Search Deals onSouthwest Wisconsin Vacation Packages
Southwest Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $566, price is now $379 per person
$379
per person
Aug 29 - Aug 31
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.
Level Chicago – Old Town
Save 100% on your flight
Price was $1,237, price is now $751 per person
$751
per person
Sep 25 - Sep 29
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.
Level hotels are awesome
Reviewed on Jul 18, 2026
Swissotel - Chicago
Save 100% on your flight
Price was $885, price is now $560 per person
$560
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,249, price is now $802 per person
$802
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!
Reviewed on Jul 17, 2026
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $1,090, price is now $717 per person
$717
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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 Michigan Avenue and Chicago Riverwalk are located nearby.
N
Reviewed on Jul 18, 2026
The Whitehall Hotel, BW Premier Collection
Save 100% on your flight
Price was $911, price is now $616 per person
$616
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Seriously outdated. No way it’s a 4-star hotel
Reviewed on Jul 18, 2026
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Save 100% on your flight
Price was $672, price is now $458 per person
$458
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Chicagoland Speedway and Route 66 Raceway are located nearby.
Level Chicago - River North
Save 100% on your flight
Price was $1,196, price is now $833 per person
$833
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. 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.
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.
Sat, Oct 10 - Sat, Oct 24
DEN
Denver Intl.
MSN
Dane County Regional
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Fri, Nov 6 - Sun, Nov 8
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$250 Roundtrip, found 19 hours ago
$250
Roundtrip
found 19 hours ago
Sat, Nov 14 - Mon, Nov 16
BOS
Logan Intl.
MSN
Dane County Regional
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Fri, Aug 14 - Tue, Aug 18
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$263 Roundtrip, found 1 day ago
$263
Roundtrip
found 1 day ago
Discover Other Travel Deals
- Popular Vacation Attractions
- Popular Destinations
- Nearby Destinations
- Areas of Southwest Wisconsin
- Hotwire Picks
- Kalahari Indoor Waterpark Vacations
- Noah's Ark Waterpark Vacations
- University of Wisconsin-Madison Vacations
- Mt. Olympus Water and Theme Park Vacations
- Chula Vista Waterparks Vacations
- Camp Randall Stadium Vacations
- Devil's Lake State Park Vacations
- The House on the Rock Vacations
- Alliant Energy Center Vacations
- Christmas Mountain Vacations
- Ho-Chunk Casino Vacations
- Capitol Square Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
