Southeast Wisconsin Vacation Packages
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Your Southeast Wisconsin Vacation
Our Southeast Wisconsin vacation packages provide an affordable, easy and immersive way to enjoy everything this exciting destination has to offer. If it's distilleries and craft breweries and dining you're yearning for, this is the place to come. With so many things to see and do on a trip to Southeast Wisconsin, it can be tricky to know where to begin. Kick off your journey in Milwaukee at American Family Field and Wisconsin State Fair Park — two much-loved attractions here. Another top city worth adding to your itinerary is Lake Geneva. Be sure not to miss Geneva Lake and Walworth County Fairgrounds. Expedia has everything you need for planning your Southeast Wisconsin vacation. From accommodations and flights, to car rentals and activities, we know how to curate a travel experience like no other.
Top Southeast Wisconsin Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,612, price is now CA $1,124 per person
CA $1,124
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
I thoroughly enjoyed my stay at Hotel Felix! While it may not technically be a five-star luxury chain, it definitely gave us five-star hotel vibes thanks to the incredible staff and the fantastic extra perks.The location is absolutely awesome. It puts you about a mile or so from all the major hotspots, including Navy Pier, the Riverwalk, and the Magnificent Mile. There are tons of excellent places to eat right nearby, and having a Divvy bike rental station right down the street made exploring the city incredibly easy.The service from the staff was top-notch from start to finish. I highly recommend this hotel for anyone looking for a stylish, perfectly located, and highly accommodating place to stay in Chicago!
Reviewed on Jul 13, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,847, price is now CA $1,343 per person
CA $1,343
per person
Oct 6 - Oct 9
found 3 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,595, price is now CA $1,178 per person
CA $1,178
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Booked this stay for my husband Birthday. Wanted to make sure he enjoyed himself as well as me. I spent over $800 for the corner room, check in is at 4pm and we arrived about 430ish. Got to the room and the Amenities I purchased wasn’t there which was $100(they stated it would be at 4pm) which is why I want to arrive later. I noticed that the bed sheets were ripped, small stains on the couch in front of bed and the seat in the corner by the window that creeped me out. So we left and via Hilton app I contacted the Hotel to find out why my paid Amenities wasn’t there and they sat them in there while we were gone to dinner. We got back and the chocolate covered strawberries were melted. The best part about the stay was the firework show. My husband and I enjoyed ourselves as best we could after noticing these issues it was disgusting seeing the stains and the ripped sheets especially paying what was over $1000 for one night
Reviewed on Jul 13, 2026
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.
Southeast Wisconsin Hotel Deals
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Jul 20 to Jul 21
CA $253
CA $319 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,375 reviews)
"The property is clean and well run. Staff very nice and helpful. The view of Lake Geneva from our room balcony is beautiful and hard to beat!"
Reviewed on Jul 12, 2026
Potawatomi Hotel & Casino
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jul 15 to Jul 16
CA $223
CA $263 total
Jul 15 - Jul 16
includes taxes & fees
9.2/10 Wonderful! (1,656 reviews)
"Room was nice, did stay 2 nights they gave us a room with a attached door..and had to listen to screaming kids for 2 nights called down and staff was not very helpful just sent up security second night went to desk manager still didn't help.said they over booked and could not gets us a new room. ..."
Reviewed on Jul 12, 2026
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Jul 27 to Jul 28
CA $273
CA $322 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (2,172 reviews)
"."
Reviewed on Jul 12, 2026
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.
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- Burke Vacations
- Milwaukee Vacations
- Bristol Vacations
- Wind Point Lighthouse
- Silver Lake Vacations
- Discovery World
- Visit Pewaukee
- Brookfield Square Mall
- Mitchell Park Horticultural Conservatory
- Lake Geneva Vacations
- Basilica of Saint Josaphat
- Whitewater Vacations
- Moose Mountain Falls Waterpark
- Visit Washington Heights
- Milwaukee City Hall
- Visit Johnson Woods
- Belgium Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
