Oswego Holidays

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    Save up to S$134 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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    Plan, book, and manage your trip all in one place

Oswego Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Pendry Chicago
Level Chicago – Old Town
The Emily Hotel
Arlo Chicago
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Top hotels in Oswego

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 S$160 per night from 26 Nov to 27 Nov
S$160
includes taxes & fees
26 Nov - 27 Nov
8.6/10 Excellent! (596 reviews)
"Great area, easy parking and friendly staff."

Reviewed on 23 Nov,2024

Best Western Oswego Hotel
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 S$88 per night from 2 Dec to 3 Dec
S$88
includes taxes & fees
2 Dec - 3 Dec
6.2/10 (1,000 reviews)
"VERY NICE ND CLEAN ND QUIET"

Reviewed on 18 Nov,2024

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 S$175 per night from 2 Dec to 3 Dec
S$175
includes taxes & fees
2 Dec - 3 Dec
8.4/10 Very Good! (1,011 reviews)
"The hot tub, fire place ambiance steam room. Love it"

Reviewed on 24 Nov,2024

The Champagne Lodge & Luxury Suites
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 an Oswego holiday package cost?
Get your credit card ready, because a trip to Oswego starts from just S$757. When you bundle your flights, hotels and more into a package, you’ll land great deals.
How do I get a cheap travel package to Oswego?
If you love getting an amazing deal, bundle your bookings into an Oswego holiday package. Whether you’re chasing hotels, flights, tours or rental cars, you can browse and book them all in one place. You’ll have plenty of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotels all over the world to take your pick of. Fly with who you want, stay in a place you like and save your hard-earned money — now that’s the ideal escape!
Where should I stay in Oswego?
We recommend staying near the action. Many travellers book hotels in the vicinity of top sights, such as Fox Valley Winery, Hudson Crossing Park and Kellers Farmstand.
What are the top hotels in Oswego?
When it comes to comfortable and convenient places to stay in Oswego, you can’t go past AmericInn by Wyndham Oswego. Look up its deals and pick up a great price.
How far in advance should I book my Oswego holiday?
It depends on the airline, but it’s usually possible to compare international flights on Expedia up to 12 months in advance. While it’s a good idea to book ahead of time, lucky travellers will sometimes score a cheaper seat just weeks prior to their intended journey.
What does an Expedia Oswego travel package include?
Expedia has everything you need to arrange your Oswego escape, but what goes into your package is up to you. Select from a combination of hotels, rental cars and flights. After some activities to keep you entertained? Once you’ve made your booking, you can add them too. No matter your style or budget, there’s a holiday package to match your needs.
What should I know before booking an Oswego travel package?
When you book your flights, hotels and car rentals together, you’ll land fantastic discounts. Whether you’re planning a beach escape in a villa or want to stay in an upscale city hotel, Expedia will make it happen for less.
Can I choose my airline with an Oswego Expedia holiday package?
Expedia has access to more than 550 airline partners worldwide, so you certainly can. Just pick the carrier that suits you and put together the perfect Oswego getaway.
If I'm not able to travel, can I cancel my Oswego holiday package?
Yes, it’s possible to cancel your Oswego booking if your travel plans have changed. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.