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Southwest Wisconsin Vacation Packages

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Southwest Wisconsin Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was $455, price is now $225 per person
$225
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Price was $1,560, price is now $624 per person
$624
per person
Dec 23 - Dec 28
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 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.
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Save 100% on your flight
Price was $559, price is now $318 per person
$318
per person
Dec 11 - Dec 16
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
Stay at this 4-star business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,001, price is now $576 per person
$576
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $926, price is now $550 per person
$550
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $882, price is now $527 per person
$527
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff 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 $441, price is now $271 per person
$271
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star eco-certified 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $670, price is now $416 per person
$416
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Southwest Wisconsin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $455, price is now $225 per person
$225
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,289, price is now $542 per person
$542
per person
Dec 23 - Dec 27
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,509, price is now $834 per person
$834
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $882, price is now $527 per person
$527
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Southwest Wisconsin Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,100, price is now $592 per person
$592
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $624 per person
$624
per person
Dec 23 - Dec 28
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,545, price is now $706 per person
$706
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,171, price is now $606 per person
$606
per person
Nov 10 - Nov 16
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.

Frontier Airlines
Mon, Oct 20 - Mon, Oct 27
DEN
Denver Intl.
MSN
Dane County Regional
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Denver Intl. to Dane County Regional, returning Mon, Oct 27, priced at $135 found 2 days ago
American Airlines
Tue, Feb 17 - Thu, Feb 19
LAS
Harry Reid Intl.
RFD
Greater Rockford
$179 Roundtrip, found 17 hours ago
$179
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Feb 17 from Harry Reid Intl. to Greater Rockford, returning Thu, Feb 19, priced at $179 found 17 hours ago
Delta
Wed, Dec 3 - Sat, Dec 13
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Dec 3 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Sat, Dec 13, priced at $199 found 2 days ago
American Airlines
Tue, Oct 28 - Sat, Nov 1
DEN
Denver Intl.
ATW
Appleton Intl.
$202 Roundtrip, found 5 days ago
$202
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Oct 28 from Denver Intl. to Appleton Intl., returning Sat, Nov 1, priced at $202 found 5 days ago