Pleasant Prairie Vacation Packages 2026 from $351

Pleasant Prairie flight + hotel vacation packages

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

The Ingleside Hotel

Save 100% on your flight

$351

per person

Jul 25 - Jul 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Milwaukee (MKE)

A water park and an indoor pool are featured at this traditional hotel. Traveling on business? Take advantage of the 20 conference rooms, free WiFi in public areas, and express check-out. Enjoy the gym and perks like free self parking.

The Pfister Hotel

Downtown Milwaukee

$741

per person

Jul 25 - Jul 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Milwaukee (MKE)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy the 24-hour gym.

Saint Kate - The Arts Hotel

Downtown Milwaukee

Save 100% on your flight

$883

per person

Sep 4 - Sep 7

found 17 hours ago

Roundtrip flight included

Boston (BOS) 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.

Dubbel Dutch

Downtown Milwaukee

$531

per person

Sep 4 - Sep 7

found 17 hours ago

Roundtrip flight included

Boston (BOS) 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.

The Brewhouse Inn & Suites

Westown

$713

per person

Sep 4 - Sep 7

found 17 hours ago

Roundtrip flight included

Boston (BOS) 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.

Top Pleasant Prairie hotels deals

Days Inn by Wyndham Pleasant Prairie Kenosha

7540 118th Ave Pleasant Prairie WI

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$88 total

Jun 16 - Jun 17

Total with taxes and fees

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.

Breakfast included

Pet friendly

Doubletree by Hilton Pleasant Prairie Kenosha

11800 108th St Pleasant Prairie WI

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$129 total

Jul 5 - Jul 6

Total with taxes and fees

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. There's a hot tub on site, and a 24-hour front desk and a snack bar/deli are also provided.

Pool

Hot Tub

Fairfield Inn & Suites Kenosha Pleasant Prairie

10601 120TH AVENUE Pleasant Prairie WI

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$124 total

Jul 5 - Jul 6

Total with taxes and fees

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.

Pool

Breakfast included

DoubleTree by Hilton Libertyville - Mundelein

510 E IL Route 83 Mundelein IL

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Jun 28 - Jun 29

Total with taxes and fees

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. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Pet friendly

Great Wolf Lodge Illinois

1700 Nations Dr Gurnee IL

$179 nightly

$204 total

Jun 17 - Jun 18

Total with taxes and fees

Free water park access, 5 restaurants, and 6 indoor pools are all featured at this smoke-free resort. Bring the family and enjoy the lazy river, bowling alley, and mini golf. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.

Pool

Restaurant

Hotel Indigo Chicago-Vernon Hills by IHG

450 N Milwaukee Ave Vernon Hills IL

Free Cancellation

$114 nightly

$127 total

Jul 1 - Jul 2

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and express check-in are also offered.

Pet friendly

Parking included

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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

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 Premium Outlets

4.5/5(198 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.

Frequently asked questions

How much are vacation packages to Pleasant Prairie?

Travelocity offers great package deals to Pleasant Prairie, including flights and hotels, starting from as low as $351. With all the extra money, you could book some cool tours or possibly add a few extra days to your vacation.

How long should my Pleasant Prairie vacation be?

Typically, 2 nights is what many visitors book for their Pleasant Prairie vacation. That's a good guide, but there's loads more to discover if you give yourself a few extra days.

Where can I get the best vacation package deals for Pleasant Prairie?

Travelocity is the only place you need to go to score a terrific Pleasant Prairie package deal. Take your pick of 400 airlines and 1,000,000 properties across the globe and create a vacation package that fits your style. With this amount of choice at your fingertips, you'll have plenty of inspiration for your next great escape.

Why should I book my Pleasant Prairie vacation bundle with Travelocity?

Incredible savings, countless breathtaking destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.

Will I save money on my Pleasant Prairie car rental if I book it with hotels and flights?

Bundling your hotel, car and flight into a Pleasant Prairie vacation package is an excellent way to score an amazing deal. Plus, having your own wheels gives you freedom to make your way to all those big sights you're eager to check out. Sitting 45 mi away from Pleasant Prairie, Wrigley Field is one place that should have a place on your itinerary. Top up the tank and make a day trip of it.

Which airport is best for Pleasant Prairie?

Many travelers choose to fly into O'Hare Intl. Airport (ORD), 40 mi south of downtown Pleasant Prairie. Others prefer Midway Intl. Airport (MDW) (55 mi away from central Pleasant Prairie) or General Mitchell Intl. Airport (MKE) (25 mi away from central Pleasant Prairie).

Where should I stay when visiting Pleasant Prairie?

The Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha, an IHG Hotel is recommended by many visitors. Book soon before it's too late.