Downtown Kenosha Vacation Packages

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Top Holiday Package Deals in Downtown Kenosha

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Price was CA $837, price is now CA $544 per person
CA $544
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
7.6/10 Good! (1,000 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!

Reviewed on Aug. 18, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,139, price is now CA $634 per person
CA $634
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone was wonderful and the property and rooms are very well maintained. Will definitely stay there again.

Reviewed on Aug. 24, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,133, price is now CA $1,289 per person
CA $1,289
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug. 19, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,636, price is now CA $1,008 per person
CA $1,008
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,395, price is now CA $874 per person
CA $874
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
The staff were excellent

Reviewed on Aug. 21, 2025

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 $135 per night from Sep 3 to Sep 4
CA $135
CA $153 total
Sep 3 - Sep 4
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"We had a great time at this beautiful hotel!"

Reviewed on Aug. 21, 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
The price is CA $157 per night from Sep 21 to Sep 22
CA $157
CA $178 total
Sep 21 - Sep 22
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Great place to stay. Very clean and so close to so many fun activities. And the view if you stay harbor side is amazing!"

Reviewed on Aug. 21, 2025

Wyndham Garden Kenosha Harborside
Beach Lake Michigan King Bed Pet Friendly

Beach Lake Michigan King Bed Pet Friendly

Kenosha
The price is CA $190 per night from Aug 25 to Aug 26
CA $190
CA $550 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (7 reviews)
Great place by Beach
"This place was right by the beach! Very clean and comfortable"

Reviewed on Jul. 14, 2025

Beach Lake Michigan King Bed Pet Friendly
See all 382 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 $544. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.