Chester Holidays from £892
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Your Chester Holiday
With a Chester holiday package, say goodbye to endless planning and hello to an effortless adventure. Every detail of your escape has been taken care of before you depart, so you can spend more time experiencing this fantastic city. A trip to Chester is a wonderful opportunity to do a bit of sightseeing. Be sure to stop by well-known attractions like Chester Skating Rink, Popeye Museum and Marys River Covered Bridge. Expedia is here to help you escape the everyday. Tailor your holiday to Chester to suit your travel style, whatever that may look like.
Top Chester Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
£903
per person
19 Nov - 22 Nov
found 1 day ago
Return direct flight included
London (LHR) to St. Louis (STL)
9.2/10 Wonderful! (1,679 reviews)
The staff are super helpful, friendly and professional. The room was very comfortable and quiet. Some of the furnishings are overdue for replacement (chairs with worn out upholstery) but nothing terrible. Overall wonderful stay and will definitely return to next time I am in this area.
Reviewed on 3 Oct 2026
The Cheshire
£942
per person
19 Nov - 22 Nov
found 1 day ago
Return direct flight included
London (LHR) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
There was different types of hair where the coffee items sit. Feel like that area should be spotless. Bed was very comfortable. A/C worked great!
Reviewed on 3 Oct 2026
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 8,600 |
Max Temp Winter | 7ºC |
Max Temp Summer | 29ºC |
Top Sights | Randolph County State Recreation Area, Chester Skating Rink and Elzie C. Segar Memorial Park |
Top hotels in Chester
Baymont by Wyndham Chester IL
2150 State Street Chester IL
Fully refundableReserve now, pay when you stay
£70
6 Oct - 7 Oct
includes taxes & fees
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
7555 State Hwy Y French Village MO
£121
1 Nov - 2 Nov
includes taxes & fees
10/10 Exceptional! (109 reviews)
"I loved everything about this cabin and I was on a high from this experience."
Reviewed on 26 Sept 2026
Holiday Inn Express & Suites Perryville by IHG
2020 Jefferson St Perryville MO
Fully refundable
£82
1 Nov - 2 Nov
includes taxes & fees
9.2/10 Wonderful! (632 reviews)
"Convenient place to stay. Being close to the highway, you do hear road noise."
Reviewed on 3 Oct 2026
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.
Stay near popular Chester attractions
Popeye Museum
9.4/10 (10 reviews)
Step into the world's only Popeye museum, showcasing rare memorabilia of the iconic sailor and his creator. Explore the Character Trail afterwards to discover whimsical statues throughout Chester.
Fort Kaskaskia
9.6/10 (4 reviews)
Explore the earthen remains of this 18th-century French fortification, once protecting Illinois' first capital. Savour panoramic Mississippi River views while discovering colonial history at the interpretive overlook.
Cohen Memorial Home
This 1855 historic residence showcases distinctive blue storm windows and overlooks the Mississippi River. Tour the upstairs bedrooms with authentic furnishings or reserve the parlours for special events by appointment.
Mary's River Covered Bridge
9.0/10 (6 reviews)
This historic 1854 covered bridge, the last of its kind in southern Illinois, showcases original white oak craftsmanship. Photographers capture its timeless charm against seasonal foliage in the peaceful countryside.
Chester Bridge
This historic 1942 structure spans the Mississippi River, connecting Illinois and Missouri with engineering elegance. Visit the nearby Welcome Centre for panoramic river views and a glimpse of Chester's Popeye heritage.
Kaskaskia Bell
10.0/10 (2 reviews)
Cast in 1741 by King Louis XV, the Liberty Bell of the West rang to celebrate America's independence in 1778. Press the button to enter the shrine and view murals depicting Kaskaskia's colonial history.
Elzie C. Segar Memorial Park
7.6/10 (4 reviews)
This riverside park honours Elzie Segar, Chester's native son who created the iconic Popeye character. Admire the 900-pound bronze Popeye statue while enjoying scenic Mississippi River views.
Randolph County State Recreation Area
9.0/10 (2 reviews)
Nestled among 1,101 acres of rolling hills, this recreation area offers serene lakeside activities and wooded trails. Reserve a campsite with electric hookups for the ultimate outdoor retreat surrounded by nature.
Frequently asked questions
How much does a Chester travel package cost?
We make it simple to travel somewhere new, with Chester packages starting from just £892. You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate escape, why not add a couple of activities and tours to your travel itinerary?
If I'm not able to travel, can I cancel my Chester travel package?
Don't worry if you're rethinking your Chester travel package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We realise life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.
How do I get a cheap travel package to Chester?
You'll save tons of cash if you combine your hotels, flights and car rentals into a Chester travel package. Sometimes cheap means fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 properties all over the world, so you'll always have plenty of options to choose from. Like to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Chester holidays?
Expedia has teamed up with online lender Klarna to make your next break easier on your budget. Paying in instalments means you can spread the costs of your next adventure, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find something that suits your budget. Check out these flexible payment options:
- Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
- Pay in instalments holidays: If you'd like to pay for your escape in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: When you come across an unbeatable deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.
Where should I stay in Chester?
With interesting attractions like Elzie C. Segar Memorial Park and Chester Skating Rink in this area, try to find a hotel situated near either of them. Popeye Museum is another Chester hot spot that visitors flock to.
What are the top hotels in Chester?
If it's your first time staying in Chester, reserve a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both offer friendly service and are favourites among many travellers.
How far in advance should I book my Chester holiday?
Smart travellers will likely want to book as early as possible. You can generally look up international fares on Expedia up to a year before your intended flight. If you're booking last minute, don't stress. Low prices occasionally occur in the last weeks prior to departure.
What does an Expedia Chester travel package include?
That depends on what you're looking for. If you're travelling solo, you might decide to combine hotels and flights. Taking the whole family to Chester? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility and freedom to tailor your travel package.
What should I know before booking a Chester travel package?
We already have low prices. However, you'll score even more savings when you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and a terrific range of choice.
Can I choose my airline with a Chester Expedia travel package?
Yes, you sure can. We offer more than 550 partner airlines globally, so opt for the carrier that's a good fit for your budget needs.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
