Downtown Kenosha Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 21 - Aug 24

    JW Marriott Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,001 reviews)
    "Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it."
    Reviewed May 31, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,396
    CA $1,005
    per traveller
    found 10 hours ago
    JW Marriott Chicago
  • Seasonal outdoor pool, sun loungers
    Jul 6 - Jul 10

    Hilton Grand Vacations Club Chicago Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    3.5 star property
    9.2/10 - Wonderful (396 reviews)
    "Great location and well maintained property!"
    Reviewed May 29, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,768
    CA $1,239
    per traveller
    found 7 hours ago
    Hilton Grand Vacations Club Chicago Magnificent Mile
  • Indoor wedding
    Aug 10 - Aug 14

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,362 reviews)
    "The gym is on 43 floor.. amazing"
    Reviewed May 31, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,657
    CA $1,166
    per traveller
    found 2 days ago
    Swissotel - Chicago
  • Smart TV
    Aug 10 - Aug 14

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (491 reviews)
    "Amazing place"
    Reviewed May 26, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,983
    CA $1,403
    per traveller
    found 2 days ago
    Level Chicago Fulton Market
  • Lobby lounge
    Aug 21 - Aug 24

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,002 reviews)
    "Staff was amazing and very helpful, gave us a lot of great recommendations for places to check out and also upgraded our room for free. The room was very nice, a little tight but that is expected in Chicago. Bathroom was perfect great shower, amazing view from room and bathroom window. Very conveniently located, quick walk from the train. Highly recommend and would stay again"
    Reviewed June 1, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,795
    CA $1,285
    per traveller
    found 10 hours ago
    Le Méridien Essex Chicago

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 $173 per night from Jun 3 to Jun 4
CA $173
CA $196 total
Jun 3 - Jun 4
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Charming property and super comfortable room! Loved being on the main floor!"

Reviewed on May 29, 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 $154 per night from Jun 7 to Jun 8
CA $154
CA $174 total
Jun 7 - Jun 8
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"Front desk is rude, room is so dated and the bed was horrible. The chair in the room had stains on it and so did the curtains. Broken tiles on the bathroom floor. We went to the pool which is knee deep, was over by the hot tub and there was so much scum on the side of it people had been writing bath ..."

Reviewed on May 29, 2026

Wyndham Garden Kenosha Harborside
Beach Lake Michigan King Bed Pet Friendly

Beach Lake Michigan King Bed Pet Friendly

Kenosha WI
The price is CA $214 per night from Jun 4 to Jun 5
CA $214
CA $534 total
Jun 4 - Jun 5
includes taxes & fees
9/10 Wonderful! (18 reviews)
"The property was clean and nicely appointed with all the necessities and extras. The neighborhood was quiet and walkable. Although we did not take our pet with us on this trip, we were pleased to know that it was an option. The owners were very responsive and friendly with messaging. Highly recommend ..."

Reviewed on Apr 13, 2026

Beach Lake Michigan King Bed Pet Friendly
See all 448 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
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Family Vacations
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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 . 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.