Downtown Kenosha Vacations from $215

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Your Downtown Kenosha Vacation

Book a vacation package to Downtown Kenosha and experience the best of what this lakeside neighborhood has to offer. With a reputation for history, shopping and culture, your next memorable adventure can be found right here. Want to see the sights during your trip to Downtown Kenosha? Be sure to stop by nearby attractions like Carthage College, Simmons Island Beach and Kenosha Public Museum. Expedia can help you turn your dream Downtown Kenosha vacation into reality, whatever your budget or travel plans.

The Latest Downtown Kenosha Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $416, price is now $215 per person
$215
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Everything was excellent. Will definitely stay here again. I really liked the scent of the bath/shower products and the candles in the lobby

Reviewed on Nov 20, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,175, price is now $526 per person
$526
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
Great location and staff was very accommodating. Rooms were on the small side.

Reviewed on Nov 19, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $858, price is now $463 per person
$463
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Leo handled our stay and made it seamless with first class service. Much appreciated!

Reviewed on Nov 20, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $794, price is now $443 per person
$443
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on Nov 17, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $406, price is now $227 per person
$227
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

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Downtown Kenosha Hotel Deals

The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
5706 8th Ave Kenosha WI
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from Dec 3 to Dec 4
$120 total
Dec 3 - Dec 4
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
Cool cool place.

Reviewed on Nov 14, 2025

The Stella Hotel & Ballroom
Wyndham Garden Kenosha Harborside

Wyndham Garden Kenosha Harborside

3.5 out of 5
5125 6th Ave Kenosha WI
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Dec 21 to Dec 22
$101 total
Dec 21 - Dec 22
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
Clean and comfortable place in a great location. Loved the pool and room service. Really nice and attentive staff too.

Reviewed on Nov 17, 2025

Wyndham Garden Kenosha Harborside
La Quinta Inn & Suites by Wyndham Chicago Gurnee

La Quinta Inn & Suites by Wyndham Chicago Gurnee

3 out of 5
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $69 total per night from Nov 23 to Nov 24
$69 total
Nov 23 - Nov 24
Total with taxes and fees
7.8/10 Good! (1,404 reviews)
All good.

Reviewed on Nov 15, 2025

La Quinta Inn & Suites by Wyndham Chicago Gurnee
See all 423 properties in Downtown Kenosha
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Downtown Kenosha

Visit the Kenosha Farmer's Market on Saturday and then take the amazing walk around Simmons Island Park. Beautiful! #kenosha #wisconsin #lakemichigan #sailing #beautiful

Simmons Island Beach

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.

Simmons Island Beach
Gorgeous day!

Carthage College

Explore the campus of Carthage College during your stay in Kenosha. While in this family-friendly area, you can savor the top-notch restaurants.

Carthage College

Kenosha Public Museum

You can spend an afternoon exploring the galleries in Kenosha Public Museum during your trip to Kenosha. Experience the area's live music and festivals.

Kenosha Public Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.