Equestrian Woods Vacation Packages

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Your Equestrian Woods Vacation

Organizing your next exciting break is a walk in the park with a Equestrian Woods vacation package. The neighborhood of Clarendon Hills, which is good for golfing, makes a superb base to uncover the wonders of this vibrant city. If your trip to Equestrian Woods includes some sightseeing, drop by famous attractions like Cog Hill Golf & Country Club, Ruffled Feathers Golf Course and Gleneagles Country Club. Don't put off exploring this destination any longer. Your perfect Equestrian Woods vacation is a few quick clicks away with Expedia.

Top Equestrian Woods Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
CA $1,002
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,146 reviews)
Location was amazing. A few changes and the hotel could be great. Big trash barrels on my floor as you get ioff elevator on your floor. Yuck. Elevators painfully slow. No real amenities. Staff was ok. Could have bumped up friendliness a few notches. Though my check out girl was very nice. Rooms fairly new. I might stay there again but idk.

Reviewed on Aug 30, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $2,303
per person
Oct 21 - Oct 28
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,968
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,212
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Great stay.

Reviewed on Aug 30, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,140
per person
Oct 25 - Oct 28
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)

Ready to book your vacation to Equestrian Woods?

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Equestrian Woods Hotel Deals

Chicago Club Inn & Suites

Chicago Club Inn & Suites

630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
CA $78
CA $86 total
Sep 29 - Sep 30
includes taxes & fees
Chicago Club Inn & Suites
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL
Fully refundable
CA $177
CA $221 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very good! (1,013 reviews)
"Na"

Reviewed on Aug 30, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $159
CA $186 total
Sep 23 - Sep 24
includes taxes & fees
8/10 Very good! (2,090 reviews)
"Great last minute stay. Clean and staff was great."

Reviewed on Aug 30, 2026

Sleep Inn Midway Airport Bedford Park
See all 1,712 properties in Equestrian Woods
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 Woods

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
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 $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Equestrian Woods

Frequently asked questions

How much does an Equestrian Woods vacation package cost?
You can grab a vacation package to this popular destination from CA $1,002 on Expedia. However, how much your vacation to Equestrian Woods costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Equestrian Woods?
If you're hoping to snag a cheap Equestrian Woods vacation package, consider planning a trip in January, February and November. You'll generally find lower rates on flights and accommodations during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Equestrian Woods?
Typically, a handful of days is enough to visit the major sights during your Equestrian Woods vacation. But if you prefer to have time to kick back or take day trips, consider extending your itinerary.
How to find the best Equestrian Woods package deals?
Bagging a cheap Equestrian Woods package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Equestrian Woods package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book an Equestrian Woods vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can tailor your Equestrian Woods getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Equestrian Woods?
If you're considering a spur-of-the-moment Equestrian Woods vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Equestrian Woods?
  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 visit Equestrian Woods.
  2. Set your budget: Consider expenses such as transportation, flights and meals when calculating how much to set aside for your trip to Equestrian Woods. Then, pick a hotel that suits your budget, whether that's an affordable option or a more upscale getaway.
  3. Decide how long to go for: Now that you know more about Equestrian Woods, you can work out the ideal length of your break. Create a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find an Equestrian Woods vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.