Southeast Wisconsin Holidays from £1,022

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Your Southeast Wisconsin Holiday

When adventure is calling, answer it with a holiday package to Southeast Wisconsin. Kick off your journey with a visit to Milwaukee, which is known for its distilleries and craft breweries and dining. Your trip to Southeast Wisconsin wouldn't be complete without exploring some of its most renowned cities, starting with Milwaukee. A couple of the most popular attractions here include American Family Field and Wisconsin State Fair Park. Oak Creek should also be on the itineraries of all Southeast Wisconsin travellers. Visitors to this city enjoy The Rock Sports Complex and Boerner Botanical Gardens. If you're ready to stop dreaming and start discovering, Expedia will help turn your Southeast Wisconsin holiday into a reality.

Top Southeast Wisconsin Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
3 Oct - 7 Oct
found 18 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The room is clean and spacious. The river view is also beautiful especially night time. And facilities are all clean and well maintained. Good place to enjoy

Reviewed on 31 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on 30 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (229 reviews)
Room was clean, balcony had a nice view, bed were comfortable, shower was nice

Reviewed on 31 Jul 2025

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 Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)

Top hotels in Southeast Wisconsin

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
9/10 Wonderful! (1,220 reviews)
"We found the property to be in prime condition, completely renovated, although probably originally built in the 1960s. The staff was amazingly supportive and helpful. Our trip there was for seven days and we only used our car twice in that time. Perfect place for walking to the downtown!"

Reviewed on 29 Jul 2025

Get rates
Harbor Shores on Lake Geneva
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 £176 per night from 1 Sept to 2 Sept
£176
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (2,906 reviews)
"Friendly staff relaxing good time"

Reviewed on 27 Jul 2025

Timber Ridge Lodge and Waterpark
Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is £73 per night from 20 Aug to 21 Aug
£73
20 Aug - 21 Aug
includes taxes & fees
8/10 Very Good! (1,196 reviews)
"The room was well furnished, and the bed was extremely comfortable."

Reviewed on 30 Jul 2025

Sonesta Select Milwaukee Brookfield
See all 2,536 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Harley-Davidson Museum showing interior views

Harley-Davidson Museum

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

Wisconsin State Fair Park

Enjoy an outing to Wisconsin State Fair Park during your stay in West Allis. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Wisconsin State Fair Park

Mayfair Mall

You can search for that perfect souvenir at Mayfair Mall during your stay in Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Mayfair Mall

Frequently asked questions

How much does a Southeast Wisconsin travel package cost?
Discover the best of Southeast Wisconsin from as little as £1,022. We offer a great selection of hotels, flights and rental cars to suit every budget and style. You can score even better deals when you add some tours or experiences to your travel package.
If I'm not able to travel, can I cancel my Southeast Wisconsin travel package?
Because we know life can throw you a few curveballs, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.
How do I get a cheap travel package to Southeast Wisconsin?
It's as simple as bundling. Hotels, rental cars and flights — combine whatever you need into a Southeast Wisconsin travel package to save loads of cash. Score even better deals when you include extras such as tours or experiences to your booking. But that's not the only impressive part. You have the freedom to tailor your holiday your own way. We offer over 550 partner airlines and 1,000,000 properties in all corners of the globe, so that everyone has an opportunity to travel and fulfil those holiday dreams.
Does Expedia offer Book Now, Pay Later Southeast Wisconsin holidays?
Good news! We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply choose the payment plan that works for you during checkout and take away the stress of budgeting for your trip. Don't forget to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your holiday buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna can help. Paying in convenient monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

How far in advance should I book my Southeast Wisconsin holiday?
To score rock-bottom prices, book early. Airlines typically advertise flight tickets, along with some of the lowest fares, around 12 months prior to departure. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you're in need of a last-minute getaway to Southeast Wisconsin, there are always plenty of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Southeast Wisconsin travel package include?
It all comes down to what kind of trip you have in mind. Southeast Wisconsin holiday deals can include hotels, car rentals and flights. You can mix and match to find the bundle that suits your style and budget. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Southeast Wisconsin travel package?
A travel package can be easier on the credit card than individually booking all you need for your trip. For example, bundle your hotels, flights and rental cars and land a great deal. No matter your holiday plans, you're bound to find a package to suit your budget.
Can I choose my airline with a Southeast Wisconsin Expedia travel package?
Yes — that's the beauty of an Expedia package. You're in control. We have more than 550 airline partners across the globe, so you have options galore when arranging your Southeast Wisconsin adventure.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.