Beach Vacations in Far North Side 2026

Photo by W. Ross Wells

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Flight and Beach hotel deals in Far North Side

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

The Emily Hotel

Downtown Chicago

CA $1,459

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,335 reviews)

Lovely place in Westloop, close to everything, quiet, clean and efficient. I would stay there again.

Reviewed on Aug 20, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,477

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Four Seasons Hotel Chicago

Downtown Chicago

CA $2,256

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,001 reviews)

Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around

Reviewed on Aug 16, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,510

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (518 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,650

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,638 reviews)

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5* Beach holidays in Far North Side

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

Park Hyatt Chicago

Downtown Chicago

CA $1,856

per person

Nov 13 - Nov 17

found 24 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

9.6/10 Exceptional! (1,001 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,987

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

Very dirty

Reviewed on Aug 22, 2026

Four Seasons Hotel Chicago

Downtown Chicago

CA $2,256

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,001 reviews)

Reviewed on Aug 16, 2026

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3 Night Beach holidays in Far North Side

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

Swissotel - Chicago

Downtown Chicago

CA $1,121

per person

Oct 22 - Oct 25

just found

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,339

per person

Oct 22 - Oct 25

just found

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,449

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

Very dirty

Reviewed on Aug 22, 2026

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4 Night Beach holidays in Far North Side

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

Level Chicago Fulton Market

Downtown Chicago

CA $1,294

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (550 reviews)

Great staff and amenities. Beautiful pool, bbq area and more. Terrific room Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them. For the money your room key or a key pad should allow you in.

Reviewed on Aug 21, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,481

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,758

per person

Nov 6 - Nov 10

found 22 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

Very dirty

Reviewed on Aug 22, 2026

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What are some benefits when booking beach vacations in Far North Side?

When you travel to the beach in Far North 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 Far North 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 Far North 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 Far North Side?

There are quite a few things you can do to get cheap beach vacations in Far North Side. Prices range from CA $1,121, 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 Far North Side. These package deals let you save by booking your accommodation and your flight together with savings of up to 28.

Why should I book family beach vacations?

When you're travelling with the family to Far North 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 Far North Side?

It's easy to find a beachfront vacation accommodation in Far North 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 Far North 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 Far North 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 Far North Side

Hampton Inn Chicago North-Loyola Station

1209 West Albion Avenue Chicago IL

3 min walk from Loyola University Chicago

Stay at this hotel in Chicago. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. ...

9.4/10 Exceptional! (1,046 reviews)

"The property was very clean and the beds were super comfortable. The staff was very pleasant."

Reviewed on Aug 22, 2026

Heart O' Chicago

5990 North Ridge Ave Chicago IL

16 min walk from Loyola University Chicago

Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...

House 5863 - Chicago Bed and Breakfast

5863 North Glenwood Avenue Chicago IL

17 min walk from Loyola University Chicago

Book a stay at this business-friendly B&B in Chicago. Enjoy free breakfast, free WiFi, and a conference center. Popular attractions Wrigley Field and Lincoln ...

9.2/10 Wonderful! (515 reviews)

"The room was lovely and clean breakfast was lovely help yourself too as much as you liked"

Reviewed on Aug 19, 2026

See all 5,053 properties in Far North 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.