Downtown Kenosha Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Downtown Kenosha

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,134, price is now CA $821 per person
CA $821
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,039, price is now CA $1,462 per person
CA $1,462
per person
Dec 9 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,147, price is now CA $850 per person
CA $850
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
I’ve stayed at Talbott before and enjoyed it, but this time was pretty disappointing! Towel and amenity services were awful and the shower was very poor pressure.

Reviewed on Nov 8, 2026

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Price was CA $1,638, price is now CA $1,242 per person
CA $1,242
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,106 reviews)

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was CA $1,511, price is now CA $1,166 per person
CA $1,166
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (3,188 reviews)
Elevators very slow and lots of pot smell

Reviewed on Nov 8, 2026

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
The price is CA $131 per night from Nov 10 to Nov 11
CA $131
per night
Nov 10 - Nov 11
9.2/10 Wonderful! (1,007 reviews)
"Always a great time at the Stella. Clean, convenient location & the staff is so friendly."

Reviewed on Nov 9, 2026

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
The price is CA $141 per night from Nov 24 to Nov 25
CA $141
per night
Nov 24 - Nov 25
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
The price is CA $92 per night from Nov 30 to Dec 1
CA $92
per night
Nov 30 - Dec 1
La Quinta Inn & Suites by Wyndham Chicago Gurnee
See all 449 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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Downtown Kenosha vacation package cost?
Chart your own course with our Downtown Kenosha vacation packages, which start from just CA $821. Pick the flights and hotels that match your travel style. Then, add on one or two enriching experiences for a one-of-a-kind escape.
How do I get a cheap travel package to Downtown Kenosha?
If you love amazing deals, bundle your bookings into a Downtown Kenosha vacation package. Whether you're looking for hotels, flights, activities or rental cars, you can browse and book them all in one place. You'll have a wealth of choice at your fingertips too. Expedia has more than 550 airlines and 1,000,000 properties globally to choose from. Fly with who you want, book a room where you like and save a packet — now that's the ideal getaway!
Where should I stay in Downtown Kenosha?
With so much to discover in Downtown Kenosha, it makes sense to secure a room in a hotel near its attractions. Carthage College, Simmons Island Beach and Kenosha Public Museum are some fascinating ones to put on your must-see list.
What are the top hotels in Downtown Kenosha?
If it's your first visit to Downtown Kenosha, secure a room at The Stella Hotel & Ballroom or Wyndham Garden Kenosha Harborside. Both offer friendly service and are favorites with many savvy travelers.
How far in advance should I book my Downtown Kenosha vacation?
To land rock-bottom prices, book ASAP. Air carriers usually start selling tickets, along with some of the lowest fares, around a year prior to departure. Hotels, activities and car rental should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway to Downtown Kenosha, there are always plenty of great deals to be had on Expedia. Book something in today!
What does an Expedia Downtown Kenosha travel package include?
It comes down to what you're looking for. If you're traveling alone, you might decide to bundle flights and hotels. Taking the entire family to Downtown Kenosha? A travel package including rental cars, flights and hotels might suit you better. Expedia gives you the flexibility to build your own travel package.
What should I know before booking a Downtown Kenosha travel package?
Bundling your bookings into a Downtown Kenosha vacation package is the most convenient way to organize your trip. Not only that, you'll save big just for combining your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Downtown Kenosha Expedia vacation package?
Yes, and with more than 550 airlines to pick from globally, you've got lots of choice. Take a look at the available options and find out which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Downtown Kenosha vacation package?
We understand — life sometimes gets in the way of your plans. If you've booked a Downtown Kenosha vacation package and need to amend or cancel it, we're here to help. We recommend checking out our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to cancel or amend your itinerary for free. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.

Stay near popular Downtown Kenosha attractions

A snowy field with tall grasses and a cloudy sky.

Simmons Island Beach

9.2/10 (68 reviews)
Why not spend a lazy afternoon at Simmons Island Beach during your trip to Kenosha? Stroll along the area's lakeside or simply enjoy its restaurants.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.