Kenosha Vacations from SAR5,197

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The Latest Kenosha Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Aug 14 - Aug 19
found 1 day ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
9.2/10 Wonderful! (1,754 reviews)
Our stay was ok. The hotel was not as updated as the pictures on the site shows. The carpets were stained and worn down, and the sheets and rooms were very old and outdated. The rooftop looked nothing like the photos. Otherwise it’s in a great location.

Reviewed on 31 May 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug 14 - Aug 19
found 1 day ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
9.4/10 Exceptional! (1,598 reviews)
The property was in a great location and is beautiful. It was clean and well maintained. We had a few issues with a breakfast buffet. I highly recommend ordering from the menu instead. Also, with amenities in the room. The staff were quick to fix the issues and to make things right.

Reviewed on 4 June 2025

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
per person
Aug 14 - Aug 19
found 1 day ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
10/10 Exceptional! (1 review)
Perfect location. The roads are very clean and most importantly the mattress was very comfortable. We had the option to use a non pet friendly rooms since I have allergies and got a room higher floor for a free upgrade. So far one of the best hotels I’ve ever stayed at.

Reviewed on 24 May 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Aug 14 - Aug 19
found 1 day ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
9/10 Wonderful! (315 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on 1 June 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Aug 14 - Aug 19
found 1 day ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Attention to details. Housekeeping is stellar.

Reviewed on 31 May 2025

Find the Best Kenosha Vacation Packages

Frequently asked questions

How much does a Kenosha vacation package cost?
You can snap up a vacation package to this popular destination from SAR5,197 on Expedia. But how much your vacation to Kenosha costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Kenosha?
December, January and February are the best times to search for cheap Kenosha vacation packages. Traveling in less busy periods means you’ll typically find better prices on flights and hotels.
How to find the best Kenosha package deals?
Use Expedia’s handy filters to help you find some tempting Kenosha package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or look for Kenosha package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it’s typically best to book your vacation package well in advance.
Is it cheaper to book a Kenosha vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can tailor your Kenosha trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Kenosha?
If you’re planning an impromptu Kenosha vacation, check out our last-minute deals that can be booked up to one week before you take off. Don’t want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Kenosha?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Kenosha.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and airfares. Your hotel will likely be the biggest expense during your trip to Kenosha.
  3. Decide how long to go away for: Now that you know more about Kenosha, you can work out the perfect length of your break. Create a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: Once you’ve nailed down your travel dates and duration, book the perfect Kenosha vacation package for you.

Discover the most popular places to visit in Kenosha

Gorgeous day!

Carthage College

4.5/5(38 reviews)

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
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

University of Wisconsin-Parkside

Walk around the campus at University of Wisconsin-Parkside as part of your travels around Kenosha. While in this family-friendly area, you can savor the top-notch restaurants.

University of Wisconsin-Parkside