Search Deals onSouthwest Wisconsin Vacation Packages
Southwest Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
Price was $405, price is now $214 per person
$214
per person
Dec 14 - Dec 17
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.

Art Villa
Save 100% on your flight
Price was $1,020, price is now $524 per person
$524
per person
Dec 31 - Jan 3
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 5-star luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $649, price is now $347 per person
$347
per person
Nov 25 - 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.

Pendry Chicago
Save 100% on your flight
Price was $918, price is now $510 per person
$510
per person
Dec 30 - Jan 4
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.

Swissotel - Chicago
Save 100% on your flight
Price was $391, price is now $220 per person
$220
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $2,182, price is now $1,274 per person
$1,274
per person
Nov 25 - Nov 30
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.

Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $561, price is now $329 per person
$329
per person
Nov 25 - 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 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
Save 100% on your flight
Price was $554, price is now $326 per person
$326
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Southwest Wisconsin Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Southwest Wisconsin 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.

Mon, Oct 20 - Mon, Oct 27
DEN
Denver Intl.
MSN
Dane County Regional
$135 Roundtrip, found 5 days ago
$135
Roundtrip
found 5 days ago

Tue, Feb 17 - Thu, Feb 19
LAS
Harry Reid Intl.
RFD
Greater Rockford
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago

Wed, Dec 3 - Sat, Dec 13
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour ago

Thu, Oct 23 - Mon, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
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