Search Deals onOswego Vacation Packages
Oswego Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Price was $639, price is now $440 per person
$440
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Price was $1,148, price is now $725 per person
$725
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 Route 66 Raceway and Harrah's Casino are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Price was $1,174, price is now $812 per person
$812
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Emily Hotel
Price was $922, price is now $649 per person
$649
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly 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 United Center and Chicago Riverwalk are located nearby.
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.
Reviewed on Nov 13, 2026
Park Hyatt Chicago
Price was $1,114, price is now $806 per person
$806
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 2026
Stay One Chicago
Price was $893, price is now $651 per person
$651
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, private pools, and 3 restaurants. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Price was $862, price is now $631 per person
$631
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
i love it
Reviewed on Nov 10, 2026
La Banque Hotel
Price was $1,184, price is now $868 per person
$868
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Very nice rooms and the hotel bar and restaurant are excellent. Variety of food and drink options within walking distance as is Amtrak and Metra access to the city.
Reviewed on Nov 12, 2026
Oswego Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Oswego Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Dec 29 - Wed, Jan 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$213 Roundtrip, found 2 hours ago
$213
Roundtrip
found 2 hours ago
Tue, Dec 29 - Wed, Jan 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$219 Roundtrip, found 2 hours ago
$219
Roundtrip
found 2 hours ago
Tue, Jan 5 - Tue, Jan 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$274 Roundtrip, found 10 hours ago
$274
Roundtrip
found 10 hours ago
Wed, Nov 18 - Mon, Nov 23
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,185 Roundtrip, just found
$1,185
Roundtrip
just found
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