Book Exclusive Oswego Vacation Packages

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Oswego flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was CA $1,203, price is now CA $915 per person
CA $915
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was CA $1,371, price is now CA $1,097 per person
CA $1,097
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,146, price is now CA $924 per person
CA $924
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Chicago (ORD)
Stay at this 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.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $1,130, price is now CA $915 per person
CA $915
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $1,217, price is now CA $986 per person
CA $986
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) 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 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 $111 per night
CA $111
CA $121 total
Nov 8 - Nov 9
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 Phillips Park Family Aquatic Center and Phillips Park Zoo are located nearby.
Pool
Breakfast 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 $79 per night
CA $79
CA $87 total
Dec 2 - Dec 3
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.
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 $131 per night
CA $131
CA $145 total
Nov 3 - Nov 4
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
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
70 Yorktown Center Lombard IL
Free cancellation
Reserve now, pay when you stay
The price is CA $221 per night
CA $221
CA $245 total
Nov 22 - Nov 23
includes taxes & fees
Book a stay at this business-friendly hotel in Lombard. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Oakbrook Center Mall and Yorktown Shopping Center are located nearby.
Pool
Pet-friendly
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
Nov 29 - Nov 30
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.
Pool
Breakfast included
Sybaris Pool Suites

Sybaris Pool Suites

2.5 out of 5
600 Ogden Ave Downers Grove IL
The price is CA $197 per night
CA $197
CA $276 total
Nov 11 - Nov 12
includes taxes & fees
Stay at this hotel in Downers Grove. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Oakbrook Center Mall and Ty Warner Park are located nearby.
Parking included
Free WiFi
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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.
See properties

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 $915, 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.