
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.


The Pfister Hotel
Downtown Milwaukee
Price was CA $1,619, price is now CA $967 per person
CA $967
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,134 reviews)
My wife and I spent a weekend at the Pfister for a wedding celebration (off property). Our room was impeccably clean and the paragon of modernity: the bathroom had more electronics than our home entertainment system! From our window on the 22nd floor we could see the lake and Summer Fest festivities. Customer service is outstanding across the entire property. The location is excellent - 3 blocks from the lake front which is fabulous. The Art Museum is fantastic! I highly recommend this property!
Reviewed on Jun 22, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,758, price is now CA $1,194 per person
CA $1,194
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.
Reviewed on Jun 20, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,439, price is now CA $1,687 per person
CA $1,687
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The people at the front desk were extremely helpful. Everyone was super kind & you never really have to leave the hotel.. plenty of shops and restaurants right there in the hotel!
Breakfast was not included, but there is breakfast on site.. there’s cheap breakfast and expensive breakfast all depends on what you are in the mood for. Wonderful stay over all!!!
Reviewed on Jun 22, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,746, price is now CA $1,217 per person
CA $1,217
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) 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
Kenosha Hotel Deals

Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jun 28 to Jun 29
CA $118
CA $141 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Check in was quick, clerk was very helpful. Room very clean and quite. Breakfast was plentiful."
Reviewed on Jun 21, 2026

The Stella Hotel & Ballroom
5706 8th Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Jul 5 to Jul 6
CA $164
CA $186 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"We used this hotel for our conference speaker to stay and he had no complaints. The front desk was very helpful in assisting me in getting the reservation and checking in my guest."
Reviewed on Jun 21, 2026

Wyndham Garden Kenosha Harborside
5125 6th Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Jun 29 to Jun 30
CA $146
CA $165 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"just thought the towel service could have been better--we never so a maid. The tv remote did not work well and so i coudl not go to the tv guide on the set--then on one of the battery runs we got a channel listing that was helpful. I could not watch the US Open because the channel access was not ..."
Reviewed on Jun 22, 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.







