Kenosha County Vacation Packages

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Your Kenosha County Vacation

Head off on your next exciting adventure with a Kenosha County vacation package, and leave knowing all the details are already taken care of. And with the ability to tailor your getaway, you know it'll be one to remember. With so many things to see and do on a trip to Kenosha County, it can be hard to know where to start. Kick off your journey in Kenosha at Bristol Renaissance Faire and Simmons Island Beach — two popular attractions here. Another city worthy of a spot on your itinerary is Twin Lakes. Be sure not to miss Chain 'O Lakes State Park and Twin Lakes Private Park Beach. Start packing your suitcase, because your Kenosha County vacation is only a few clicks away with Expedia.

Top vacation destinations in Kenosha County

An aerial view of a waterfront area with a marina, buildings, and surrounding greenery.
FlightsFlightsHotelsHotels

Bristol

Bristol

Top Kenosha County Vacation 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 CA $1,389, price is now CA $921 per person
CA $921
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The room was small, but fine. The bed was comfortable. The TV was too big so it covered the thermostat control panel, and the remote Guide button didn’t work. Also, the water pressure in the shower was super weak… glad I didn’t need to wash my hair. But location, general vibe, and staff were great.

Reviewed on Jul 8, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!

Reviewed on Jul 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,047, price is now CA $1,235 per person
CA $1,235
per person
Sep 24 - Sep 28
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on Jul 8, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,110, price is now CA $1,436 per person
CA $1,436
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
I loved the suite it was so spacious and they have a 24 hour fitness center! I enjoyed my stay there.

Reviewed on Jul 8, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Great location can get a bit noisy but really nice hotel.

Reviewed on Jul 8, 2026

Kenosha County Hotel Deals

Best Western Executive Inn Kenosha/Pleasant Prairie

Best Western Executive Inn Kenosha/Pleasant Prairie

2.5 out of 5
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Jul 12 to Jul 13
CA $112
CA $135 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Best Best Western we have ever stayed in."

Reviewed on Jul 7, 2026

Best Western Executive Inn Kenosha/Pleasant Prairie
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
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul 15 to Jul 16
CA $105
CA $119 total
Jul 15 - Jul 16
includes taxes & fees
Days Inn by Wyndham Pleasant Prairie Kenosha
The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
5706 8th Ave Kenosha WI
The price is CA $165 per night from Jul 12 to Jul 13
CA $165
CA $187 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"I love The Stella due to its convenient location, history, and unique atmosphere. This is my first choice for accommodations when traveling to Kenosha. The staff was extremely friendly and accommodating. This trip involved three generations of extended family from three states. The Stella met all ..."

Reviewed on Jul 6, 2026

The Stella Hotel & Ballroom
See all 1,713 properties in Kenosha County
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.
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Frequently asked questions

How much does a Kenosha County vacation package cost?
The most affordable Kenosha County vacation package is CA $921, so your dream getaway can become a reality — without spending a fortune. Combine flights, hotels, car rentals and more to tailor make a package that suits you.
How do I get a cheap travel package to Kenosha County?
Bundle your flight and hotel bookings, add extras such as a rental car or activities, and save with a Kenosha County vacation package. You won't just score superb discounts on your escape — you'll have plenty of choice too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 properties around the globe. Your affordable vacation starts right here, right now!
What are the top hotels in Kenosha County?
When it comes to properties in Twin Lakes, Country Inn & Suites by Radisson, Kenosha, WI and Best Western Executive Inn Kenosha/Pleasant Prairie are two excellent options. If you're visiting Kenosha, The Stella Hotel & Ballroom and Wyndham Garden Kenosha Harborside will make you feel right at home.
How far in advance should I book my Kenosha County vacation?
Savvy travelers will likely want to book as early as possible. You can generally browse through international fares on Expedia up to a year before your flight. If you're booking at the last minute, don't worry. Discounted prices sometimes appear just weeks prior to departure.
What does an Expedia Kenosha County travel package include?
Hotels, flights and a reliable car for all your road trip adventures. Simply mix and match your preferred bundle and get access to incredible deals. Once you've made your booking, add on some sightseeing tours and watch your savings pile up. When it comes to crafting your Kenosha County getaway, you're the one in control!
What should I know before booking a Kenosha County travel package?
When you book your flights, hotels and car rentals together, you'll enjoy awesome discounts. Whether you're planning a beach escape in a villa or want to stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Kenosha County Expedia vacation package?
Yes, definitely. Expedia has more than 550 airline partners to select from around the globe. With such a big range of choice, finding the perfect carrier to get you to Kenosha County won't be difficult.
If I'm not able to travel, can I cancel my Kenosha County vacation package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Booked your Kenosha County vacation package in the last 24 hours? You may be able to make changes for free. For bookings made more than 24 hours ago, you may incur a fee from your airline, hotel or car rental company. For more details, visit our Customer Service Portal. We'll help you each step of the way.

Stay near popular Kenosha County attractions

A snowy field with tall grasses and a cloudy sky.

Simmons Island Beach

9.2/10 (68 reviews)
Why not spend a lazy afternoon at Simmons Island Beach during your trip to Downtown Kenosha? Stroll along the area's lakeside or simply enjoy its restaurants.
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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.