Equestrian Estates Vacations from ¥286,880

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The Latest Equestrian Estates Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥286,880
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Great stay

Reviewed on Aug 23, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥357,160
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Everything was outstanding!

Reviewed on Aug 23, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥586,192
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥642,213
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,348 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥462,080
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)

Find the Best Equestrian Estates Vacation Packages

Equestrian Estates Hotel Deals

Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
¥9,998
¥11,196 total
Aug 30 - Aug 31
includes taxes & fees
Red Roof Inn PLUS+ Chicago - Willowbrook
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL
Fully refundable
¥18,120
¥22,860 total
Sep 8 - Sep 9
includes taxes & fees
8.2/10 Very Good! (1,031 reviews)
"The hotel is very clean. Our room was fantastic! It did take about 10 minutes for anyone to come check us in, but we can't assume there wasn't something else going on we didn't know about."

Reviewed on Aug 24, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Chicago Club Inn & Suites

Chicago Club Inn & Suites

630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
¥8,901
¥9,879 total
Sep 22 - Sep 23
includes taxes & fees
Chicago Club Inn & Suites
See all 1,643 properties in Equestrian Estates
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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Equestrian Estates

Frequently asked questions

How much does an Equestrian Estates vacation package cost?
You can grab a vacation package to this popular destination from ¥286,880 on Expedia. But how much your vacation 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 vacation 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 vacation. 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 vacation as a package?
You can enjoy significant savings on your Equestrian Estates getaway by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation 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?
  1. 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.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodations will probably be the biggest expense during your trip to Equestrian Estates.
  3. 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.
  4. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Equestrian Estates vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.