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 $100

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

Spirit Airlines
Spirit Airlines
Breeze Airways
Spirit Airlines
Spirit Airlines
Breeze Airways
Bargain Flight
Bargain Flight
Bargain Flight
Frontier Airlines
Frontier Airlines
Frontier Airlines
JetBlue Airways
Spirit Airlines
American Airlines
American 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 RIC 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 April, 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 13 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 Richmond Intl. 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 $100, 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 $100 right now, why wait?

Chester Flight Information
Destination airport
Richmond Intl.
Destination airport IATA code
RIC
Roundtrip price
$100

Last Minute Hotel Deals in Chester

Suburban Studios Chester

Suburban Studios Chester

2 out of 5
2403 W Hundred Rd Chester VA
Book a stay at this business-friendly hotel in Chester. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Parker's Battery Park and The ...
8/10 Very Good! (508 reviews)
Great place rooms exactly as pictured and no nonsense staff which is amazing for traveling business partners!!

Reviewed on Mar 18, 2026

Suburban Studios Chester
Country Inn & Suites by Radisson, Chester, VA

Country Inn & Suites by Radisson, Chester, VA

3 out of 5
2406 W Hundred Rd Chester VA
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (1,001 reviews)
Very little interaction with the staff

Reviewed on Mar 17, 2026

Country Inn & Suites by Radisson, Chester, VA
Fairfield Inn By Marriott Richmond Chester

Fairfield Inn By Marriott Richmond Chester

3 out of 5
12400 Redwater Creek Rd Chester VA
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in our ...
8.2/10 Very Good! (905 reviews)
They didn't clean my rooms and I had a tick bite on my left arm

Reviewed on Mar 18, 2026

Fairfield Inn By Marriott Richmond Chester
Candlewood Suites Chester Richmond by IHG

Candlewood Suites Chester Richmond by IHG

2.5 out of 5
225 E Hundred Rd Chester VA
Stay at this hotel in Chester. Enjoy parking (surcharge), a 24-hour front desk, and air conditioning. Popular attractions Point of Rocks Park and Henricus Historical ...
9.2/10 Wonderful! (94 reviews)
Everything was nice. The bed was my only issue. Ive slept in way cheaper hotels with way better beds. This was like sleeping on the floor.

Reviewed on Mar 11, 2026

Candlewood Suites Chester Richmond by IHG
Hampton Inn by Hilton Chester South

Hampton Inn by Hilton Chester South

2.5 out of 5
12610 Chestnut Hill Rd Chester VA
Stay at this hotel in Chester. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
8/10 Very Good! (723 reviews)
Carpet in the room was terribly dirty, ripped, worn and stained. Room was very musty smelling. Bed was not well made.

Reviewed on Mar 13, 2026

Hampton Inn by Hilton Chester South
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St Richmond VA
Book a stay at this business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful ...
9/10 Wonderful! (1,342 reviews)
We were rather disappointed with our on-night stay, to be honest. We were expecting more from staying at an Omni Hotel. The room had a bad smell from the carpeting. The mattress sagged, and the bedding was only a thin woven blanket between flat sheets, not unlike the kind you get at the ER. The bathtub ...

Reviewed on Mar 18, 2026

Omni Richmond Hotel
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
301 West Franklin Street Richmond VA
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and ...
8.4/10 Very Good! (1,352 reviews)
Room was clean. Staff was very helpful.

Reviewed on Mar 19, 2026

Graduate by Hilton Richmond
The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street Richmond VA
Book a stay at this luxury hotel in Richmond. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the comfy rooms in ...
9.8/10 Exceptional! (1,005 reviews)
Room was clean.

Reviewed on Mar 18, 2026

The Jefferson Hotel
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.