Equestrian Estates Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $959, price is now CA $673 per person
CA $673
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,237, price is now CA $873 per person
CA $873
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.

Reviewed on Feb 9, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,396, price is now CA $1,002 per person
CA $1,002
per person
Apr 25 - Apr 29
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Love the room! Very ritzy!!

Reviewed on Feb 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,401, price is now CA $1,033 per person
CA $1,033
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,603, price is now CA $1,188 per person
CA $1,188
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

Ready to book your vacation to Equestrian Estates?

 

Choose your dates

Equestrian Estates Hotel Deals

Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
4021 North Mannheim Rd Schiller Park IL
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Feb 18 to Feb 19
CA $97
CA $111 total
Feb 18 - Feb 19
includes taxes & fees
8.2/10 Very Good! (2,331 reviews)
Room was clean, friendly staff.

Reviewed on Feb 6, 2026

Sonesta Simply Suites Chicago O'Hare Airport
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
The price is CA $138 per night from Feb 10 to Feb 11
CA $138
CA $180 total
Feb 10 - Feb 11
includes taxes & fees
8.4/10 Very Good! (1,392 reviews)
Everything was outstanding

Reviewed on Feb 3, 2026

The Champagne Lodge & Luxury Suites
Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District

3.5 out of 5
1835 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Feb 16 to Feb 17
CA $138
CA $162 total
Feb 16 - Feb 17
includes taxes & fees
9/10 Wonderful! (1,378 reviews)
The staff working at the front desk were lovely and so helpful! The room was very clean and I enjoyed my stay. I only wished that the lights in the room/bathroom didn't automatically turn off every 20 minutes, that got a little frustrating especially when in the shower.

Reviewed on Feb 6, 2026

Hyatt House Chicago Medical/University District
See all 1,644 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Equestrian Estates

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Equestrian Estates

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Equestrian Estates

Explore a world of travel with Expedia

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