Oswego Packages (Flight + Hotel)

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Top Oswego Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ฿261,909, price is now ฿237,985 per person
฿237,985
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ฿293,029, price is now ฿261,820 per person
฿261,820
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
I love Trump hotels the absolute BEST

Reviewed on 10 Jul 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ฿303,942, price is now ฿273,427 per person
฿273,427
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
The most helpful staff. The most comfortable bed. The most luxurious bathroom. The Peninsula is unrivaled amongst the five-star hotels. Cannot wait to return yet again!

Reviewed on 5 Jul 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was ฿284,210, price is now ฿257,882 per person
฿257,882
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Fantastic staff, beautiful property. Highly recommend the club lounge

Reviewed on 10 Jul 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was ฿285,807, price is now ฿264,595 per person
฿264,595
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.

Reviewed on 6 Jul 2026

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 ฿2,903 per night from 26 Jul to 27 Jul
฿2,903
฿3,164 total
26 Jul - 27 Jul
includes taxes & fees
8.8/10 Excellent! (969 reviews)
"Great breakfast, parking lot safe"

Reviewed on 6 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 ฿2,929 per night from 3 Aug to 4 Aug
฿2,929
฿3,251 total
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (2,879 reviews)
"Everything was good, as this is our 3rd or 4th time at this hotel. But this was the first time we had a first floor accommodation. And the only problem we encountered were ants crawling on the table to get to our fountain pops."

Reviewed on 11 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 ฿2,264 per night from 10 Aug to 11 Aug
฿2,264
฿2,513 total
10 Aug - 11 Aug
includes taxes & fees
7.2/10 Good! (1,646 reviews)
"Everything was good. It wasn’t any live bugs but dead ants left on top of the air conditioning unit. The corners of closet and bathroom could be more clean but it was a good stay"

Reviewed on 11 Jul 2026

Chicago Club Inn & Suites
See all 570 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.

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 holiday package cost?
You'll find cheap prices from ฿237,985 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.

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