Search Cheap Flights to
Chester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chester Flights as Low as $147

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

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

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 16 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 $147, 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 $147 right now, why wait?

Chester Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$146

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! (2,673 reviews)
.

Reviewed on May 14, 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! (2,010 reviews)
We always love our stay at Mohegan Sun!

Reviewed on May 11, 2026

Mohegan Sun
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! (1,000 reviews)
good

Reviewed on May 11, 2026

Red Roof Inn Meriden
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! (1,908 reviews)
everything good

Reviewed on May 15, 2026

Microtel Inn & Suites by Wyndham 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. ...
7.2/10 Good! (1,002 reviews)
Very sketchy area, staff was ok, A/C worked.

Reviewed on May 15, 2026

Motel 6 New Haven - Branford, CT
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! (1,015 reviews)
Great

Reviewed on May 9, 2026

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
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 ...
7.6/10 Good! (1,017 reviews)
Front lobby has been remodeled but that is all. Hotel is disgusting, dirty, mold, curtains are filthy and stained. Lamp shade was even filthy. I don’t think the floors have been vacuumed or moped in years. I wouldn’t eat breakfast from this hotel bc it’s so dirty. I instantly had allergy and asthma ...

Reviewed on May 12, 2026

Clarion Inn North Haven - New Haven North
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! (592 reviews)
The staff made the experience very enjoyable

Reviewed on May 14, 2026

Inn at Middletown
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.