Equestrian Estates Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Equestrian Estates Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$989, price is now S$696 per person
S$696
per person
17 Oct - 20 Oct
found 20 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,418 reviews)
I think this is a good hotel in an extremely convenient location whether you plan to walk or catch a ride. Close to everything and staff was pleasant.

Reviewed on 19 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,791, price is now S$1,134 per person
S$1,134
per person
17 Oct - 20 Oct
found 20 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,043, price is now S$1,388 per person
S$1,388
per person
17 Oct - 20 Oct
found 20 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,206, price is now S$848 per person
S$848
per person
17 Oct - 20 Oct
found 20 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,382, price is now S$984 per person
S$984
per person
17 Oct - 20 Oct
found 20 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (2,837 reviews)
Property was well located to be able to explore Chicago easily. Very clean hotel and the staff was extremely accommodating. The only thing missing was a pool but it wasn’t a huge issue. Very nice hotel and would go back for sure.

Reviewed on 20 Aug, 2025

Top hotels in Equestrian Estates

DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is S$119 per night from 31 Aug to 1 Sept
S$119
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (1,085 reviews)
"It was great and clean"

Reviewed on 17 Aug, 2025

DoubleTree by Hilton Lisle Naperville
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 S$102 per night from 16 Sept to 17 Sept
S$102
16 Sept - 17 Sept
includes taxes & fees
8.8/10 Excellent! (2,189 reviews)
"The rooms were nice if a bit dated. Everything was clean and we had a fantastic stay. Special thanks to Patrick at the front desk for leaving a great lasting impression. Super helpful and friendly staff! Would highly recommend."

Reviewed on 18 Aug, 2025

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 S$109 per night from 21 Sept to 22 Sept
S$109
21 Sept - 22 Sept
includes taxes & fees
7/10 Good! (1,239 reviews)
"We have stayed here several times and it has been nice. The property needs maintenance such as regular grooming of the grass and shrubs."

Reviewed on 17 Aug, 2025

Chicago Club Inn & Suites
See all 1,460 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Equestrian Estates

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
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 holiday package cost?
You can grab a holiday package to this popular destination from S$696 on Expedia. But how much your holiday to Equestrian Estates costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Equestrian Estates?
If you're looking to score a cheap Equestrian Estates holiday package, consider planning a trip in January, February and November. You'll generally find better prices on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Equestrian Estates?
Typically, a handful of days is enough to go to the top attractions during your Equestrian Estates holiday. However, if you prefer to have time to unwind or take day tours, think about extending your trip.
How to find the best Equestrian Estates package deals?
Start your search for an Equestrian Estates package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Equestrian Estates package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Equestrian Estates escape off to a flying start.
Is it cheaper to book an Equestrian Estates holiday as a package?
You can enjoy significant savings on your Equestrian Estates getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Equestrian Estates?
If you have your Equestrian Estates travel dates locked in, book early to score some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Equestrian Estates?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Equestrian Estates.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodation will probably be the biggest expense during your trip to Equestrian Estates.
  3. Decide how long to go for: Now that you know more about Equestrian Estates, you can figure out the perfect length of your break. Create a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your accommodation and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Equestrian Estates holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.