Equestrian Estates Vacation Packages

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,389, price is now CA $921 per person
CA $921
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The room was small, but fine. The bed was comfortable. The TV was too big so it covered the thermostat control panel, and the remote Guide button didn’t work. Also, the water pressure in the shower was super weak… glad I didn’t need to wash my hair. But location, general vibe, and staff were great.

Reviewed on Jul 8, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!

Reviewed on Jul 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,047, price is now CA $1,235 per person
CA $1,235
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on Jul 8, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,110, price is now CA $1,436 per person
CA $1,436
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
I stay at this hotel every time I'm in Chicago. The staff never change and they remember me. They're always friendly and seem to really enjoy their jobs. The hotel is always clean and I never encounter any problems.

Reviewed on Jul 8, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Great location can get a bit noisy but really nice hotel.

Reviewed on Jul 8, 2026

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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 CA $202 per night from Jul 19 to Jul 20
CA $202
CA $251 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,022 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
The price is CA $125 per night from Aug 3 to Aug 4
CA $125
CA $139 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (2,866 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 CA $111 per night from Jul 26 to Jul 27
CA $111
CA $123 total
Jul 26 - Jul 27
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 1,581 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 $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $58
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 $921 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.

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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.