Southeast Wisconsin Holidays from AU$3,261

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Your Southeast Wisconsin Holiday

Our Southeast Wisconsin holiday 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 holiday. From accommodation and flights, to car rentals and activities, we know how to curate a travel experience like no other.

The Latest Southeast Wisconsin Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was AU$3,574, price is now AU$3,261 per person
AU$3,261
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (2,229 reviews)
Room was super clean. Awesome view and the staff was great!

Reviewed on 16 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$5,281, price is now AU$4,263 per person
AU$4,263
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on 17 Nov 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$3,863, price is now AU$3,404 per person
AU$3,404
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.

Reviewed on 18 Nov 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was AU$4,436, price is now AU$3,975 per person
AU$3,975
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
16.4/10 Exceptional! (2,158 reviews)
Not having coffee available until 6 AM (at an airport!) is just so wrong.

Reviewed on 15 Nov 2025

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was AU$3,611, price is now AU$3,276 per person
AU$3,276
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,159 reviews)
Quiet, comfortable rooms. Convenience of attractions and the staff is super friendly and helpful.

Reviewed on 18 Nov 2025

Our guide on 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
Milwaukee

Downtown Milwaukee

Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee

Southeast Wisconsin Holiday

Southeast Wisconsin Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)
Top Sights
Milwaukee County Zoo, Geneva Lake and Lake Como

Our pick of the best Southeast Wisconsin Hotel Deals

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is AU$299 per night from 19 Nov to 20 Nov
AU$299
19 Nov - 20 Nov
includes taxes & fees
8.6/10 Excellent! (3,033 reviews)
The resort was clean and fun for the whole family!

Reviewed on 14 Nov 2025

Timber Ridge Lodge and Waterpark
Hilton Milwaukee

Hilton Milwaukee

4 out of 5
509 W Wisconsin Ave Milwaukee WI
The price is AU$124 per night from 2 Dec to 3 Dec
AU$124
2 Dec - 3 Dec
includes taxes & fees
8.2/10 Very Good! (1,072 reviews)
Very nice hotel, excellent location.

Reviewed on 13 Nov 2025

Hilton Milwaukee
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 AU$240 per night from 2 Dec to 3 Dec
AU$240
2 Dec - 3 Dec
includes taxes & fees
9.4/10 Exceptional! (1,783 reviews)
Excellent, elegant hotel. Rooms were clean and luxurious, and quiet.

Reviewed on 12 Nov 2025

The Pfister Hotel
See all 2,393 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Southeast Wisconsin

Harley-Davidson Museum which includes interior views

Harley-Davidson Museum

5/5(1 review)

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.

Harley-Davidson Museum
Milwaukee County Zoo featuring zoo animals and interior views as well as a small group of people

Milwaukee County Zoo

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo

American Family Field

4.5/5(3 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.

American Family Field

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 travellers 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.