Equestrian Estates Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Equestrian Estates Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$775
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$1,165
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$1,244
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Everything
Reviewed on Aug 29, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$1,055
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
This hotel truly exceeded my expectations and checked every box. From the moment we arrived, the property felt luxurious, stylish, and beautifully maintained. The accommodations were wonderful, and the attention to detail throughout the hotel really made the stay feel special.
The location was also excellent and made it convenient to enjoy everything the area had to offer. The rooftop was absolutely magnificent, the bar had a great atmosphere, and our room was spotless and refreshed every day.
What stood out most was the way the staff cared for their guests. Everyone was friendly, attentive, welcoming, and always willing to help. I did experience one minor issue during my stay, but it was handled quickly and professionally, which I truly appreciated.
Everything seemed to run like a well-oiled machine. Between the luxurious atmosphere, great location, beautiful rooftop, cleanliness, and outstanding service, this was an exceptional stay. I will definitely be returning!
Reviewed on Aug 28, 2026
Eurostars Magnificent Mile
Downtown Chicago
$898
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Excellent location and staff was friendly and very helpful. Elevators made funny noises though. Kinda scary. Still recommend.
Reviewed on Aug 28, 2026
Swissotel - Chicago
Downtown Chicago
$1,065
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
My sister and I came to Chicago from Baltimore to see the Obama Presidential Center. When I researched hotels to stay at in Chicago I was very impressed with Swissotel ratings. I could’ve made a better choice. We didn’t get to see everything we wanted to see, but when we do come back to Chicago Swissotel is definitely where we’ll be staying. So if you’re planning on coming to Chicago Swissotel is the best choice.
Reviewed on Aug 29, 2026
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See all available trips from Columbus to Equestrian Estates
View all tripsEquestrian Estates Vacation Packages
Trying to plan a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Equestrian Estates vacation packages can help. We're here to book everything you'll need to make your Equestrian Estates trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. AARP Travel Center has an amazing list of flights and hotels, as well as local activities to select from.
Hotel Deals in Equestrian Estates
With 1630 hotels and resorts in Equestrian Estates to choose from, you will find one that is perfect for you.
We have fantastic rates on everything from family-friendly resorts that check off all the vacation must-haves to affordable hotels perfect for those on a budget. You can look through all the possibilities and choose the lodging that is ideal for you. With AARP Travel Center's Equestrian Estates hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Equestrian Estates
The fact that you are traveling to Equestrian Estates means your trip will already be off to a fantastic start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
You can also check out our "Things to Do" page for more inspiration or to reserve an activity in Equestrian Estates.
Package Your Equestrian Estates Vacation and Save
With so much to see and do in Equestrian Estates, you'll be wanting to plan your outings, not devoting time to searching for the cheapest hotel. The AARP Travel Center Powered by Expedia® allows you to easily get everything you need, and save some cash doing it. You can plan your entire holiday, including activities in Equestrian Estates from just one place. So what are you waiting for? Bundle today and save!
Top Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr Naperville IL
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Quality Inn O'Hare Airport
3801 North Mannheim Road Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff ...
Embassy Suites by Hilton Chicago Lombard Oak Brook
707 E Butterfield Road Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
The Westin Chicago Lombard
70 Yorktown Center Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Harborside International Golf Center and Martin Luther ...
Motel 6 Bridgeview, IL
9625 S 76th Ave Bridgeview IL
Stay at this motel in Bridgeview. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Carleton of Oak Park
1110 Pleasant St Oak Park IL
Book a stay at this boutique hotel in Oak Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our ...
William Tell Hotel MOD Collection by Sonesta
6201 Joliet Rd Countryside IL
Book a stay at this business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the clean ...
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Book a stay at this luxury resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Ravisloe Country Club and Oak Hill ...
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Don't see what you're looking for?
See all available properties in Equestrian Estates
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 14 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 3 hours ago
Wed, Oct 14 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183
Roundtrip
found 3 hours ago
Thu, Oct 1 - Sun, Oct 4
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197
Roundtrip
found 5 days ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 2 hours ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 2 hours ago
Best points of interest in Chicago
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