Search Deals onSouthwest Wisconsin Vacation Packages
Southwest Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
Save 100% on your flight
Price was $686, price is now $460 per person
$460
per person
Jun 23 - Jun 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $773, price is now $472 per person
$472
per person
May 8 - May 11
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.
Fairmont Chicago at Millennium Park
Save 100% on your flight
Price was $835, price is now $533 per person
$533
per person
Jun 12 - Jun 15
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 full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Save 100% on your flight
Price was $786, price is now $548 per person
$548
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
Hilton Garden Inn Chicago Downtown South Loop
Save 100% on your flight
Price was $801, price is now $560 per person
$560
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Level Chicago – Old Town
Save 100% on your flight
Price was $817, price is now $586 per person
$586
per person
May 1 - May 4
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,325, price is now $952 per person
$952
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Sand Hill On The Lake
Price was $769, price is now $556 per person
$556
per person
May 23 - May 27
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and a private beach. Popular attractions Geneva National Golf Club and Lake Como 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, Apr 9 - Mon, Apr 13
BOS
Logan Intl.
RFD
Greater Rockford
$208 Roundtrip, found 1 day ago
$208
Roundtrip
found 1 day ago
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$228 Roundtrip, found 17 hours ago
$228
Roundtrip
found 17 hours ago
Tue, Jun 9 - Tue, Jun 16
DEN
Denver Intl.
MSN
Dane County Regional
$244 Roundtrip, found 4 hours ago
$244
Roundtrip
found 4 hours ago
Thu, Apr 30 - Sun, May 3
MSP
Minneapolis - St. Paul Intl.
RFD
Greater Rockford
$248 Roundtrip, found 4 hours ago
$248
Roundtrip
found 4 hours ago
Discover Other Travel Deals
- Popular Vacation Attractions
- Popular Destinations
- Nearby Destinations
- Areas of Southwest Wisconsin
- Hotwire Picks
- University of Wisconsin-Madison Vacations
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- Ho-Chunk Casino Vacations
- The House on the Rock Vacations
- University of Wisconsin Hospital and Clinics Vacations
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- La Crosse Center Vacations
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