Kendall County Holidays

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Your Kendall County Holiday

Lock in one of our holiday packages to Kendall County and immerse yourself in the best of this destination, starting with Oswego. From its walking trails to its many other highlights, this city is a wonderful mix of excitement and fun. A trip to Kendall County wouldn't be complete without exploring some of its most renowned cities, starting with Oswego. Some of the top attractions here include Chicago Premium Outlets and Hollywood Casino Aurora. Plano is another favourite with Kendall County travellers. Visitors to this exciting destination love Farnsworth House and Sugar Grove Family Fun Centre. Expedia has hotels, flights and all your other travel needs to help you organise your dream Kendall County holiday today.

Top Kendall County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,031, price is now £1,482 per person
£1,482
per person
5 Jul - 14 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,721 reviews)
Staff was amazing. The room was cleaned every day. Perfect spot in order to be able to explore throughout the day.

Reviewed on 20 May 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,553, price is now £1,736 per person
£1,736
per person
5 Jul - 14 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,126 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on 27 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £2,252, price is now £1,544 per person
£1,544
per person
5 Jul - 14 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
Very good Outstanding service

Reviewed on 19 May 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,344, price is now £1,648 per person
£1,648
per person
5 Jul - 14 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
The breakfast menu & service at the Lyrica was excellent. The parking was very convenient, although a little pricey at $65 for overnight. The rooms and view were simply awesome. The service at the front desk was excellent. I look forward to my next stay.

Reviewed on 20 May 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £2,266, price is now £1,626 per person
£1,626
per person
5 Jul - 14 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Lovely stay and we are at Toro right in the hotel. Fabulous dinner

Reviewed on 18 May 2026

Kendall County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
Hudson Crossing Park, Richard E Klatt Memorial Field and Cedardell Golf Club

Top hotels in Kendall County

Best Western Oswego Hotel

Best Western Oswego Hotel

2.5 out of 5
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is £71 per night from 21 Jun to 22 Jun
£71
21 Jun - 22 Jun
includes taxes & fees
8.8/10 Excellent! (907 reviews)
"Would definitely stay here again."

Reviewed on 20 May 2026

Best Western Oswego Hotel
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 £76 per night from 3 Jun to 4 Jun
£76
3 Jun - 4 Jun
includes taxes & fees
9/10 Wonderful! (2,742 reviews)
"Everything was good but my room was a little small."

Reviewed on 20 May 2026

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 £67 per night from 25 May to 26 May
£67
25 May - 26 May
includes taxes & fees
7.2/10 Good! (1,573 reviews)
"Stayed Friday-Monday in a room with a hot tub. The jets in the hot tub are extremely forceful. Water pressure strong in bathroom as well. Fridge and microwave good. Only one electric outlet near the bed. Kept hitting the metal frame of the bed when i got in and out of it which was annoying. Ice machine ..."

Reviewed on 20 May 2026

Chicago Club Inn & Suites
See all 899 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Kendall County travel package cost?
The most affordable Kendall County travel package is £1,482, so your dream trip can become a reality — without spending an arm and a leg. Combine flights, hotels, car rentals and more to build a package that's perfect for you.
If I'm not able to travel, can I cancel my Kendall County travel package?
Don't stress if you're rethinking your Kendall County travel package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We get that life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Kendall County?
Simply by bundling. Hotels, flights and rental cars — combine whatever you need into a Kendall County travel package to save a pile of cash. Score even better deals when you include extras such as day tours to your booking. But that's not the only good part. You have the flexibility to tailor your trip your way. We offer over 550 partner airlines and 1,000,000 hotel options across the globe, so that everyone has an opportunity to travel and fulfil those holiday dreams.
Does Expedia offer Book Now, Pay Later Kendall County holidays?
We sure do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply pick the payment plan best suited to your needs during checkout and take the stress out of budgeting for your trip. Remember to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying just a small amount each month works for you, choose this option at checkout.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan from Klarna.

What are the top hotels in Kendall County?
Oswego is one place that most visitors to Kendall County put on their itinerary. For a memorable stay here, look up Holiday Inn Express & Suites Yorkville, an IHG Hotel and Hampton Inn Yorkville.
How far in advance should I book my Kendall County holiday?
Travellers are generally able to browse international flights on Expedia up to 12 months prior to departure. Booking late? With a stroke of luck, it's still possible to score a cheap ticket just weeks before your flight.
What does an Expedia Kendall County travel package include?
Rental cars, hotels and flights, or any combination of them — the choice is yours. Whether you're exploring Kendall County on a family road trip or travelling solo, there's a bundle to fit every style and budget. Once you've made your booking, why not add on one or two tours as well?
What should I know before booking a Kendall County travel package?
Find deals to match your budget with an Expedia package. Hotels, airfares, rental cars — we've got everything you need to plan your getaway. You'll save a tidy sum just by combining your bookings. Whether you're going on a snow and ski adventure or sunning yourself on a warm beach, your ideal holiday is only clicks away.
Can I choose my airline with a Kendall County Expedia travel package?
Definitely. Expedia has over 550 partner airlines to select from all over the world. With all that choice, finding the perfect carrier to bring you to Kendall County won't be difficult.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.