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Oswego Vacation Packages

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Oswego Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

4 out of 5
Save 100% on your flight
Price was $450, price is now $295 per person
$295
per person
Dec 5 - Dec 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and The Glen Town Center are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,119, price is now $652 per person
$652
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The stay was all good as represented on the site!

Reviewed on Oct 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $837, price is now $500 per person
$500
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
El edificio es muy bueno, la atención del personal pésimo, siempre mal predispuestos para ayudar!

Reviewed on Oct 17, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $705, price is now $445 per person
$445
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Kenzie Hotel is a smaller hotel located close to River North and the Gold coast. Being smaller, is less people checking in / out. Evening gathering is a nice touch. Very clean

Reviewed on Oct 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $961, price is now $609 per person
$609
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $650, price is now $422 per person
$422
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The staff was 10/10.

Reviewed on Oct 15, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $866, price is now $574 per person
$574
per person
Dec 17 - Dec 20
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.

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Save 100% on your flight
Price was $990, price is now $673 per person
$673
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Ant infestation

Reviewed on Oct 16, 2026

Oswego Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

4 out of 5
Save 100% on your flight
Price was $450, price is now $295 per person
$295
per person
Dec 5 - Dec 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $816, price is now $468 per person
$468
per person
Dec 3 - Dec 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $754, price is now $487 per person
$487
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $825, price is now $545 per person
$545
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Oswego Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $927, price is now $505 per person
$505
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $907, price is now $524 per person
$524
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,119, price is now $652 per person
$652
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $876, price is now $514 per person
$514
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Alaska Airlines
Wed, Nov 18 - Thu, Nov 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Nov 18 from Los Angeles Intl. to O'Hare Intl., returning Thu, Nov 26, priced at $198 found 1 day ago
Frontier Airlines
Thu, Nov 26 - Fri, Nov 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 26 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 27, priced at $224 found 1 day ago
Southwest Airlines
Sat, Nov 14 - Tue, Nov 17
LAX
Los Angeles Intl.
MDW
Midway Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 14 from Los Angeles Intl. to Midway Intl., returning Tue, Nov 17, priced at $237 found 1 day ago
Philippine Airlines
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,102 Roundtrip, found 1 hour ago
$1,102
Roundtrip
found 1 hour ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Dec 2, priced at $1,102 found 1 hour ago