Southeast Wisconsin Vacation Packages
Book a Stay + Flight or Car to save on your trip
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)
Dec 2 - Dec 6
4 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $983, price is now $665 per person
$665
per person
found 1 day ago
Great stay in an elegant mostly residential building. Smooth check in, but had to fill out a few forms. Very nice staff. Young building with lots of dogs yay!
Reviewed on Sep 24, 2026
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (2,025 reviews)
Nov 28 - Dec 1
3 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,427, price is now $919 per person
$919
per person
found 1 day ago
Loved the great upgrade in room and the mini bar selection s
Reviewed on Sep 25, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,146 reviews)
Nov 26 - Nov 29
3 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Price was $968, price is now $665 per person
$665
per person
found 19 hours ago
Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.
Reviewed on Sep 23, 2026
Top rated hotels for your Southeast Wisconsin vacation package
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Free Cancellation
Reserve now, pay when you stay
16.22 mi from city center
$194 nightly
The price is $229 total per night
$229 total
Oct 25 - Oct 26
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 27 - Sep 28
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
Don't see what you're looking for?
See all available properties in Southeast Wisconsin
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.
Explore More Ways to Travel with Travelocity
- Hotels near Lotza Fun Room
- Hotels near Minooka Park
- Hotels near Fox River Park
- Cabin Rentals in New Berlin
- Condo Rentals in New Berlin
- Extended Stay Hotels in New Berlin
- Americinn Hotels in New Berlin
- Cheap Hotels in New Berlin
- Gay Friendly Hotels in New Berlin
- Hotels with Pool in New Berlin
- Hotels with Bar in New Berlin
- Hotels with Hot Tubs in New Berlin
- Hotels with an Indoor Pool in New Berlin
- Motel 6 Hotels in New Berlin
- Pet Friendly Hotels in New Berlin
- Ski Resorts & in New Berlin
- Spa Resorts & in New Berlin
- New Berlin Hotels
- Vacation Homes in New Berlin
- Villas in New Berlin
- Hotels near Infinity Fields Baseball Park
- Hotels near Waukesha County Technical College - Waukesha Campus
- Cabin Rentals in Waukesha
- Waukesha Hotels
- Motels in Waukesha
- Hotels near Carroll University
- 4 Star Hotels in Muskego
- Apartments in Muskego
- B&B in Muskego
- Cottages in Muskego
- Guest Houses in Muskego
- Hotels with Pool in Muskego
- Muskego Hotels
- Motels in Muskego
- Hotels near Moorland Road Golf Center
- Flights from Evansville to New Berlin
- Flights from Chicago to New Berlin
- Flights from Denver to New Berlin
- Flights from Houston to New Berlin
- Flights from Indianapolis to New Berlin
- Flights from Los Angeles to New Berlin
- Flights from Minneapolis - St. Paul to New Berlin
- Flights from Nashville to New Berlin
- Flights from Philadelphia to New Berlin
- Flights from Phoenix to New Berlin
- Flights from Raleigh to New Berlin
- Flights from San Antonio to New Berlin
- Flights from Seattle to New Berlin
- Flights from Sacramento to New Berlin
- Flights from Jacksonville to New Berlin
- Flights from Pittsburgh to New Berlin
- Flights from Newark to New Berlin
- Flights from Richmond to New Berlin
- Flights from Panama City to New Berlin
- Flights from Daytona Beach to New Berlin
- Flights from Manchester to New Berlin
- Flights from Medford to New Berlin
- Flights from Springfield to New Berlin
- Flights from Huntsville to New Berlin
- Flights from Colorado Springs to New Berlin
- Flights from Tampa to New Berlin
- Flights from Chicago to Waukesha
- Flights from Muskego
- Lotza Fun Room
- Frontier Airlines Center
- Shorewood Vacations
- Wisconsin State Fair Park
- New Berlin Vacations
- The Rave-Eagles Club
- Wales Vacations
- Oak Creek Vacations
- David F. Schulz Aquatic Center
- Oconomowoc Vacations
- Milwaukee County Zoo
- Milwaukee Art Museum
- Pewaukee Vacations
- Alpine Valley Ski Resort
- Mukwonago Vacations
- Menomonee Falls Vacations
- Pewaukee Lake
- Brookfield Square Mall
- Burlington Vacations
- Waukesha Vacations
- Potawatomi Bingo Casino
- Sky Trail
- Franklin Vacations
- Muskego Vacations
- Harley-Davidson Museum
- Brookfield Vacations
- Greenfield Vacations
- East Troy Vacations
- Milwaukee Vacations
- Hales Corners Vacations
