Oswego Holidays from £1,322

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    Save up to £335 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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    Rest easy

    Packages with flights are ATOL protected

Your Oswego Holiday

Our holiday 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 holiday to Oswego to suit your travel style, whatever that may be!

Top Oswego Flight + Hotel Deals

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

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,113, price is now £1,322 per person
£1,322
per person
10 Nov - 16 Nov
found 12 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,228, price is now £1,454 per person
£1,454
per person
8 Oct - 15 Oct
found 17 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,080, price is now £1,364 per person
£1,364
per person
8 Oct - 15 Oct
found 17 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
HVAC was really loud, the hallways were poorly finished. It was OK but for what we paid, we could have made a better choice.

Reviewed on 27 Aug 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,983, price is now £1,347 per person
£1,347
per person
10 Nov - 16 Nov
found 12 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,533, price is now £2,503 per person
£2,503
per person
8 Oct - 15 Oct
found 17 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Great location but a busy area

Reviewed on 25 Aug 2025

Oswego Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
34,000
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Raging Waves Waterpark, Paramount Theatre and Splash Country Waterpark

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 £75 per night from 10 Sept to 11 Sept
£75
10 Sept - 11 Sept
includes taxes & fees
8.6/10 Excellent! (723 reviews)
"Benjamin from the front desk was absolutely the best!! He was helpful, considerate, kind, always had a smile on his face and never once acted as if we were an inconvenience! The house keeping ladies were kind and friendly and always smiled!! This is by far one of the best hotels I have ever stayed ..."

Reviewed on 9 Aug 2025

Best Western Oswego Hotel
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 £68 per night from 28 Sept to 29 Sept
£68
28 Sept - 29 Sept
includes taxes & fees
7.8/10 Good! (1,102 reviews)
"Restful stay"

Reviewed on 24 Aug 2025

DoubleTree by Hilton Lisle Naperville
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 £59 per night from 16 Sept to 17 Sept
£59
16 Sept - 17 Sept
includes taxes & fees
8.8/10 Excellent! (2,198 reviews)
"We come to Illinois to visit friends and always stay here. Clean and convenient."

Reviewed on 26 Aug 2025

SureStay Plus Hotel by Best Western Chicago Lombard
See all 595 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oswego travel package cost?
Get set to book, because a getaway to Oswego starts from just £1,322. When you bundle your hotels, flights and car rentals into a travel package, you'll score the lowest prices.
If I'm not able to travel, can I cancel my Oswego travel package?
You can. We understand that things don't always go to plan, so we're here to help if you need to make changes to your Oswego travel package. You may be able to amend or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Oswego?
Book everything in one place with our Oswego travel packages. You'll discover deals on hotels, flights, tours and more that'll keep your budget happy and your sense of adventure alive. And, with more than 550 partner airlines and 1,000,000 hotels all over the world to pick from, there are endless opportunities to mix and match your own way.
Does Expedia offer Book Now, Pay Later Oswego holidays?
Yes. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply click on the payment plan best suited to your needs during checkout and take the stress out of budgeting for your next trip. Remember to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all budget sizes, so you can book that well-deserved holiday now.
  • Pay in instalments holidays: If you'd like to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan from Klarna.

Where should I stay in Oswego?
If you plan to check out Hudson Crossing Park, forget about commuting and book a hotel nearby. It's one of the top attractions in this area.
What are the top hotels in Oswego?
If it's your very first time in Oswego, make a reservation at Holiday Inn Express & Suites Yorkville, an IHG Hotel or Hampton Inn Yorkville. Both offer friendly service and are popular options with many travellers.
How far in advance should I book my Oswego holiday?
Smart travellers will likely want to book as early as possible. You can normally start comparing international fares on Expedia up to a year before your intended flight. If you're late to book, don't stress. Low prices occasionally occur in the last weeks before departure.
What does an Expedia Oswego travel package include?
Hotels, flights and car rentals — we connect you to the best deals. All you'll have to do is decide on your preferred combination. After you've made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it simple to customize an exciting Oswego holiday.
What should I know before booking an Oswego travel package?
Booking all the parts of your getaway together is a great way to save. Combine your car rentals, airfares and hotels into a tidy little package. But you're not restricted to hotels. Expedia has all kinds of properties, including holiday rentals like oceanfront condos and city residences. You've got choices galore!
Can I choose my airline with an Oswego Expedia travel package?
Most definitely. Expedia has more than 550 airline partners to select from globally. With all that choice at your fingertips, finding the perfect carrier to take you to Oswego shouldn't be hard.

* 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.