Book Exclusive Oswego Vacation Packages

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Oswego flight + hotel packages

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,490, price is now CA $1,019 per person
CA $1,019
per person
Aug 6 - Aug 10
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,121, price is now CA $1,487 per person
CA $1,487
per person
Aug 19 - Aug 23
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,758, price is now CA $1,237 per person
CA $1,237
per person
Aug 6 - Aug 10
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,285, price is now CA $1,608 per person
CA $1,608
per person
Aug 18 - Aug 21
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,819, price is now CA $1,282 per person
CA $1,282
per person
Aug 6 - Aug 10
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Top Oswego hotels deals

Best Western Oswego Hotel

Best Western Oswego Hotel

2.5 out of 5
2055 Wiesbrook Dr Oswego IL
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
CA $131 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this business-friendly hotel in Oswego. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Aurora Skate Center and SciTech Hands on Museum are located nearby.
Pool
Breakfast included
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
Free cancellation
Reserve now, pay when you stay
The price is CA $117 per night
CA $117
CA $130 total
May 26 - May 27
includes taxes & fees
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Yorktown Shopping Center and Lilacia Park are located nearby.
Breakfast included
Parking included
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Free cancellation
Reserve now, pay when you stay
The price is CA $106 per night
CA $106
CA $117 total
Jun 1 - Jun 2
includes taxes & fees
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms in our reviews. Popular attractions Ty Warner Park and Mayslake Peabody Mansion are located nearby.
Pool
Breakfast included
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Free cancellation
Reserve now, pay when you stay
The price is CA $158 per night
CA $158
CA $175 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Yorktown Shopping Center and Mayslake Peabody Mansion are located nearby.
Pool
Breakfast included
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Free cancellation
Reserve now, pay when you stay
The price is CA $90 per night
CA $90
CA $101 total
May 31 - Jun 1
includes taxes & fees
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Willowbrook Community Park and Burr Ridge Village Center are located nearby.
Pet-friendly
Parking included
Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center

4 out of 5
3500 Midwest Road Oak Brook IL
Free cancellation
Reserve now, pay when you stay
The price is CA $187 per night
CA $187
CA $230 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this spa resort in Oak Brook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ty Warner Park and Mayslake Peabody Mansion are located nearby.
Pool
Spa
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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 are vacation packages to Oswego?
With deals starting at just CA $1,019, hotel and flight packages are a great way to make your travel budget stretch further. Get ready Oswego — here you come!
How long should my Oswego vacation be?
Typically, travelers spend 2 nights in Oswego. But that mightn't be enough time for you. If your aim is to discover some of the region's off-the-beaten-path treasures, why not add another couple of nights to your itinerary?
Where can I get the best vacation package deals for Oswego?
It's hard to look past Travelocity when it comes to piecing together your Oswego package deal. There are as many as 400 air carriers and 1,000,000 properties around the world to select from. Book your vacation now and get ready to tick another destination off your bucket list.
Why should I purchase my Oswego vacation bundle with Travelocity?
Travel is all about making cherished memories and forgetting all your worries — which is why we have a professional team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of vacation packages. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.
Can I save money on my Oswego car rental if I bundle it with hotels and flights?
With an Oswego vacation package, you can bundle your hotel, flight and car bookings and save a whole lot. If you're in the mood to explore the best of this awesome city, why not make a beeline for Wrigley Field? This top sight is 64 kilometers from Oswego. With your own wheels, you'll be there soon enough.
Which airport is best for Oswego?
O'Hare Intl. Airport (ORD) is popular. You'll find it roughly 48 kilometers northeast of Oswego. Other options worth considering are Midway Intl. Airport (MDW) (48 kilometers away from central Oswego) and Rockford, IL (RFD-Greater Rockford) (80 kilometers away from central Oswego).
What is there to do in Oswego?
Oswego is teeming with things to see and do, like Fox Valley Winery and Hudson Crossing Park. These two fantastic attractions top most visitors' to-do lists.
Where should I stay when visiting Oswego?
The Best Western Oswego Hotel is the top choice of many visitors. Book as soon as possible to avoid missing out.

Photos of local treasures

Browse Oswego vacation photos for more inspiration

View along the Fox River.