Equestrian Woods Vacations from ¥58,476

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The Latest Equestrian Woods Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥58,476
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
The staff was extremely accommodating, it was marathon week so I understand things can be tough, my issues were with the room as a whole. The shower would leak into the bathroom and completely cover the floor and when I informed staff I was having flooding problems they said oh it’s the shower curtain as if it’s a common issue. The wall paper in the bathroom was peeling off the wall. Tv guide didn’t work so you get to play channel roulette. On the plus side staff was great and they provided cold drinks in the morning, ac works really well

Reviewed on Oct 14, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
¥137,816
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Clean space to relax and enjoy your trip

Reviewed on Oct 15, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥70,021
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
From the second we pulled up and used the valet service, every single part of our stay was spectacular:) We would highly recommend!

Reviewed on Oct 15, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥66,276
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Everyone was so nice and accommodating. The location is great. We had a great view of the river.

Reviewed on Oct 15, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
¥77,137
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)

Find the Best Equestrian Woods Vacation Packages

Equestrian Woods Hotel Deals

Chicago Club Inn & Suites

Chicago Club Inn & Suites

630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
¥10,078
¥11,185 total
Nov 15 - Nov 16
includes taxes & fees
Chicago Club Inn & Suites
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
¥15,301
¥16,981 total
Oct 22 - Oct 23
includes taxes & fees
SureStay Plus Hotel by Best Western Chicago Lombard
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
¥14,391
¥16,906 total
Nov 8 - Nov 9
includes taxes & fees
8/10 Very Good! (2,164 reviews)
"Use of the shuttle was extremely helpful! Stowaway for bags prior to check in was great Room clean and comfortable. Shuttle was on time and hotel is near the midway airport- so quick!"

Reviewed on Oct 15, 2026

Sleep Inn Midway Airport Bedford Park
See all 1,753 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

¥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

¥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

¥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Equestrian Woods

Frequently asked questions

How much does an Equestrian Woods vacation package cost?
You can pick up a vacation package to this destination from ¥58,476 on Expedia. However, how much your vacation to Equestrian Woods costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Equestrian Woods?
You can usually find lower rates and better availability in January, February and November. Check out our cheap Equestrian Woods vacation packages and you could score some excellent off-season deals.
How many days is enough for Equestrian Woods?
Usually, a handful of days is enough to see the top sights during your Equestrian Woods vacation. However, if you'd like to have more time to chill out or go on 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. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add a couple of filters and see 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 affordable Equestrian Woods package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book an Equestrian Woods vacation as a package?
You can enjoy significant savings on your next Equestrian Woods retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. 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 Woods?
If you have your Equestrian Woods travel dates confirmed, book early to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Equestrian Woods?
  1. Pick your dates: What you'd like to do in Equestrian Woods and your preferred season can help you decide when to travel.
  2. Budget wisely: In addition to the price of your stay, you'll need to factor in other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may come up during your trip to Equestrian Woods.
  3. Decide how long to go for: Now that you're more familiar with Equestrian Woods, you can work out the ideal length of your vacation. Create a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your airfare and accommodations: After you've settled on your dates and duration, book the ideal Equestrian Woods 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.