How to find the best hotel deal in Westchester
If booking your flights with us feels easy, just wait until you give our hotel search a try. Find top Westchester hotels at low prices with these helpful hints.
Plan ahead to save on your Westchester hotel. You'll also have a wider selection of stays and room types to choose from, particularly during high-demand times.
That said, booking at the last minute can work to your advantage. Some places cut their rates a day or two before check-in to avoid having empty rooms.
Flexible on dates? Consider it your ticket to a lower rate. Change up your travel window to discover what deals pop up. Prices are typically cheaper midweek and outside peak seasons.
Avoid surprise fees later on by searching for stays with free cancellation. If your plans change or you find a better deal, you can cancel without penalty.
Where to stay in Westchester
Central Westchester
Central Westchester is where the city comes alive. If sightseeing is on your to-do list, stay at any of these hotels and you'll find yourself near some classic attractions.
If your plan is to stay nice and close to Norfolk Park, head straight to MainStay Suites Chicago Hillside. This Westchester hotel is about 2 kilometers from this major sight.
When it comes to accommodation options close to High Ridge Park, The Hyatt Lodge at Oak Brook is hard to beat. Unpack your bags at this Westchester hotel and you'll be roughly 5 kilometers away.
Hotels near Divine Providence Catholic Church are also well worth checking out. Four Points by Sheraton Chicago Westchester/Oak Brook is 2 kilometers or so from this leading sight. It's a good base for discovering the city more broadly.
When to go to Westchester
The weather can play a big part in when you choose to travel. If you prefer warmer conditions, July typically delivers with temperatures that reach a high of 29ºC (84ºF).
January is the coolest month, with lows of -13ºC (9ºF).
Want to visit when you're less likely to need an umbrella? Search for Westchester hotels in November. It's the driest time to visit, with five days of rain on average.
The wettest time of year is January. Travel then and you can expect to get around nine days of rainfall.
Best hotels in Westchester
Best budget hotels
Stretch your money further by choosing from around 90 budget Westchester hotels. Perfect for when you want to spend less on where you sleep and more on seeing the sights, these stays come with the basics like fresh towels and linens, and simple breakfast options.
For a low-cost and no-fuss stay, check out Skyline Motel. It has a 2-star rating and amenities including internet access and heating.
Best Western Plus Chicagoland - Countryside offers 3-star value. Practical perks including a lift and a microwave are there to make your Westchester hotel stay more seamless.
A restaurant and ATMs are only a sample of what's offered at Courtyard Chicago Elmhurst/Oakbrook Area. Another win for your bottom line, this place is rated 3 stars.
Best 4-star hotels in Westchester
Searching for hotels in Westchester with more than just the essentials? A 4-star stay hits the mark. With around ten to select from, they come with appealing extras like cocktail bars, wellness centers, and airport shuttles. You get higher quality without the higher price.
Book a room at The Drake Oak Brook, Autograph Collection and experience the elevated standards that come with this 4-star stay. Take advantage of a nightclub and a golf course while you're here.
Another Westchester hotel to consider is DoubleTree by Hilton Chicago O'Hare Airport-Rosemont. It offers thoughtful amenities such as car rental options and concierge assistance.
DoubleTree by Hilton Chicago Midway Airport, IL is also easy to like. It makes a great impression with a pool, concierge assistance and more.
Best hotels in Westchester for families
Family trips can be chaotic, but your hotel should be the stress-free part. You'll find roughly ten family-friendly hotels in Westchester that balance what kids want and adults need. These stays often come with handy features like adjoining rooms, kitchenettes, cribs, and kids' menus.
Save more for fun activities with the kids when you book Holiday Inn Express & Suites Chicago West-O'Hare Arpt Area by IHG. This affordable 2-star option has amenities like luggage storage and a safe deposit box.
If you'd like a little more luxury, spoil the kids (and yourself) with a stay at Loews Chicago O'Hare Hotel. This 4-star Westchester hotel features air conditioning and a restaurant.
Another option is Crowne Plaza Lombard Downers Grove. Offering a 24-hour front desk and a fitness center, this stay is a favorite for a reason.
Best hotels with a spa
Let calm find you at one of the ten or so Westchester hotels with a spa. They feature anything from hot tubs to gyms and thermal pools. Throw in meditation classes, massages, and manicures and you're on your way to bliss.
Get the break you deserve at Le Méridien Chicago - Oakbrook Center. This 4-star accommodation option comes with all the right perks, including a spa and room service.
Comfort Suites Oakbrook Terrace Near Oakbrook Center is another top choice where you can treat yourself to some TLC. Make the most of a fitness center and a lounge at this 3-star hotel in Westchester.
After checking in to Sybaris Pool Suites, you'll wonder why you ever stayed anywhere else. This option features amenities like a spa and a fireplace.
Best hotels with a pool
Add a splash of fun to your getaway with a pool. If you pick a city hotel, expect indoor or rooftop options. Resorts? They usually go big with sprawling outdoor layouts and the occasional swim-up bar. There are at least 40 pool hotels in Westchester perfect for your next escape.
Make relaxing poolside a priority at Hampton Inn Chicago-O'Hare Int'l. Airport. With an indoor swimming pool, a fitness center and a bar, this Westchester hotel invites you to slow down and enjoy your time away.
Hampton Inn & Suites Chicago Burr Ridge also guarantees you a good time. Settle into this popular option and take advantage of an indoor swimming pool, a lobby bar and air conditioning.
Courtyard Chicago Midway Airport is another stay that delivers everything you want. This hotel has an indoor swimming pool, express check-out and a fitness center.
Best pet-friendly hotels
Taking a trip with your furry friend? Pet-friendly hotels often offer cozy pet beds, bowls, and outdoor areas to run around. Some even go the extra mile with things like grooming or washing stations. With around 50 Westchester hotels that welcome pets, your little pal can tag along too.
Check in with your sidekick at DoubleTree by Hilton Chicago O'Hare Airport-Rosemont. You'll find conveniences here like valet parking and shuttle services.
Hampton Inn Chicago-Midway Airport is another place where four paws are as welcome as two feet. This accommodation option comes with air conditioning and internet access.
Aloft Chicago O'Hare will have you all settled in no time. Its amenities include a fitness center and internet access.
