Oswego Holidays

Photo by Anthony Martinez

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Oswego Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 20 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Sonesta was lovely. Easy check in. Nice room. Pillows not so great. Shuttle service was excellent as was all the staff!

Reviewed on 8 Aug, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 20 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Amazing customer service.

Reviewed on 13 Aug, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 20 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.6/10 Excellent! (2,367 reviews)
Only 1 elevator was seemingly working so it took like 10 minutes every time you wanted to use one. People in the hallways were so noisy and slamming doors at all hours and the general look and appearance of the hotel seemed worse for wear. Definitely need to invest in some major renovations and upgrades.

Reviewed on 10 Aug, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 20 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
The property does have a nice modern aesthetic and is pleasant looking. The bathroom door is a sliding door and it was difficult to open as well as it has a very chincy lock that you can tell is damaged. The photos of the outdoor patio space definitely made it appear nicer than it actually is but was still at least pleasant. Check in staff seemed a little offputting and slightly pushy to get me going when I was asking questions. Breakfast is not complimentary and is quite expensive but there are nearby options to eat still. Overall seemed a little bit overpriced for the stay.

Reviewed on 11 Aug, 2025

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 20 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,005 reviews)
Everything was perfect cool clean and respectful . Need more restaurants and fir Starbucks to close at 7 pm since there is only one restaurant to go too if don’t want to go out since we have no car

Reviewed on 11 Aug, 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$130 per night from 24 Aug to 25 Aug
S$130
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (719 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
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 S$110 per night from 31 Aug to 1 Sept
S$110
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (2,164 reviews)
"everything was good"

Reviewed on 11 Aug, 2025

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 S$97 per night from 11 Sept to 12 Sept
S$97
11 Sept - 12 Sept
includes taxes & fees
7/10 Good! (1,238 reviews)
"I liked the accessibility to the pool."

Reviewed on 9 Aug, 2025

Chicago Club Inn & Suites
See all 596 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.

Popular places to visit

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

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

Frequently asked questions

How much does an Oswego holiday package cost?
You'll find cheap prices from S$681 on Expedia for your Oswego escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your holiday to Oswego costs.
What are the cheapest months to go to Oswego?
January, February and November are the best times to look for cheap Oswego holiday packages. Opting to travel in quieter months means you can typically find better prices on flights and hotels.
How many days is enough for Oswego?
With a well-organised travel plan, you can easily tick off the most popular Oswego attractions in a few days. But if you'd like to venture off the beaten track or take day trips, think about booking your Oswego holiday for longer.
How to find the best Oswego package deals?
Start your search for an Oswego package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Oswego package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oswego adventure underway.
Is it cheaper to book an Oswego holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the freedom to create a personalised Oswego holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Oswego?
If you're planning an impromptu Oswego adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Oswego?

  1. Choose when to travel: Check your schedule and get packing. Your favourite time of year and the activities on offer will also help you decide when to escape to Oswego.
  2. Set a budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Oswego. Then, choose a property that works with your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Decide your trip length: Think about how much time you want to spend exploring Oswego. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find an Oswego holiday package that brings all your bookings together.

* 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.