Deals on vacations and trips to Pleasant Prairie

Save when you book Pleasant Prairie, WI package deals

Choose two or more items and save on your trip:

Pleasant Prairie flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Marriott Milwaukee Downtown

Marriott Milwaukee Downtown

4 out of 5
Downtown Milwaukee
per person
Jun 15 - Jun 17
Roundtrip flight included
New York (JFK) to Milwaukee (MKE)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A snack bar/deli, a lobby fireplace, and a library are also on offer.
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
per person
Jun 15 - Jun 17
Roundtrip flight included
New York (JFK) to Milwaukee (MKE)
This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.
Hyatt Place Milwaukee West

Hyatt Place Milwaukee West

3 out of 5
per person
Jul 29 - Aug 2
Roundtrip non-stop flight included
Mobile (MOB) to Milwaukee (MKE)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
per person
Jul 25 - Jul 28
Roundtrip non-stop flight included
Spokane (GEG) to Milwaukee (MKE)
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, dry cleaning, and luggage storage are also on offer.
Dubbel Dutch

Dubbel Dutch

3 out of 5
Downtown Milwaukee
per person
Jul 29 - Aug 2
Roundtrip non-stop flight included
Mobile (MOB) to Milwaukee (MKE)
This hotel features self parking and free WiFi in public areas. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Express check-in, express check-out, and luggage storage are also on offer.

Top Pleasant Prairie hotel deals

Days Inn by Wyndham Pleasant Prairie Kenosha

Days Inn by Wyndham Pleasant Prairie Kenosha

2.5 out of 5
7540 118th Ave, Pleasant Prairie, WI
Free Cancellation
Reserve now, pay when you stay
The price is $60 per night
$60
per night
May 12 - May 13
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
Pet friendly
Breakfast included
Doubletree by Hilton Pleasant Prairie Kenosha

Doubletree by Hilton Pleasant Prairie Kenosha

4 out of 5
11800 108th St, Pleasant Prairie, WI
Free Cancellation
Reserve now, pay when you stay
The price is $97 per night
$97
per night
May 20 - May 21
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, a snack bar/deli, and express check-in are also on offer.
Breakfast available
Pool
Super 8 by Wyndham Kenosha/Pleasant Prairie

Super 8 by Wyndham Kenosha/Pleasant Prairie

2 out of 5
7601 118th Ave, Pleasant Prairie, WI
Free Cancellation
Reserve now, pay when you stay
The price is $60 per night
$60
per night
May 5 - May 6
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Free parking, laundry facilities, and barbecue grills are also on offer.
Breakfast included
Parking included
Fairfield Inn & Suites Kenosha Pleasant Prairie

Fairfield Inn & Suites Kenosha Pleasant Prairie

2.5 out of 5
10601 120TH AVENUE, Pleasant Prairie, WI
Free Cancellation
Reserve now, pay when you stay
The price is $109 per night
$109
per night
May 15 - May 16
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Breakfast included
Pool
Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha, an IHG Hotel

Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha, an IHG Hotel

2.5 out of 5
7887 94th Ave, Pleasant Prairie, WI
Free Cancellation
The price is $88 per night
$88
per night
May 12 - May 13
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
Breakfast included
Pool
La Quinta Inn & Suites by Wyndham Chicago Gurnee

La Quinta Inn & Suites by Wyndham Chicago Gurnee

2.5 out of 5
5688 Northridge Rd, Gurnee, IL
Free Cancellation
Reserve now, pay when you stay
The price is $65 per night
$65
per night
May 7 - May 8
This hotel features an indoor pool and a spa tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Hot Tub
Pet friendly
Don't see what you're looking for?
See all available properties in Pleasant Prairie
View all properties
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

Image for Pleasant Prairie RecPlex

Pleasant Prairie RecPlex

4.5/5(47 reviews)

Catch an event at Pleasant Prairie RecPlex during your trip to Pleasant Prairie. Wander the lakeside in this family-friendly area.

Pleasant Prairie RecPlex
Image for Pleasant Prairie Premium Outlets

Pleasant Prairie Premium Outlets

4.5/5(196 reviews)

During your trip to Pleasant Prairie, you can do some window-shopping at Pleasant Prairie Premium Outlets. Wander the lakeside in this family-friendly area.

Pleasant Prairie Premium Outlets
Image for Jelly Belly Center

Jelly Belly Center

Take the family on an outing to Jelly Belly Center during your trip to Pleasant Prairie. While you're in the area, stroll along the lakeside.

Jelly Belly Center

Frequently asked questions

How much are vacation packages to Pleasant Prairie?
Splash out on a memorable travel experience in Pleasant Prairie with a vacation package starting at just $418. Organizing your tours, flights and hotels with Travelocity is easy. And even better, our packages will leave you with extra cash for loads of fun activities.
How long should my Pleasant Prairie vacation be?
There aren’t any hard and fast rules when it comes to how long your vacation in Pleasant Prairie should be, but the majority of travelers stay around 2 nights. Got some leeway with your travel dates? Consider booking a few extra nights. Then you’ll have ample time to check out the area’s hidden gems too.
Where can I get the best vacation package deals for Pleasant Prairie?
No matter how you like to travel, Travelocity can help you get your hands on the best Pleasant Prairie package deal. All you have to do is mix and match from our 400 airlines and 1,000,000 properties around the world.
Why should I purchase my Pleasant Prairie vacation package via Travelocity?
We’ve got 24/7 support, excellent service and a Price Match Guarantee. Travel is all about the journey — and we have incredible destinations for you to journey to all around the world. Travel with us and make your hip pocket happy.
Will I save money on my Pleasant Prairie car rental if I bundle it with my hotel or flight?
You most certainly can — bundle your hotel, car and flight into a Pleasant Prairie vacation package and you can save a handsome sum. With so much to see in and around Pleasant Prairie, that set of wheels will make it easy to explore. Once you’ve buckled yourself in, get out on the wide open road and make your way to Wrigley Field, an unmissable attraction about 45 mi from Pleasant Prairie.
What is the best time of year to go to Pleasant Prairie?
Head off in and spend more money on amazing experiences, rather than your hotel room. This is the most cost-effective month to book a stay. Prices are at their most expensive in , so avoid this time if you’re on a shoestring budget. April, June and July is the busiest period for Pleasant Prairie. You’ll need to book well in advance and be prepared to pay higher prices. January, February and November are the quietest months to visit.
Which airport is best for Pleasant Prairie?
For many people, a stay in Pleasant Prairie means strolling through arrivals at O’Hare Intl. Airport (ORD). This bustling airport sits 40 mi south of the downtown area. You could also opt to fly into General Mitchell Intl. Airport (MKE) (25 mi away from central Pleasant Prairie) or Midway Intl. Airport (MDW) (55 mi away from central Pleasant Prairie).
What is there to do in Pleasant Prairie?
There’s a certain kind of magic as you stroll the streets of Pleasant Prairie. Pleasant Prairie RecPlex and Pleasant Prairie Premium Outlets are just two attractions that lure visitors to this fantastic city, so add them to your to-do list.
Where should I stay when visiting Pleasant Prairie?
The Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha, an IHG Hotel is popular with many visitors. Book now before it’s too late.