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Oswego flight + hotel packages

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Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was CA $956, price is now CA $715 per person
CA $715
per person
Sep 11 - Sep 13
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicagoland Speedway and Route 66 Raceway are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $3,393, price is now CA $2,054 per person
CA $2,054
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,137, price is now CA $1,968 per person
CA $1,968
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,945, price is now CA $1,978 per person
CA $1,978
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,741, price is now CA $2,824 per person
CA $2,824
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Calgary (YYC) 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 $123 per night
CA $123
CA $134 total
Aug 23 - Aug 24
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 Chicago Premium Outlets and Phillips Park Family Aquatic Center are located nearby.
Pool
Breakfast included
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Free cancellation
Reserve now, pay when you stay
The price is CA $121 per night
CA $121
CA $135 total
Aug 12 - Aug 13
includes taxes & fees
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Sea Lion Aquatic Park are located nearby.
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 $84 per night
CA $84
CA $93 total
Aug 23 - Aug 24
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 Oakbrook Center Mall and Ty Warner Park are located nearby.
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 $83 per night
CA $83
CA $93 total
Aug 12 - Aug 13
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.
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 $184 per night
CA $184
CA $204 total
Aug 11 - Aug 12
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 Oakbrook Center Mall and Yorktown Shopping Center are located nearby.
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 $136 per night
CA $136
CA $151 total
Aug 18 - Aug 19
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 Oakbrook Center Mall and Yorktown Shopping Center are located nearby.
Breakfast included
Parking included
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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.

Stay near popular Oswego attractions

Hudson Crossing Park

6.0/10 (4 reviews)
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.
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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 $715, 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

A stone bridge over a calm river, surrounded by lush greenery and buildings.
A lock gate in a canal with a bridge overhead, surrounded by greenery and a small white building.