Oswego Vacation Packages

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Your Oswego Vacation

Our vacation packages to Oswego offer countless opportunities to enjoy new sights, sounds and smells. And with all of the travel arrangements taken care of, you can breathe easy and enjoy your city escape in the way that you deserve. Aurora University, Hollywood Casino Aurora and Raging Waves Waterpark are just a few of the many attractions worth checking out during your trip to Oswego. Expedia is here to help you escape your routine. Tailor your vacation to Oswego to suit your travel style, whatever that may be!

Top Oswego Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Jul. 11 - Jul. 14
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (691 reviews)
The Art Deco architectural beauty of this hotel is stunning! Every time I was in the elevator area, I was wowed. We had a corner room on the 22nd floor and it was great. Lots of space and great art deco inspired furniture and lights. We had a view of the bridge and the lake. The breakfast at the French cafe was so so. Overall I highly recommend this hotel.

Reviewed on May 30, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,200 reviews)
The spa was underwhelming. Everything else was great.

Reviewed on Jun. 1, 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 27 - Jul. 31
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (662 reviews)
Location was perfect, rooms were both efficient and cute, staff was very helpful and valet was very convenient and quick.

Reviewed on May 31, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Very friendly and helpfu

Reviewed on May 31, 2024

Oswego Hotel Deals

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 CA $149 per night from Jun. 2 to Jun. 3
CA $149
CA $162 total
includes taxes & fees
Jun 2 - Jun 3
8.6/10 Excellent! (508 reviews)
"Terrific BW. Friendly and Professional!"

Reviewed on May 28, 2024

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 CA $104 per night from Jun. 3 to Jun. 4
CA $104
CA $116 total
includes taxes & fees
Jun 3 - Jun 4
8.6/10 Excellent! (1,547 reviews)
"Simple easy check in. Pleasant staff"

Reviewed on Jun. 1, 2024

SureStay Plus Hotel by Best Western Chicago Lombard
DoubleTree by Hilton Lisle Naperville
DoubleTree by Hilton Lisle Naperville
4 out of 5
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Jun. 23 to Jun. 24
CA $120
CA $134 total
includes taxes & fees
Jun 23 - Jun 24
7.8/10 Good! (1,012 reviews)
"Everything was good"

Reviewed on May 29, 2024

DoubleTree by Hilton Lisle Naperville
See all 605 properties in Oswego
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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Oswego vacation package cost?
Get your credit card ready, because a trip to Oswego starts from just CA $778. 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 vacation 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 travelers 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 vacation?
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 travelers 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 vacation 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 vacation 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 vacation 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.

Discover the most popular places to visit in Oswego

Image for Fox Valley Winery

Fox Valley Winery

You can enjoy a tasting or tour at Fox Valley Winery during your travels to Oswego. Stroll along this family-friendly area's riverfront, or simply enjoy its breweries.

Fox Valley Winery
Image for Hudson Crossing Park

Hudson Crossing Park

Explore the great outdoors at Hudson Crossing Park, a lovely green space in Oswego. Stroll along this family-friendly area's riverfront, or simply enjoy its breweries.

Hudson Crossing Park
Image for Keller's Farmstand

Keller's Farmstand

Enjoy a fun-filled day at Keller's Farmstand as part of your trip to Oswego. While in this family-friendly area, you can enjoy the restaurants.

Keller's Farmstand

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.