Search Deals onSouthwest Wisconsin Vacation Packages
Southwest Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream
Save 100% on your flight
per person
Jun 20 - Jun 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this hotel in Carol Stream. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cosley Zoo and Dupage County Historical Museum are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Kimpton Gray Hotel by IHG
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Institute of Chicago and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this eco-certified 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.
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Save 100% on your flight
per person
Jun 24 - Jun 29
found 2 hours ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Odyssey Fun World and Credit Union 1 Amphitheatre are located nearby.
Congress Plaza Hotel
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
L7 Chicago by LOTTE
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this boutique 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 Chicago Riverwalk and Michigan Avenue are located nearby.
Embassy Suites by Hilton Chicago Naperville
Save 100% on your flight
per person
Jun 20 - Jun 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Nike Sports Complex 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.
Thu, Aug 28 - Sun, Aug 31
DEN
Denver Intl.
MSN
Dane County Regional
$184 Roundtrip, found 6 days ago
$184
Roundtrip
found 6 days ago
Tue, Aug 5 - Thu, Aug 14
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$204 Roundtrip, found 14 hours ago
$204
Roundtrip
found 14 hours ago
Thu, May 29 - Sun, Jun 1
MSP
Minneapolis - St. Paul Intl.
EAU
Chippewa Valley Regional
$207 Roundtrip, found 6 days ago
$207
Roundtrip
found 6 days ago
Tue, Jun 24 - Tue, Jun 24
BOS
Logan Intl.
MSN
Dane County Regional
$241 Roundtrip, found 2 days ago
$241
Roundtrip
found 2 days ago
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