
Kenosha Vacation Packages
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Your Kenosha Vacation
When a city getaway is calling, answer it with a Kenosha vacation package. The neighborhood of Downtown Kenosha, which is great for history, shopping and culture, makes a great base for your adventures. Fill your free time with tours of Carthage College, Simmons Island Beach and Kenosha Public Museum, some of the things you just have to see during a trip to Kenosha. Whoever you're taking time off with and whatever you plan to spend, your dream Kenosha vacation is just a few clicks away with Expedia.
Top Kenosha Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,536, price is now CA $1,040 per person
CA $1,040
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
The front foyer had beautiful glass bulbs that were very dusty and dirty. Not a good first impression
Housekeeping or room service could have been disclosed for 4 nights garbage build up Also notice we had no bathroom hooks to hang wet towels just one towel bar.
Bed was comfortable and linens were fine.
Oh and, $8 bottle of Voss water in room no cups in room or bathroom. Microwave breakfast 😑
Reviewed on Jun 15, 2026

Pendry Chicago
Downtown Chicago
Price was CA $1,838, price is now CA $1,230 per person
CA $1,230
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Beautiful hotel. Very clean which is very important to me. Couldn’t have asked for a more perfect location. Food and drink prices at the restaurant/bar were high. Other than that, would highly recommend.
Reviewed on Jun 16, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,943, price is now CA $1,367 per person
CA $1,367
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun
Reviewed on Jun 17, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,961, price is now CA $1,396 per person
CA $1,396
per person
Sep 2 - Sep 6
found 22 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026

The Pfister Hotel
Downtown Milwaukee
Price was CA $1,611, price is now CA $1,164 per person
CA $1,164
per person
Aug 29 - Aug 31
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,134 reviews)
Beautiful, historic hotel in downtown Milwaukee. Excellent location, allowing us to walk to various attractions. The staff was always friendly and helpful.
Reviewed on Jun 17, 2026
Kenosha Hotel Deals

The Stella Hotel & Ballroom
5706 8th Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jun 21 to Jun 22
CA $150
CA $170 total
Jun 21 - Jun 22
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"This hotel in an historic building is completely modern and beautifully decorated. We particularly enjoyed the front patio and ice cream store across the street. Perfect location if you want to visit the museums and walk downtown."
Reviewed on Jun 16, 2026

Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Jun 21 to Jun 22
CA $116
CA $139 total
Jun 21 - Jun 22
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Very dusty and not well cleaned. Pool key was useless when the door is unlocked. Hotel door kept popping open if we didnt use the other locks to prevent it. Breakfast tasted 2 days old."
Reviewed on Jun 16, 2026

Wyndham Garden Kenosha Harborside
5125 6th Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Jul 1 to Jul 2
CA $143
CA $162 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"I would not recommend this hotel. The ceiling above the shower was coming down, the towel holder in the bathroom was falling off the wall, the new flooring didn’t reach behind the toilet, a picture was removed from above the bed but the metal clips were still hanging there. And the batteries died ..."
Reviewed on Jun 17, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.











