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.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,259, price is now CA $918 per person
CA $918
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable

Reviewed on Jun 23, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 16 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.

Reviewed on Jun 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,991, price is now CA $2,125 per person
CA $2,125
per person
Aug 3 - Aug 8
found 1 hour ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on Jun 25, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,313, price is now CA $936 per person
CA $936
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
Always a pleasure and a great location

Reviewed on Jun 24, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,891, price is now CA $1,359 per person
CA $1,359
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Great location, great space in the rooms!!

Reviewed on Jun 21, 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
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

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.

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Southeast Wisconsin Hotel Deals

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from Jun 30 to Jul 1
CA $224
CA $264 total
Jun 30 - Jul 1
includes taxes & fees
9.2/10 Wonderful! (1,571 reviews)
"I have stayed in two different rooms. One completely smelled like smoke. One was very, very clean. The staff is very friendly and helpful. The check-in process is extremely quick. The Asian restaurant by the elevator is absolutely incredible. The service at the rock ‘n’ roll bar especially one bartender ..."

Reviewed on Jun 26, 2026

Potawatomi Hotel & Casino
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Jun 30 to Jul 1
CA $254
CA $320 total
Jun 30 - Jul 1
includes taxes & fees
9.2/10 Wonderful! (1,342 reviews)
"They said had bar and restaurant on site. It was not open every night which was disappointing. It did not say anything about this in ad."

Reviewed on Jun 26, 2026

Harbor Shores on Lake Geneva
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $313 per night from Jul 5 to Jul 6
CA $313
CA $370 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (2,146 reviews)
"Beautiful, historic hotel. Beds and pillows were insanely comfortable. Lovely stay."

Reviewed on Jun 26, 2026

The Pfister Hotel
See all 2,446 properties in Southeast Wisconsin
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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Stay near popular Southeast Wisconsin attractions

A baseball game in a stadium with a person holding a hot dog and a drink.
Photo by Tim Ard
Open Photo by Tim Ard

American Family Field

9.0/5 (2,832 reviews)
Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.
See properties

Frequently asked questions

Can I cancel my flight booking to Southeast Wisconsin due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for most travel queries, including about flight changes related to COVID-19. For more peace of mind, read through the terms and conditions of your preferred airline before reserving your tickets.
What's the best way to find cheap flights to Southeast Wisconsin that have flexible change policies?
We know that things can change in the blink of an eye, so locking in a flexible airfare with Expedia makes good sense. Simply mark the "No change fee" box directly below the "Flexible change policies" filter. Your low-priced, flexible flight to Southeast Wisconsin is just a few clicks away.
What are some of the general tips for travelers to Southeast Wisconsin during the COVID-19 outbreak?
With strict COVID-19 precautions in effect, travel looks a lot different today. Here's what you need to know before you pack your suitcase for Southeast Wisconsin:
  • Find out if any travel restrictions apply to your destination and origin before booking anything. Also check if there are any special conditions you'll have to follow on arrival, such as proof of a negative COVID-19 test.
  • Wear a face mask even during airport screening. A TSA officer will ask you to lower your mask temporarily for identification purposes.
  • Instead of handing a TSA employee your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection.
  • You're permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. You'll need to remove it for X-ray screening.
  • Remove items from your pocket, like your phone, keys and wallet, and place them in your carry-on rather than into bins. This will minimize handling during screening.
  • If you want to take food on board, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA agent will need to touch your food container or carry-on bag for inspection.

Which airlines fly to Southeast Wisconsin?
Delta is a major carrier servicing Southeast Wisconsin. Book an airfare to General Mitchell Intl. Airport (MKE) and you'll have 573 Delta flights each month to select from.
How can I find cheap tickets to Southeast Wisconsin?
One of the easiest ways to snare cheap tickets to Southeast Wisconsin is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. You'll see the cheapest prices for nearby days. The best price for a flight to Southeast Wisconsin in the last seven days was . Booking well ahead will usually help you walk away with an even bigger bargain.
How much is a flight to Southeast Wisconsin?
One-way flights leaving () sold for as little as in the last seven days. During this period, the cost of a return airfare to Southeast Wisconsin ranged between and . If you spot a deal, book quickly — these prices don't hang about.
What are the most popular airports to fly into in Southeast Wisconsin?
General Mitchell Intl. Airport (MKE) is the main entrance point for those hoping to explore Southeast Wisconsin. Approximately 2400 flights a month touch down here.
When is the cheapest time to fly to Southeast Wisconsin?
If you can be flexible with your travel dates to Southeast Wisconsin, try to leave early in the week. The cheapest day to take off is usually Tuesday, followed by Monday. Saturday is typically the most expensive day, with a lot of people preferring to take off on the weekend.
How much is a plane ticket to Southeast Wisconsin?
Ticket prices ranged from to over the last seven days. When you're ready to book, we'll help you lock in the best price to Southeast Wisconsin.
Which airlines with flights to Southeast Wisconsin employ COVID-19 cleanliness policies?
While flying during a pandemic can be slightly overwhelming, airlines have gone above and beyond to protect the well-being of passengers and crew. These are a few carriers that have implemented changes:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.