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Chester Flights as Low as $96

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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 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 15 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 $96, 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 $96 right now, why wait?

Last Minute Hotel Deals in Chester

SpringHill Suites Chester
SpringHill Suites Chester
2.5 out of 5
12301 REDWATER CREEK ROAD, Chester, VA
The price is $135 per night from May 29 to May 30
$135
includes taxes & fees
May 29 - May 30
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (571 reviews)
"Very clean and comfortable!"

Reviewed on May 4, 2025

SpringHill Suites 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
The price is $108 per night from May 18 to May 19
$108
includes taxes & fees
May 18 - May 19
Stay at this 3-star business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,000 reviews)
"Cleanliness needs improving."

Reviewed on May 4, 2025

Country Inn & Suites by Radisson, Chester, VA
Hyatt Place Richmond/Chester
Hyatt Place Richmond/Chester
3 out of 5
13148 Kingston Ave, Chester, VA
The price is $162 per night from May 10 to May 11
$162
includes taxes & fees
May 10 - May 11
Stay at this 3-star business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (1,000 reviews)
"The hotel was under renovation so the menu was limited and only beer and wine Hopefully they will be updated if we return in the spring next year."

Reviewed on May 3, 2025

Hyatt Place Richmond/Chester
Fairfield Inn By Marriott Richmond Chester
Fairfield Inn By Marriott Richmond Chester
2.5 out of 5
12400 Redwater Creek Rd, Chester, VA
The price is $116 per night from May 18 to May 19
$116
includes taxes & fees
May 18 - May 19
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! (763 reviews)
South side of rt Richmond
"A great place to stay in the area, a lot nicer than others that cost more. Parking lot didn't feel as safe but nothing else other than yelling out from the other side of the fence. Buzzards are getting into the dumpster area and the trash of collector drops two bags of trash and doesn't hop out the ..."

Reviewed on May 6, 2025

Fairfield Inn By Marriott Richmond Chester
Comfort Inn Chester - Richmond South
Comfort Inn Chester - Richmond South
2.5 out of 5
2100 W Hundred Rd, Chester, VA
The price is $83 per night from May 18 to May 19
$83
includes taxes & fees
May 18 - May 19
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! (999 reviews)
"Overall a pleasant stay"

Reviewed on May 4, 2025

Comfort Inn Chester - Richmond South
Suburban Studios Chester
Suburban Studios Chester
2 out of 5
2403 W Hundred Rd, Chester, VA
The price is $76 per night from May 14 to May 15
$76
includes taxes & fees
May 14 - May 15
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! (335 reviews)
"Good"

Reviewed on May 3, 2025

Suburban Studios Chester
Red Roof Inn Chester
Red Roof Inn Chester
2 out of 5
2405 W Hundred Rd, Chester, VA
The price is $91 per night from May 11 to May 12
$91
includes taxes & fees
May 11 - May 12
Stay at this hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
7/10 Good! (733 reviews)
"Nice staff, clean-besides someone’s clothes being left in the dresser before we rented the room."

Reviewed on Apr 22, 2025

Red Roof Inn Chester
Omni Richmond Hotel
Omni Richmond Hotel
4 out of 5
100 S 12th St, Richmond, VA
The price is $185 per night from May 26 to May 27
$185
includes taxes & fees
May 26 - May 27
Stay at this 4-star business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful ...
8.8/10 Excellent! (1,131 reviews)
"Great service"

Reviewed on May 4, 2025

Omni Richmond 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.