Equestrian Estates Holidays from £986

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Your Equestrian Estates Holiday

Save time and energy on your travel planning by booking a Equestrian Estates holiday package. One of the best neighbourhoods 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 holiday plans into action!

Top Equestrian Estates Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£986
per person
12 Nov - 16 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Location and facility was very nice

Reviewed on 7 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,175
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The property was nice with fairly convenient parking, only about a 5 min walk from the nearest in/out garage. If I had to nitpick, I’d say the only thing I’d add is a fan (or two) to the gym room. When using the treadmills you end up sweating as if you were in a sauna!

Reviewed on 8 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£2,039
per person
28 Nov - 5 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,268
per person
15 Oct - 19 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,197
per person
15 Oct - 19 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
The pool & jacuzzi was perfect, this hotel is beautiful

Reviewed on 7 Sept 2026

Equestrian Estates Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Cog Hill Golf & Country Club, Ruffled Feathers Golf Course and Gleneagles Country Club

Top hotels in Equestrian Estates

Chicago Club Inn & Suites

Chicago Club Inn & Suites

630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
£52
8 Oct - 9 Oct
includes taxes & fees
7.2/10 Good! (1,791 reviews)
"Room was not spotless and there we stains on the bedding. trash was not picked up. bathroom had humidity smell. the inners yard was full of overgrown plans and weeds. pool did not seem functional."

Reviewed on 8 Sept 2026

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
£139
27 Sept - 28 Sept
includes taxes & fees
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
£92
4 Oct - 5 Oct
includes taxes & fees
8/10 Very good! (2,107 reviews)
"As soon as we got to the room there was a strong odor of urine and the carpet left the bottoms of our socks black. There were also stains on the walls. I do not recommend"

Reviewed on 8 Sept 2026

Sleep Inn Midway Airport Bedford Park
See all 1,646 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.

What to do in Equestrian Estates

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Equestrian Estates

Frequently asked questions

Why should I book my Equestrian Estates holiday with Expedia?
Expedia has your back for all aspects of your upcoming Equestrian Estates trip. You'll always get the best deals, but when you bundle your hotel, flights and/or hire car into a holiday package, you'll get even bigger savings. Looking to truly make the most of your adventure? Add a few fun tours and activities to your customised package. We offer flexible cancellation policies on almost all bookings, so you won't need to worry if you have to change your plans. Visit our Customer Service Portal link to discover more.
When is the best time of year to holiday in Equestrian Estates?
Equestrian Estates is at its busiest in March, May and June. If you want a more relaxed getaway, go there in December, January and February. With average daytime temperatures of -4ºC, January is the coolest period in Equestrian Estates. The warmest month is July, when you can experience average temperatures of 23ºC throughout the day. Whatever the weather, you'll discover plenty of things to keep you occupied here.
How do I get a cheap holiday to Equestrian Estates?
If you love landing a bargain, bundle your bookings into an Equestrian Estates holiday. Whether you're chasing hotels, flights, activities or hire cars, you can browse and book them all in one place. You'll have loads of choice at your fingertips too. Expedia has over 400 air carriers and 321,000 hotel options around the globe to choose from. Fly with who you prefer, stay where you like and save a pretty penny — now that's the perfect escape! Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Equestrian Estates holiday?
Kick-start your holiday in Equestrian Estates by visiting Cog Hill Golf & Country Club, Ruffled Feathers Golf Course and Gleneagles Country Club. They are just some of the top attractions in this vibrant city.
Do I need a visa for my Equestrian Estates holiday?
Official government websites have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for your visit, whether it be for work or pleasure, will determine if you'll need a visa for Equestrian Estates. Be sure that your passport is up to date and has a minimum of six months validity remaining after your intended return date. Do all your travel planning ahead of time to avoid any last-minute surprises.
What should I wear on my Equestrian Estates holiday?
Though everyone's fashion style differs, it can help to have a few guidelines for what to bring on your holiday in Equestrian Estates. We recommend looking up social media before you head off so you can blend in like a local. Pack with confidence by monitoring the local weather conditions in Equestrian Estates. July brings the warmest temperatures, with daily averages of 23ºC, while January days average -4ºC, making it the coolest time of year.
What does an Expedia Equestrian Estates holiday include?
That depends entirely on you. Simply select from a range of Equestrian Estates bundles, such as a hotel, flight and hire car. You can also book a flight and a hotel, or a flight and a car hire. Once you've made your booking, add on the fun stuff like experiences and tours. Whatever your perfect Equestrian Estates trip looks like, you're sure to save! You'll always have the flexibility and freedom to plan your holiday any way you want with Expedia.
Does Expedia offer Book Now, Pay Later Equestrian Estates holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book your dream getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Consider one of these flexible payment options:
  • Pay monthly holidays: Klarna offers the ability to pay in multiple instalments that suit all types of budgets, so you can book that well-deserved holiday sooner.
  • No-deposit holidays: When you stumble on an incredible deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your escape.
Can I choose my airline with an Equestrian Estates Expedia holiday?
Expedia offers access to more than 400 airline partners globally, so you certainly can. Just pick the carrier that suits you and create your ideal Equestrian Estates trip.

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. Flight-inclusive packages are ATOL protected.