Skip to main content
A pond surrounded by grass and trees, with a wooden bridge in the background.

Pleasant Prairie Vacations from $543

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Pleasant Prairie Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Daily cooked-to-order breakfast for a fee
    Sep 25 - Sep 28

    Lake Lawn Resort + Flight

    Delavan
    3 nights
    3.5 star property
    9.2/10 - Wonderful (1,000 reviews)
    "Room was fine but family above us was noisy, stomping, jumping the whole time except from midnight-7 even after we called to notify the front desk. Hot tub closed just before we wanted to use it. Employees were not particularly helpful or friendly except at checkout. Buildings are old and walls/ceilings are thin. Air conditioning was so noisy that we turned it off so we could sleep. Food at the restaurant was good but not exceptional. Will stay somewhere else if we go to Lake Geneva again."
    Reviewed July 15, 2026
    Roundtrip • Houston (IAH) - Milwaukee (MKE)
    IAH - ORD • Nonstop ORD - IAH • Nonstop
    $674
    $543
    per traveler
    found 1 day ago
    Lake Lawn Resort
  • Lobby
    Sep 27 - Sep 30

    The Pfister Hotel + Flight

    Downtown Milwaukee
    3 nights
    4.5 star property
    9.6/10 - Exceptional (2,154 reviews)
    "We were in Milwaukee for our son’s engagement. I had scheduled some special deserts to be shipped from NewJersey. I had called the hotel and advised them to refrigerate the box immediately when received. I was assured that they would take care of it. However when we arrived, and were ready to leave for the engagement we were informed that they had put the box in the freezer instead of the refrigerator. Also the management did not make any attempt to apologize for messing this up for us...."
    Reviewed July 14, 2026
    Roundtrip • New York (JFK) - Milwaukee (MKE)
    JFK - MKE • Nonstop MKE - JFK • Nonstop
    $1,464
    $985
    per traveler
    found 1 day ago
    The Pfister Hotel
  • 2 restaurants; lunch and dinner served
    Sep 27 - Sep 30

    The Iron Horse Hotel + Flight

    Fifth Ward
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,214 reviews)
    Roundtrip • New York (JFK) - Milwaukee (MKE)
    JFK - MKE • Nonstop MKE - JFK • Nonstop
    $1,177
    $893
    per traveler
    found 1 day ago
    The Iron Horse Hotel
  • Exterior
    Aug 18 - Aug 24

    Holiday Inn Express Milwaukee Downtown by IHG + Flight

    Downtown Milwaukee
    6 nights
    2.5 star property
    9.0/10 - Wonderful (1,016 reviews)
    "Great stay….perfect for summerfest"
    Reviewed July 13, 2026
    Roundtrip • Austin (AUS) - Milwaukee (MKE)
    AUS - ORD • 1 stop ORD - AUS • 1 stop
    $962
    $747
    per traveler
    found 1 day ago
    Holiday Inn Express Milwaukee Downtown by IHG
  • Exterior
    Aug 18 - Aug 24

    Kinn Guesthouse Downtown + Flight

    Downtown Milwaukee
    6 nights
    4.5 star property
    9.4/10 - Exceptional (384 reviews)
    Roundtrip • Austin (AUS) - Milwaukee (MKE)
    AUS - ORD • 1 stop ORD - AUS • 1 stop
    Save 100% on your flight
    $1,094
    $860
    per traveler
    found 1 day ago
    Kinn Guesthouse Downtown

Pleasant Prairie Hotel Deals

Lobby

Days Inn by Wyndham Pleasant Prairie Kenosha

Days Inn by Wyndham Pleasant Prairie Kenosha
2.5 star property
1.3 mi from Pleasant Prairie
8.2 out of 10, Very Good, (502 reviews)
"Breakfast was typical eggs, sausage, hashbrowns, waffles, toast, nothing fancy, but free and filling. The room was clean, fridge worked, bed was comfortable. It was a basic room, included breakfast."
$71 nightly
The price is $81
Jul 20 - Jul 21
Total with taxes and fees
Days Inn by Wyndham Pleasant Prairie Kenosha
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.
See all properties in Pleasant Prairie

Frequently Asked Questions

How much does a Pleasant Prairie vacation package cost?

Offering great value package deals from $543 on Expedia, you'll be thrilled with how little a vacation to Pleasant Prairie costs! Expedia's packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Pleasant Prairie?

January, February and November are the best times to look for cheap Pleasant Prairie vacation packages. Traveling in less busy months means you can generally find reduced prices on accommodations and flights.

How many days is enough for Pleasant Prairie?

Typically, a handful of days is enough to check out the top sights during your Pleasant Prairie vacation. But if you'd like to have more time to chill out or take day trips, think about extending your trip.

Is it worth booking a vacation package to Pleasant Prairie?

Pleasant Prairie is a good vacation destination with attractions like Pleasant Prairie RecPlex among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a Pleasant Prairie vacation promises a good time for everyone.

How to find the best Pleasant Prairie package deals?

Use Expedia's filters to help you find some terrific Pleasant Prairie package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Pleasant Prairie package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.

Is it cheaper to book a Pleasant Prairie vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Pleasant Prairie vacation by choosing your favorite type of stay, airline and car class.

When to book a vacation package to Pleasant Prairie?

If you've got your Pleasant Prairie travel dates confirmed, book early to snap up some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for traveling on a whim.

Does Expedia offer Book Now, Pay Later Pleasant Prairie vacation packages?

Set off on your dream escape to Pleasant Prairie with our Book Now, Pay Later vacations. No need to scrimp and save or hold off until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up travel deals before they sell out.

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