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

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Top Kenosha County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,498, price is now CA $980 per person
CA $980
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,231, price is now CA $1,411 per person
CA $1,411
per person
Aug 2 - Aug 7
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (474 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.

Reviewed on May 18, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,574, price is now CA $1,063 per person
CA $1,063
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (116 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.

Reviewed on May 17, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,801, price is now CA $1,286 per person
CA $1,286
per person
Aug 8 - Aug 12
found 23 hours ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Great location and very convenient to river walk and vicinity.

Reviewed on May 22, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,594, price is now CA $1,854 per person
CA $1,854
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Great experience! Would stay here agin

Reviewed on May 18, 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 $137 per night from May 25 to May 26
CA $137
CA $162 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"The staff was very interested in their patrons checking in…..even had chicken noodle soup being offered."

Reviewed on May 21, 2026

Best Western Executive Inn Kenosha/Pleasant Prairie
EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms

EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms

Twin Lakes WI
10/10 Exceptional! (45 reviews)
"Great property but not ideal for large groups due to extremely senstive sound monitors."

Reviewed on May 19, 2026

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EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
Doubletree by Hilton Pleasant Prairie Kenosha

Doubletree by Hilton Pleasant Prairie Kenosha

4 out of 5
11800 108th St Pleasant Prairie WI
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jun 7 to Jun 8
CA $169
CA $192 total
Jun 7 - Jun 8
includes taxes & fees
8.8/10 Excellent! (991 reviews)
"There was a nice lobby area where multiple families hung out at."

Reviewed on May 3, 2026

Doubletree by Hilton Pleasant Prairie Kenosha
See all 1,727 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 $980, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.