Southeast Wisconsin Vacation Packages
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Top Southeast Wisconsin vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (573 reviews)
Nov 27 - Dec 1
4 night stay
New York (NYC) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to New York (NYC)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,059, price is now $719 per person
$719
per person
found 24 hours ago
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.
Reviewed on Sep 26, 2026
4.0-star property
The Neighborhood Hotel-Little Italy
Near West Side
9.6/10 Exceptional! (321 reviews)
Dec 3 - Dec 9
6 night stay
New York (NYC) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to New York (NYC)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,096, price is now $734 per person
$734
per person
found 1 day ago
Great studio so close to good food and easy to get around - will stay again!
Reviewed on Sep 23, 2026
4.5-star property
The Pfister Hotel
Downtown Milwaukee
9.6/10 Exceptional! (2,280 reviews)
Nov 5 - Nov 8
3 night stay
New York (JFK) to Milwaukee (MKE)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,690, price is now $1,141 per person
$1,141
per person
found 1 day ago
Everything about The Pfister is 5 stars. I would give it 10 stars if I could. The staff is amazing, the food is tasty & fresh, the hotel ambiance is perfection. This is a must-experience stay!
Reviewed on Sep 27, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (5,174 reviews)
Oct 30 - Nov 3
4 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,150, price is now $813 per person
$813
per person
found 1 day ago
4.5-star property
The Talbott, Autograph Collection
Downtown Chicago
9.4/10 Exceptional! (178 reviews)
Oct 30 - Nov 3
4 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Price was $1,042, price is now $770 per person
$770
per person
found 1 day ago
Top rated hotels for your Southeast Wisconsin vacation package
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
16.22 mi from city center
$194 nightly
The price is $229 total per night
$229 total
Oct 4 - Oct 5
Total with taxes and fees
Guests of The Pfister Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Valet parking is available for USD 46 per day. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this luxury hotel include free WiFi in public areas, meeting rooms, and a conference center.
Pool
Spa
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Free Cancellation
Reserve now, pay when you stay
6.91 mi from city center
$80 nightly
The price is $93 total per night
$93 total
Sep 28 - Sep 29
Total with taxes and fees
Guests of AmericInn by Wyndham Brookfield have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Free Cancellation
Reserve now, pay when you stay
15.86 mi from city center
$93 nightly
The price is $110 total per night
$110 total
Oct 11 - Oct 12
Total with taxes and fees
At Hyatt Regency Milwaukee, guests have access to a gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 48.56 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-in.
Pet friendly
Free WiFi
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View all propertiesLowest 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.
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