Kendall County Vacations & Trips from ￥181,684

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The Latest Kendall County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was ￥204,466, price is now ￥181,684 per person
￥181,684
per person
Dec 26 - Dec 31
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (3,575 reviews)
The location was great with the magnificent mile a minute walk away, the beach is also only a 5 minute walk. Breakfast was really good with all the usual options and the room was clean and cozy I would stay again!

Reviewed on Oct 6, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥256,936, price is now ￥194,809 per person
￥194,809
per person
Dec 26 - Dec 31
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Cleaning staff amazing! Great proximity to everything on Michigan Ave! Starbucks across the street along with Garrett’s popcorn !

Reviewed on Oct 6, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥304,531, price is now ￥253,332 per person
￥253,332
per person
Nov 28 - Nov 30
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Downtown Chicago
Price was ￥223,512, price is now ￥197,892 per person
￥197,892
per person
Dec 26 - Dec 31
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,346 reviews)
I've stayed at other Hyatt Hotels but this was a first in Chicago and definitely not the last!

Reviewed on Oct 5, 2025

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥210,144, price is now ￥186,560 per person
￥186,560
per person
Dec 26 - Dec 31
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (1,705 reviews)
Great location, however one of our windows in our room wouldn’t close all the way so it made it very loud being by the hospital. And if staying with someone, I hope you’re close because you can see straight to the toilet with the door shut! Otherwise, great location, friendly staff, clean.

Reviewed on Oct 5, 2025

Kendall County Hotel Deals

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 ￥12,327 per night from Oct 29 to Oct 30
￥12,327
￥13,681 total
Oct 29 - Oct 30
includes taxes & fees
8.8/10 Excellent! (2,269 reviews)
"Great price, great motel and staff was great."

Reviewed on Oct 2, 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 ￥10,655 per night from Oct 8 to Oct 9
￥10,655
￥11,825 total
Oct 8 - Oct 9
includes taxes & fees
7/10 Good! (1,301 reviews)
"Love it"

Reviewed on Sep 28, 2025

Chicago Club Inn & Suites
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 ￥13,140 per night from Nov 3 to Nov 4
￥13,140
￥17,612 total
Nov 3 - Nov 4
includes taxes & fees
8.4/10 Very Good! (1,273 reviews)
"The staff was friendly, room was perfect for the occasion."

Reviewed on Oct 5, 2025

The Champagne Lodge & Luxury Suites
See all 893 properties in Kendall County
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.

Frequently asked questions

How much does a Kendall County vacation package cost?
Starting from as low as ￥181,684, you can handcraft your own Kendall County package the way you want. Simply combine hotels, flights and rental cars and we'll reward you with discounts.
How do I get a cheap travel package to Kendall County?
Our Kendall County vacation packages promise plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (including activities) into one neat package. But great bargains are just the beginning of your next big adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotels around the world to select from. No matter your budget, there's a package with your name on it.
What are the top hotels in Kendall County?
If you're headed to Oswego, you can't go past Best Western Chicago - Downers Grove and Motel 6 Naperville, IL. Both are comfortable bases for exploring this exciting Kendall County city.
How far in advance should I book my Kendall County vacation?
Savvy travelers will likely want to book early. You can generally compare international airfares on Expedia up to 12 months before your flight. If you've left booking to the last minute, don't stress. Budget prices sometimes become available just weeks prior to departure.
What does an Expedia Kendall County travel package include?
That depends on you. You can pick from a variety of Kendall County bundles, such as a flight, hotel and rental car. You can also book a flight with a hotel, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like activities and tours. Whatever your dream Kendall County trip looks like, you're sure to save!
What should I know before booking a Kendall County travel package?
Whether it's adventure or relaxation you're seeking, a Kendall County vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Kendall County Expedia vacation package?
With a vacation package, you're always in charge. Whether you're hoping to fly to Kendall County in economy or business class, simply select from the available airline options. Expedia has access to more than 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Kendall County vacation package?
Because we understand life can be unpredictable, the answer is yes. To learn more, head to our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.