Southeast Wisconsin Holidays

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Top Flight + Hotel Deals in Southeast Wisconsin

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

Arlo Chicago

4 out of 5
Downtown Chicago
Price was €674, price is now €395 per person
€395
per person
20 Nov - 25 Nov
just found
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
I wish that all the staff was more accommodating! some of them were some were not!

Reviewed on 6 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €815, price is now €456 per person
€456
per person
20 Nov - 25 Nov
just found
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on 7 Oct 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,875, price is now €1,050 per person
€1,050
per person
20 Nov - 25 Nov
just found
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on 6 Oct 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was €1,206, price is now €694 per person
€694
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,051, price is now €608 per person
€608
per person
20 Nov - 25 Nov
just found
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Perfect location and atmosphere

Reviewed on 7 Oct 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

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 €187 per night from 6 Nov to 7 Nov
€187
6 Nov - 7 Nov
includes taxes & fees
9.4/10 Exceptional! (1,762 reviews)
"Historic hotel, beautiful interior design showcasing artwork. Artist Sasha was talented, friendly and a great person to meet. Rooftop interior pool and luxe condition and quality was outstanding. Highly recommend this hotel for a first visit to Milwaukee."

Reviewed on 6 Oct 2025

The Pfister Hotel
Hilton Milwaukee

Hilton Milwaukee

4 out of 5
509 W Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is €97 per night from 2 Nov to 3 Nov
€97
2 Nov - 3 Nov
includes taxes & fees
8.2/10 Very Good! (1,052 reviews)
"Perfect"

Reviewed on 4 Oct 2025

Hilton Milwaukee
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 €149 per night from 3 Nov to 4 Nov
€149
3 Nov - 4 Nov
includes taxes & fees
9/10 Wonderful! (1,350 reviews)
"Not a drinker so I can't answer about the drinks. I did not eat breakfast at the hotel. I can't answer about the breakfast."

Reviewed on 7 Oct 2025

Potawatomi Hotel & Casino
See all 2,427 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.

Popular places to visit

Harley-Davidson Museum which includes 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
Milwaukee County Zoo which includes interior views and zoo animals 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

Fiserv Forum

Catch an event at Fiserv Forum during your trip to Milwaukee. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Fiserv Forum

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.