Southeast Wisconsin Holidays from £1,249

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,753, price is now £1,249 per person
£1,249
per person
3 Jun - 9 Jun
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The hotel was nice , and clean. The guy at the front desk was super nice. However , the rooms are small, the shower water splashes over on to floor so extra towels are needed for the bathroom floor, and every vending machine was either jammed and or out of water.

Reviewed on 17 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,319, price is now £1,411 per person
£1,411
per person
3 Jun - 9 Jun
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
This is a great hotel. Excellent staff, cleanliness is superior and the location is perfect. I will be staying there again!

Reviewed on 18 Mar 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £2,053, price is now £1,432 per person
£1,432
per person
3 Jun - 9 Jun
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
There was no kitchen.

Reviewed on 18 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,674, price is now £1,865 per person
£1,865
per person
3 Jun - 9 Jun
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.

Reviewed on 16 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,040, price is now £1,452 per person
£1,452
per person
3 Jun - 9 Jun
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.!

Reviewed on 17 Mar 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 skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

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

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
The price is £128 per night from 29 Mar to 30 Mar
£128
29 Mar - 30 Mar
includes taxes & fees
9.6/10 Exceptional! (2,027 reviews)
My impressions of the past that the Pfister was tired hotel that expensive have been dismissed after our experience. What a gem that is affordable! Thoroughly enjoyable and looking forward to our next stay!

Reviewed on 17 Mar 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is £135 per night from 29 Mar to 30 Mar
£135
29 Mar - 30 Mar
includes taxes & fees
9.8/10 Exceptional! (2,585 reviews)
Welcoming staff with great rooms and atmosphere!

Reviewed on 17 Mar 2026

Saint Kate - The Arts Hotel
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
The price is £147 per night from 14 Apr to 15 Apr
£147
14 Apr - 15 Apr
includes taxes & fees
8.6/10 Excellent! (3,171 reviews)
Long check in line - staff was nice. Water park and rooms outdated. It was fine for 2 night but any longer than that the kids would have been bored.

Reviewed on 18 Mar 2026

Timber Ridge Lodge and Waterpark
See all 2,407 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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Popular places to visit

Harley-Davidson Museum showing interior views

Harley-Davidson Museum

4.5/5(3 reviews)

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
Ferris Wheel 11

Wisconsin State Fair Park

Enjoy an outing to Wisconsin State Fair Park during your stay in Milwaukee. Attend a sporting event or simply enjoy the top-notch restaurants 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

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. Flight-inclusive packages are ATOL protected.