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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €643, price is now €383 per person
€383
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!

Reviewed on 26 Sept 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €881, price is now €490 per person
€490
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Nice rooms and excellent service!

Reviewed on 24 Sept 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,359, price is now €797 per person
€797
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Fantastic stay with excellent staff ! Would 100% recommend and will be returning the next time we are in Chicago.

Reviewed on 27 Sept 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €749, price is now €443 per person
€443
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
There were shops of all kinds as well as drug stores. It is located across from the Riverwalk and bridge on Michigan Avenue. In hotel restaurant and bar were good, if pricier than several nearby restaurants. The room was comfortable with a great view. I love the hotel and location. Will continue to try to stay there.

Reviewed on 27 Sept 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €850, price is now €508 per person
€508
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September. Rooms were clean modern and had loads of desk space but no dressers or nightstands. Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily. We would stay there again.

Reviewed on 26 Sept 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 €77 per night from 28 Sept to 29 Sept
€77
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (2,274 reviews)
"Nice place to stay."

Reviewed on 22 Sept 2025

SureStay Plus Hotel by Best Western Chicago Lombard
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 €99 per night from 29 Sept to 30 Sept
€99
29 Sept - 30 Sept
includes taxes & fees
8.4/10 Very Good! (1,254 reviews)
"Property was lovely"

Reviewed on 21 Sept 2025

The Champagne Lodge & Luxury Suites
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 €69 per night from 5 Oct to 6 Oct
€69
5 Oct - 6 Oct
includes taxes & fees
7/10 Good! (1,276 reviews)
"Nice and clean We really enjoy the jacuzzi we def will be back"

Reviewed on 21 Sept 2025

Chicago Club Inn & Suites
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 €383, 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.