Book Exclusive Oswego Vacation Packages

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Oswego flight + hotel packages

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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 $1,263, price is now CA $910 per person
CA $910
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,650, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,574, price is now CA $1,063 per person
CA $1,063
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,763, price is now CA $1,252 per person
CA $1,252
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,594, price is now CA $1,854 per person
CA $1,854
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk 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 $121 per night
CA $121
CA $135 total
May 31 - Jun 1
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 $105 per night
CA $105
CA $117 total
Jun 7 - Jun 8
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 $157 per night
CA $157
CA $174 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 29 - May 30
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 $186 per night
CA $186
CA $229 total
Jun 7 - Jun 8
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.

Popular places to visit

railway trestle bridge over wallkill river valley

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

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

Keller's Farmstand

Enjoy a fun-filled day at Keller's Farmstand as part of your trip to Oswego. While in this family-friendly area, you can enjoy the restaurants.

Keller's Farmstand

Oswego Vacations

You've booked your ticket and packed your suitcase, but how familiar are you with your next memorable vacation destination? Sit back, relax and let us tell you a bit about Oswego.

You can find it 4 miles (6 kilometers) away from Montgomery and 7 miles (11 kilometers) from Yorkville.

There are around 30,000 locals that live in this part of Illinois.

Places to visit in Oswego

Have you ever wondered how master vintners turn the modest grape into a delectable bottle of wine? Visit Fox Valley Winery to see for yourself. Need more options? Hudson Crossing Park is a lush haven that's easily accessible from the main central area. After an exciting morning of exploring, chill out in one of its shady spots. But that's not all there is. The human body consists of more than 50% water. Why not return to your roots and get your hair wet at Phillips Park Family Aquatic Center?

Where do you fly into for Oswego?

Fasten your seatbelt, stow your tray table and get ready to experience Oswego! Once you land at O'Hare International Airport (ORD), the buzzing main streets will be only 30 miles (48 kilometers) southwest of here.

Frequently asked questions

How much are vacation packages to Oswego?
With deals starting at just CA $910, 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.