Kendall County Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top destinations in Kendall County

View along the Fox River.
FlightsFlightsHotelsHotels

Oswego

Oswego

Top Flight + Hotel Deals in Kendall County

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,735, price is now €1,160 per person
€1,160
per person
23 Jun - 28 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on 25 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was €2,109, price is now €1,410 per person
€1,410
per person
23 Jun - 28 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on 27 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €2,415, price is now €1,681 per person
€1,681
per person
23 Jun - 28 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
Absolutely fantastic will be back

Reviewed on 27 Apr 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was €1,956, price is now €1,376 per person
€1,376
per person
23 Jun - 28 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,663 reviews)
bar selection and staff wonderful

Reviewed on 28 Apr 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,853, price is now €1,310 per person
€1,310
per person
23 Jun - 28 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on 24 Apr 2026

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 €79 per night from 13 May to 14 May
€79
13 May - 14 May
includes taxes & fees
9/10 Wonderful! (2,703 reviews)
Good stay.

Reviewed on 29 Apr 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
The price is €58 per night from 7 May to 8 May
€58
7 May - 8 May
includes taxes & fees
6.4/10 (1,099 reviews)
Smelly room with cockrtches

Reviewed on 28 Apr 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Fully refundableReserve now, pay when you stay
The price is €112 per night from 17 May to 18 May
€112
17 May - 18 May
includes taxes & fees
8.2/10 Very Good! (1,529 reviews)
more luxurious that my usual business stays, lots of room in the suite. Breakfast was pretty ordinary, happy hour snacks were welcome

Reviewed on 29 Apr 2026

Embassy Suites by Hilton Chicago Lombard Oak Brook
See all 890 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 €1,160, 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.