Southeast Wisconsin Holidays from £1,214

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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 £1,670, price is now £1,214 per person
£1,214
per person
8 Jun - 14 Jun
found 7 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.2/10 Very Good! (2,655 reviews)
Staff was wonderful.

Reviewed on 3 May 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £7,952, price is now £5,315 per person
£5,315
per person
8 Jun - 14 Jun
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Nice and easy process

Reviewed on 29 Apr 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,462, price is now £1,684 per person
£1,684
per person
8 Jun - 14 Jun
found 7 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
A unique experience, loved being on the pier! Stunning views of the lake!

Reviewed on 2 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,954, price is now £2,049 per person
£2,049
per person
8 Jun - 14 Jun
found 7 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back

Reviewed on 27 Apr 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,352, price is now £1,661 per person
£1,661
per person
8 Jun - 14 Jun
found 7 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Loved my stayed here! It was super close to everything. We rented a car just incase but turns out we didn’t need it at all

Reviewed on 2 May 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

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 £99 per night from 4 May to 5 May
£99
4 May - 5 May
includes taxes & fees
9.2/10 Wonderful! (1,329 reviews)
Nice staff and great location! Bed not very comfortable bit otherwise the room was great.

Reviewed on 1 May 2026

Harbor Shores on Lake Geneva
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 £129 per night from 5 May to 6 May
£129
5 May - 6 May
includes taxes & fees
9.2/10 Wonderful! (1,445 reviews)
Such a great spot, the rooms were clean & spacious. The casino is so big & the staff were all so helpful!

Reviewed on 2 May 2026

Potawatomi Hotel & Casino
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
500 W Florida Street Milwaukee WI
The price is £124 per night from 24 May to 25 May
£124
24 May - 25 May
includes taxes & fees
9.2/10 Wonderful! (1,090 reviews)
Easy to get to. Clean. Nice room.

Reviewed on 3 May 2026

The Iron Horse Hotel
See all 2,440 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

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 top-notch restaurants 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.