Oswego Holidays from £1,900

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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.
Best Western Plus O'Hare International South Hotel

Best Western Plus O'Hare International South Hotel

2.5 out of 5
Price was £3,295, price is now £1,900 per person
£1,900
per person
16 Aug - 20 Aug
found 13 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
7.4/10 Good! (1,008 reviews)
Quiet hotel

Reviewed on 6 Jul 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was £3,579, price is now £2,064 per person
£2,064
per person
16 Aug - 20 Aug
found 13 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,139 reviews)
Excelente hotel con una localización espectacular. Cerca de atracciones y lugares de interés. Habitaciones amplias y limpias.

Reviewed on 5 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,940, price is now £2,278 per person
£2,278
per person
17 Sept - 22 Sept
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on 2 Jul 2026

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
Price was £3,343, price is now £1,940 per person
£1,940
per person
16 Aug - 20 Aug
found 13 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
7.6/10 Good! (1,547 reviews)
Just not satisfied with anything

Reviewed on 5 Jul 2026

Motel 6 Schiller Park, IL - Chicago O'Hare

Motel 6 Schiller Park, IL - Chicago O'Hare

2 out of 5
Price was £3,289, price is now £1,910 per person
£1,910
per person
17 Aug - 22 Aug
found 15 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
6.8/10 (2,204 reviews)
Terrible

Reviewed on 5 Jul 2026

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 £71 per night from 26 Jul to 27 Jul
£71
26 Jul - 27 Jul
includes taxes & fees
8.8/10 Excellent! (961 reviews)
"Friendly front staff, clean rooms, descent breakfast options."

Reviewed on 3 Jul 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 £73 per night from 3 Aug to 4 Aug
£73
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (2,854 reviews)
"The lobby is nice I had two rooms and paid extra to have the newer rooms and not the older ones as shown in the pictures by room choice 1 room was ok partly remodeled The second room was not and had multiple things falling apart Also breakfast was always out of things and the elevator was very very ..."

Reviewed on 5 Jul 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 £58 per night from 26 Jul to 27 Jul
£58
26 Jul - 27 Jul
includes taxes & fees
7.2/10 Good! (1,629 reviews)
"Clean no bugs got pool and breakfast but som items on the breakfast were bland but definitely had a lot of options great for kids"

Reviewed on 5 Jul 2026

Chicago Club Inn & Suites
See all 562 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
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Beach Holidays
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Family Friendly Holidays

Stay near popular Oswego attractions

Hudson Crossing Park

6.0/10 (4 reviews)
A riverside sanctuary with accessible playgrounds, ziplines, and serene picnic spots along the Fox River. Explore the Egret sculpture garden or cross the pedestrian bridge for peaceful views of Waubonsie Creek.
See properties

Frequently asked questions

How much does an Oswego travel package cost?
Get set to book, because a getaway to Oswego starts from just £1,900. 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.

Explore a world of travel with Expedia

* 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.