Equestrian Estates Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Equestrian Estates
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
S$203
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very good! (1,007 reviews)
"We arrived super late and the front desk was exceptional! Amazing stay! 10/10 will return to this hotel on our next visit"
Reviewed on 28 Aug, 2026
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
S$132
30 Aug - 31 Aug
includes taxes & fees
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
S$90
6 Sept - 7 Sept
includes taxes & fees
6.4/10 (1,252 reviews)
"no coffee in the room"
Reviewed on 28 Aug, 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.
What to do in Equestrian Estates
Chicago: Navy Pier Centennial Wheel Ticket
S$32
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
S$52
per adult
94% of travellers recommend
Frequently asked questions
How much does an Equestrian Estates holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday to Equestrian Estates costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Equestrian Estates?
If you're looking to score a cheap Equestrian Estates holiday package, consider planning a trip in January, February and November. You'll generally find better prices on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Equestrian Estates?
Typically, a handful of days is enough to go to the top attractions during your Equestrian Estates holiday. However, if you prefer to have time to unwind or take day tours, think about extending your trip.
How to find the best Equestrian Estates package deals?
Start your search for an Equestrian Estates package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Equestrian Estates package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Equestrian Estates escape off to a flying start.
Is it cheaper to book an Equestrian Estates holiday as a package?
You can enjoy significant savings on your Equestrian Estates getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Equestrian Estates?
If you have your Equestrian Estates travel dates locked in, book early to score some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Equestrian Estates?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Equestrian Estates.
- Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodation will probably be the biggest expense during your trip to Equestrian Estates.
- Decide how long to go for: Now that you know more about Equestrian Estates, you can figure out the perfect length of your break. Create a draft itinerary and allocate enough time to cover everything you want to do.
- Combine your accommodation and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Equestrian Estates holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
