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.
Pendry Chicago
Downtown Chicago
Price was CA $1,583, price is now CA $1,072 per person
CA $1,072
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,144 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,981, price is now CA $1,277 per person
CA $1,277
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,719, price is now CA $1,181 per person
CA $1,181
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too
Reviewed on May 3, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,092, price is now CA $1,458 per person
CA $1,458
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Amazing hotel and staff!
Reviewed on May 5, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,705, price is now CA $1,194 per person
CA $1,194
per person
Jun 18 - Jun 21
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 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 $142 per night from May 7 to May 8
CA $142
CA $167 total
May 7 - May 8
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
Clean and well-kept. Good value for the money
Reviewed on May 5, 2026
The Stella Hotel & Ballroom
5706 8th Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from May 14 to May 15
CA $158
CA $179 total
May 14 - May 15
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
Great place for family gatherings… food is delicious.. hotel rooms are clean, staff is warm and helpful… gathering places are warm and welcoming… Best place to stay in Kenosha!
Reviewed on May 4, 2026
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie
7011 122nd Ave Kenosha WI
Fully refundable
The price is CA $123 per night from May 10 to May 11
CA $123
CA $139 total
May 10 - May 11
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
This was our 2nd stay at this location and it was decent! they are doing a lot of remodeling and their was alot of "debree" around but overall our room was nice, clean and comfortable and there are ALOT of food options in the area. Would likely stay again.
Reviewed on May 5, 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.
