Search Deals onSouthern Wisconsin Vacation Packages
Southern Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago
Save 100% on your flight
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Woodfield Mall are located nearby.
Staybridge Suites Chicago O'Hare - Rosemont by IHG
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Radisson Blu Aqua Hotel Chicago
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Holiday Inn Chicago O'Hare – Rosemont by IHG
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
The Hoxton Chicago
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The Peninsula Chicago
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG
Save 100% on your flight
per person
Jul 8 - Jul 10
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 Millennium Park and Art Institute of Chicago are located nearby.
Southern Wisconsin Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Southern 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.
Sat, Jul 5 - Mon, Jul 7
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$133 Roundtrip, found 2 days ago
$133
Roundtrip
found 2 days ago
Sun, Jun 15 - Sun, Jun 22
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Tue, Jul 1 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$138 Roundtrip, found 8 hours ago
$138
Roundtrip
found 8 hours ago
Sat, Jul 5 - Wed, Jul 9
MCO
Orlando Intl.
MSN
Dane County Regional
$154 Roundtrip, found 12 hours ago
$154
Roundtrip
found 12 hours ago
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