Oswego Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Save up to ฿4,531 when you book a flight and hotel together*
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Top Oswego Flight + Hotel Deals

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

Arlo Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
There was an odd odor. My room was not ready for several hours after check in.

Reviewed on 17 Jul 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
location is unbeatable, the beddings have the smell of sweating. limited water supply, feels like in african

Reviewed on 19 Jul 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
The hotel was beautiful and historic. Not a lot of upgrades so be prepared for the classic style rooms.

Reviewed on 19 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Comfortable beds and nice breakfast. Close to parking. Recommend.

Reviewed on 19 Jul 2025

Top hotels in Oswego

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 ฿2,695 per night from 27 Jul to 28 Jul
฿2,695
฿2,991 total
27 Jul - 28 Jul
includes taxes & fees
7.8/10 Good! (1,014 reviews)
"Clean and convenient location"

Reviewed on 18 Jul 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 ฿3,303 per night from 21 Jul to 22 Jul
฿3,303
฿3,666 total
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (2,127 reviews)
Great find for a short trip
"Nice quiet place for the night no matter where you're going after. Clean with a very friendly staff. Printer doesn't work, but there's a kinkos down the street. I recommend if you find yourself looking for a place to stay."

Reviewed on 18 Jul 2025

SureStay Plus Hotel by Best Western Chicago Lombard
Motel 6 Naperville, IL

Motel 6 Naperville, IL

2 out of 5
1585 Naperville Wheaton Road, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is ฿1,846 per night from 6 Aug to 7 Aug
฿1,846
฿2,058 total
6 Aug - 7 Aug
includes taxes & fees
7.8/10 Good! (1,030 reviews)
"Got a good deal on this room. I was weary based on the looks outside but was pleasantly surprised inside. None of the rooms have microwaves or refrigerators but that didn’t bother me. Safe was friendly and check in was quick. There was a ring type security camera outside the front door for safety. ..."

Reviewed on 14 Jul 2025

Motel 6 Naperville, IL
See all 599 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.

Frequently asked questions

How much does an Oswego holiday package cost?
You'll find cheap prices from ฿14,240 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.