anyone who is looking for a little get away.

Reviewed on Apr 27, 2026

Mohegan Sun
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 WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,888 reviews)
Check i was excellent as i was a little early and the front desk let me check in early.Then i locked myself out of the room on which he canceled the first 2 keys and reissued 2 more .He was very understanding and helpful. Room was clean.Only thing i would have preferred a fridge and a microwave,but ...

Reviewed on Apr 27, 2026

Microtel Inn & Suites by Wyndham Uncasville Casino Area
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 ...
7.4/10 Good! (1,001 reviews)
The hotel was actually pretty clean, however the room smelled of old nicotine smoke or something, I asked to be moved to another room and they did so right away, but it smelled the same. The place in general really needs to be updated with new carpeting etc. The price for the room was low, I guess ...

Reviewed on May 1, 2026

Red Roof Inn Meriden
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

3 out of 5
2255 Norwich-New London Turnpike 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 ...
9.2/10 Wonderful! (1,000 reviews)
I disliked the shower head pressure!

Reviewed on May 1, 2026

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
Inn at Middletown

Inn at Middletown

3.5 out of 5
70 Main Street Middletown CT
Book a stay at this business-friendly hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
9/10 Wonderful! (576 reviews)
Convenient, charming

Reviewed on Apr 24, 2026

Inn at Middletown
The Spa at Norwich Inn

The Spa at Norwich Inn

3.5 out of 5
607 W Thames St Norwich CT
Book a stay at this spa hotel in Norwich. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,001 reviews)
We just loved our time at the spa and the hotel. The restaurant and pub were great!! The breakfast was divine. The wait staff in restaurants and the spa people were wonderful- so friendly, fun and helpful!!

Reviewed on Apr 28, 2026

The Spa at Norwich Inn
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. ...
7.2/10 Good! (1,000 reviews)
The room smelled terrible. It was a typical Motel 6 with a hard bed and unusual guests.

Reviewed on Apr 25, 2026

Motel 6 New Haven - Branford, CT
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.