Kendall County Holidays

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    Save up to €185 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top destinations in Kendall County

FlightsFlightsHotelsHotels

Oswego

Oswego

Top Flight + Hotel Deals in Kendall County

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Doorman was delightful! King room was spacious. Toilet flush was problematic. The pool was not open despite the advertisement on the Expedia websit. Lots of additional, non-negotiable charges once you get there.

Reviewed on 11 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on 11 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) 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
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
We enjoyed the rooftop dining--the view is terrific, especially after dark. Excellent location on Michigan Ave near restaurants, shopping and museums. Did the valet parking and it worked well for us. The service was all around excellent including checkin/checkout, in room dining service (we did breakfast), concierge, baggage help and valet . They were able to give us a late check out so we could fit in an architectural boat tour and then kept our luggage all day until evening so we could squeeze more out of this long weekend trip to the Windy City. The hotel is clean, stylish and service is top rate. I would highly recommend this hotel.

Reviewed on 11 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Beautiful hotel in great location. The food option at hotel are great with good food. It is walkable to surrounding attractions.

Reviewed on 10 Aug 2025

Top hotels in Kendall County

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 €73 per night from 13 Aug to 14 Aug
€73
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (2,184 reviews)
"everything was good"

Reviewed on 11 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 €65 per night from 11 Sept to 12 Sept
€65
11 Sept - 12 Sept
includes taxes & fees
7/10 Good! (1,242 reviews)
"I liked the accessibility to the pool."

Reviewed on 9 Aug 2025

Chicago Club Inn & Suites
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 €79 per night from 24 Aug to 25 Aug
€79
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,067 reviews)
"Friendly staff. Conveniently located"

Reviewed on 9 Aug 2025

DoubleTree by Hilton Lisle Naperville
See all 877 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 holiday package cost?
Starting from as low as €727, 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 holiday 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 holiday?
Savvy travellers 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 holiday 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 holiday package?
With a holiday 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 holiday 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.