Southeast Wisconsin Vacations from ￥253,586
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The Latest Southeast Wisconsin Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥333,620, price is now ￥253,586 per person
￥253,586
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug 29, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ￥609,956, price is now ￥430,196 per person
￥430,196
per person
Oct 6 - Oct 13
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
The best hotel for Navy Pier
Reviewed on Aug 28, 2025
Viceroy Chicago
Downtown Chicago
Price was ￥609,787, price is now ￥462,578 per person
￥462,578
per person
Oct 6 - Oct 13
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,084 reviews)
Close to everything. Gorgeous view of the lake and a beautiful rainbow. Wow!
Friendly staff.
Weird doors on the bathroom. Sliding doors tend to be noisy and unwieldy in general and this one was bad. That’s my only complaint.
Reviewed on Aug 25, 2025
The Langham, Chicago
Downtown Chicago
Price was ￥488,888, price is now ￥385,919 per person
￥385,919
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025
Where to stay in Southeast Wisconsin
Find the best Southeast Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southeast Wisconsin
Downtown Milwaukee
Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.
Find the Best Southeast Wisconsin Vacation Packages
Southeast Wisconsin Hotel Deals
Harbor Shores on Lake Geneva
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,238 reviews)
"Liked the location. Close to lake and town."
Reviewed on Aug 27, 2025
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way, Lake Geneva, WI
The price is ￥18,922 per night from Sep 23 to Sep 24
￥18,922
￥26,682 total
Sep 23 - Sep 24
includes taxes & fees
Sonesta Select Milwaukee Brookfield
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is ￥11,174 per night from Sep 18 to Sep 19
￥11,174
￥12,907 total
Sep 18 - Sep 19
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Southeast Wisconsin
Harley-Davidson Museum
4.5/5(337 reviews)
Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.
Milwaukee County Zoo
4.5/5(217 reviews)
This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.
Milwaukee Art Museum
4.5/5(400 reviews)
Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.