Equestrian Estates Vacations from ￥374,634

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The Latest Equestrian Estates Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was ￥493,372, price is now ￥374,634 per person
￥374,634
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,139 reviews)
Incredible hotel. Loved the stay!

Reviewed on Jul 8, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥562,542, price is now ￥416,023 per person
￥416,023
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥512,352, price is now ￥383,981 per person
￥383,981
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
View was beautiful, accommodations were excellent.

Reviewed on Jul 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥647,891, price is now ￥485,509 per person
￥485,509
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We had our room upgraded to a suite which was a nice surprise. It was a great stay!

Reviewed on Jul 8, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was ￥561,004, price is now ￥427,625 per person
￥427,625
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Good location.

Reviewed on Jul 3, 2026

Find the Best Equestrian Estates Vacation Packages

Equestrian Estates Hotel Deals

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥19,752 per night from Jul 12 to Jul 13
￥19,752
￥24,813 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very Good! (1,023 reviews)
"Don’t like Parking fee."

Reviewed on Jul 7, 2026

Holiday Inn Chicago – Midway Airport S by IHG
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is ￥14,270 per night from Aug 5 to Aug 6
￥14,270
￥15,837 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (2,868 reviews)
"Great, always stay there"

Reviewed on Jul 8, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is ￥12,739 per night from Jul 19 to Jul 20
￥12,739
￥14,139 total
Jul 19 - Jul 20
includes taxes & fees
7.2/10 Good! (1,642 reviews)
"Comfortable bed, but linens not so much. Very scratchy. Breakfast was good as well. The location was perfect. Overall, the property is a little shabby and it smells like the guests are not obeying the signs posted outside their doors about vaping and marijuana."

Reviewed on Jul 8, 2026

Chicago Club Inn & Suites
See all 1,585 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

￥3,887
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,853
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,398
per adult
92% of travellers recommend
Art Institute of Chicago
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 ￥374,634 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.