Deals on vacations and trips to Oswego

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Oswego flight + hotel vacation 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
Save 100% on your flight
Price was $540, price is now $355 per person
$355
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A hair salon, express check-in, and express check-out are also on offer.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $483 per person
$483
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,221, price is now $763 per person
$763
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $609, price is now $383 per person
$383
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $780, price is now $498 per person
$498
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

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
$79 nightly
The price is $86 total per night
$86 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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
$75 nightly
The price is $83 total per night
$83 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the express check-out and onsite conference space. There's an indoor pool on site, and a 24-hour front desk and a terrace are also provided.
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
$97 nightly
The price is $107 total per night
$107 total
Oct 21 - Oct 22
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Breakfast included
Parking 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
$113 nightly
The price is $125 total per night
$125 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free full breakfast each morning.
Pool
Breakfast included
Sybaris Pool Suites

Sybaris Pool Suites

2.5 out of 5
600 Ogden Ave Downers Grove IL
$155 nightly
The price is $169 total per night
$169 total
Oct 21 - Oct 22
Total with taxes and fees
Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.
Parking included
Free WiFi
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
$137 nightly
The price is $144 total per night
$144 total
Oct 28 - Oct 29
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A garden is also provided.
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

Frequently asked questions

How much are vacation packages to Oswego?
With deals starting at just $355, 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 40 mi 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 30 mi northeast of Oswego. Other options worth considering are Midway Intl. Airport (MDW) (30 mi away from central Oswego) and Rockford, IL (RFD-Greater Rockford) (50 mi 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.