Southeast Wisconsin Holidays from £793

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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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,099, price is now £793 per person
£793
per person
14 Jan - 21 Jan
found 5 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

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 £1,318, price is now £977 per person
£977
per person
21 Jan - 26 Jan
found 5 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,077, price is now £820 per person
£820
per person
2 Dec - 9 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,082, price is now £829 per person
£829
per person
14 Jan - 21 Jan
found 5 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
Everything was really nice. But we didn't have room service. And the sink had been clogged since the day we arrived.

Reviewed on 1 Nov 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,113, price is now £854 per person
£854
per person
14 Jan - 21 Jan
found 5 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)
First time staying there. The room was nice, clean and the bed was comfortable. The hotel is so conveniently located from the riverwalk, boat tours and shopping.

Reviewed on 1 Nov 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

Lake Michigan and Cathedral Square 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

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is £87 per night from 23 Nov to 24 Nov
£87
23 Nov - 24 Nov
includes taxes & fees
8.6/10 Excellent! (1,572 reviews)
"Nice"

Reviewed on 2 Nov 2026

Hyatt Regency Milwaukee
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is £75 per night from 12 Nov to 13 Nov
£75
12 Nov - 13 Nov
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

4 out of 5
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is £98 per night from 30 Nov to 1 Dec
£98
30 Nov - 1 Dec
includes taxes & fees
9.6/10 Exceptional! (2,430 reviews)
"It was nice and clean"

Reviewed on 1 Nov 2026

Drury Plaza Hotel Milwaukee Downtown
See all 2,421 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

Stay near popular Southeast Wisconsin attractions

A sign for Miller Park, home of the Milwaukee Brewers, with a baseball and stars.
Photo by trenton.badillo
Open Photo by trenton.badillo

American Family Field

9.0/10 (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

How much does a Southeast Wisconsin travel package cost?
Discover the best of Southeast Wisconsin from as little as £793. 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.

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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. Flight-inclusive packages are ATOL protected.