Equestrian Estates Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Equestrian Estates Vacation

Save time and energy on your travel planning by booking a Equestrian Estates vacation package. One of the best neighborhoods to stay in this vibrant city is Clarendon Hills, which is good for golfing and a lot more. Make your trip to Equestrian Estates even more enjoyable by including some sightseeing. Cog Hill Golf & Country Club, Ruffled Feathers Golf Course and Gleneagles Country Club are among the top attractions you'll want to explore. Stop daydreaming and start adventuring. Browse the many options on Expedia today and finally put your Equestrian Estates vacation plans into action!

Top Equestrian Estates Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,352, price is now CA $941 per person
CA $941
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,898, price is now CA $1,336 per person
CA $1,336
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,068, price is now CA $756 per person
CA $756
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 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 CA $1,284, price is now CA $938 per person
CA $938
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Everything was nice. The room was clean and a nice size but it’s the views that make it worthwhile! Waking up & seeing the beautiful sunrise over the lake was amazing!!

Reviewed on Nov 11, 2026

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Equestrian Estates Hotel Deals

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 CA $90 per night from Dec 10 to Dec 11
CA $90
CA $100 total
Dec 10 - Dec 11
includes taxes & fees
Chicago Club Inn & Suites
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 CA $127 per night from Nov 12 to Nov 13
CA $127
CA $141 total
Nov 12 - Nov 13
includes taxes & fees
9/10 Wonderful! (3,135 reviews)
"Clean room and good bed. Good full breakfast."

Reviewed on Nov 11, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
70 Yorktown Center Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Nov 22 to Nov 23
CA $199
CA $220 total
Nov 22 - Nov 23
includes taxes & fees
The Westin Chicago Lombard
See all 1,650 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.
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What to do in Equestrian Estates

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Equestrian Estates

Frequently asked questions

How much does an Equestrian Estates vacation package cost?
Offering excellent value package deals from CA $671 on Expedia, you'll be pleasantly surprised at how much a vacation to Equestrian Estates costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Equestrian Estates?
You can usually find lower rates and better availability in January, February and November. Explore our cheap Equestrian Estates vacation packages and you could land some great off-season deals.
How many days is enough for Equestrian Estates?
With a well-organized travel plan, you can easily visit the top Equestrian Estates attractions in a handful of days. But if you prefer to venture off the beaten track or take day trips, consider booking your Equestrian Estates vacation for longer.
How to find the best Equestrian Estates package deals?
Use Expedia's filters to help you find some of the best Equestrian Estates package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Equestrian Estates package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book an Equestrian Estates vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking accommodations and flights separately. Better still, you can customize your Equestrian Estates trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Equestrian Estates?
If you're considering a spur-of-the-moment Equestrian Estates vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Equestrian Estates?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Equestrian Estates.
  2. Plan your budget wisely: In addition to the cost of your stay, you'll need to consider other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that may arise during your trip to Equestrian Estates.
  3. Decide how long to go away for: Now that you're up to speed on Equestrian Estates, you can work out the right length of your vacation. Put together a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the right 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.