Beach Vacations in West Side 2026

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Flight and Beach hotel deals in West Side

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

Level Chicago – Old Town

Downtown Chicago

CA $818

per person

Oct 5 - Oct 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay. Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that. Overall a great spot. Affordable and lots of space with great views!

Reviewed on Aug 15, 2026

Swissotel - Chicago

Downtown Chicago

CA $1,132

per person

Oct 22 - Oct 25

found 5 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.

Reviewed on Aug 17, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,501

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $905

per person

Oct 28 - Oct 30

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on Aug 17, 2026

Thompson Chicago, by Hyatt

Downtown Chicago

CA $1,843

per person

Oct 11 - Oct 15

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,384 reviews)

Broken elevator causing long lines and delays. Coffee set up in the lobby was awkward and $4 for a cup. Friends found bed bug in their bed. Staff very nice and good location.

Reviewed on Aug 16, 2026

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5* Beach holidays in West Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,992

per person

Sep 28 - Oct 2

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on Aug 16, 2026

The Peninsula Chicago

Downtown Chicago

CA $2,371

per person

Oct 29 - Nov 2

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

The Langham, Chicago

Downtown Chicago

CA $2,996

per person

Sep 28 - Oct 2

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,002 reviews)

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3 Night Beach holidays in West Side

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

Swissotel - Chicago

Downtown Chicago

CA $1,132

per person

Oct 22 - Oct 25

found 5 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Reviewed on Aug 17, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,287

per person

Oct 22 - Oct 25

found 5 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on Aug 17, 2026

Pendry Chicago

Downtown Chicago

CA $1,293

per person

Sep 20 - Sep 23

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,145 reviews)

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4 Night Beach holidays in West Side

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

Swissotel - Chicago

Downtown Chicago

CA $1,322

per person

Sep 24 - Sep 28

found 10 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Reviewed on Aug 17, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,418

per person

Sep 28 - Oct 2

found 9 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

Reviewed on Aug 12, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,711

per person

Oct 11 - Oct 15

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Reviewed on Aug 15, 2026

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What are some benefits when booking beach vacations in West Side?

When you travel to the beach in West Side, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in West Side?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your West Side trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in West Side?

There are quite a few things you can do to get cheap beach vacations in West Side. Prices range from CA $818, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in West Side. These package deals let you save by booking your accommodation and your flight together with savings of up to 22.

Why should I book family beach vacations?

When you're travelling with the family to West Side, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in West Side?

It's easy to find a beachfront vacation accommodation in West Side using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and West Side as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in West Side is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Chicago. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in West Side

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL

25 min walk from United Center

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...

8.6/10 Excellent! (1,164 reviews)

"WiFi was a little bit temperamental other than that it was a great experience."

Reviewed on Aug 16, 2026

Huge 5BR Heart of Fulton Market, Duplex of dreams

Chicago IL

17 min walk from United Center

Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions United Center and Chicago Riverwalk are located ...

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Chicago IL

14 min walk from United Center

Stay at this apartment in Chicago. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions United Center and Grant Park are located ...

10/10 Exceptional! (308 reviews)

"Great location, relaxing stay in vibrant location. Intuitive supplies to make your trip enjoyable were throughout. Parking tight but a rare treat off street. Lovely decor and overall stay"

Reviewed on Aug 3, 2026

See all 805 properties in West Side

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.