Simmons Island Beach Vacation Deals: Simmons Island Beach, Downtown Kenosha Holidays

Simmons Island Beach vacation package deals

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

Ambassador Chicago, part of JdV by Hyatt

Downtown Chicago

per person

Dec. 24 - Dec. 29

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pendry Chicago

Downtown Chicago

per person

Jan. 27 - Jan. 31

found 20 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Waldorf Astoria Chicago

Downtown Chicago

per person

Dec. 29 - Jan. 1

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

Jan. 27 - Jan. 31

found 20 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Arlo Chicago

Downtown Chicago

per person

Jan. 27 - Jan. 31

found 20 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Aloft Chicago Downtown River North

Downtown Chicago

per person

Jan. 27 - Jan. 31

found 20 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Frequently asked questions

How much are vacation packages to Simmons Island Beach?

Check out Travelocity’s unbeatable CA $839 Simmons Island Beach package deal. With all the cash you save on your hotel stay and flights, you’ll be able to treat yourself to wining, dining and unforgettable local experiences. Simmons Island Beach, here you come!

Where can I get the best vacation package deals for Simmons Island Beach?

Travelocity is here to help you find a terrific Simmons Island Beach package deal. With as many as 400 partner airlines and 665,000 properties across the globe, you’re bound to find the perfect combination.

Why should I purchase my Simmons Island Beach vacation bundle with Travelocity?

Whether you’re on the hunt for the ultimate unplugged escape or after the fun and excitement of the big smoke, booking everything with Travelocity saves you time, money and hassle. No need to comb through hundreds of websites to find the best deal — our Price Match Guarantee ensures you’ll always score the lowest possible price, and our professional customer service experts are available for you round-the-clock.

Can I go on vacation to Simmons Island Beach at this time?

We have the local knowledge to ensure your vacation dreams a reality, so before booking a ticket to Simmons Island Beach, take peek at our Covid-19 Travel Advisor. This is where you can discover current info about quarantine policies, travel restrictions and a whole lot more.

Top Simmons Island Beach hotel deals

The Stella Hotel & Ballroom

5706 8th Ave, Kenosha, WI

Free cancellation

Reserve now, pay when you stay

CA $155

CA $176 total

includes taxes & fees

24 Nov - 25 Nov

Stay at this 3.5-star business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dinosaur Discovery Museum and Alpaca Art are located nearby.

Parking included

Free WiFi

Best Western Executive Inn Kenosha/Pleasant Prairie

7220 122nd Ave, Kenosha, WI

Free cancellation

Reserve now, pay when you stay

CA $101

CA $114 total

includes taxes & fees

27 Nov - 28 Nov

Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions America's Action Territory Family Fun Park and Pleasant Prairie RecPlex are located nearby.

Pool

Hot tub

Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

7011 122nd Ave, Kenosha, WI

Free cancellation

CA $112

CA $127 total

includes taxes & fees

24 Nov - 25 Nov

Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions America's Action Territory Family Fun Park and Pleasant Prairie RecPlex are located nearby.

Pool

Hot tub

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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.