Kendall County Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €763, price is now €583 per person
€583
per person
21 May - 24 May
found 12 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back.

Reviewed on 4 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,054, price is now €678 per person
€678
per person
21 May - 24 May
found 12 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Comfy beds, great staff, great shower, great breakfast

Reviewed on 13 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was €870, price is now €679 per person
€679
per person
21 May - 24 May
found 12 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street

Reviewed on 12 Mar 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was €799, price is now €648 per person
€648
per person
21 May - 24 May
found 12 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,086 reviews)
Staff was extremely helpful. Rooms were clean and nearby lots of shopping and restaurants. Good continental breakfast in the morning too. Only negative was it was noisy at night with door clicking and noise when you turn on bathroom light at night. It wakes everyone with you up.

Reviewed on 13 Mar 2026

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 out of 5
Downtown Chicago
Price was €830, price is now €683 per person
€683
per person
21 May - 24 May
found 12 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (3,702 reviews)
Staff was wonderful. Room was clean. We'll definitely be visiting again!

Reviewed on 13 Mar 2026

Top hotels in Kendall County

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 €71 per night from 25 Mar to 26 Mar
€71
25 Mar - 26 Mar
includes taxes & fees
7.2/10 Good! (1,466 reviews)
The building caught fire while staying there. Every terrifying experience.

Reviewed on 9 Mar 2026

Chicago Club Inn & Suites
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 €55 per night from 27 Mar to 28 Mar
€55
27 Mar - 28 Mar
includes taxes & fees
6.4/10 (1,064 reviews)
Don't go there, it it really smell

Reviewed on 11 Mar 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
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 €125 per night from 16 Mar to 17 Mar
€125
16 Mar - 17 Mar
includes taxes & fees
8.6/10 Excellent! (1,438 reviews)
Yes, the hot tub was fine and the parking was fine too. Everything was fine.

Reviewed on 11 Mar 2026

The Champagne Lodge & Luxury Suites
See all 820 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 €583, 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.