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 Talbott, Autograph Collection

Downtown Chicago

CA $1,060

per person

Oct 25 - Oct 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (159 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,436

per person

Oct 2 - Oct 6

found 16 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (5,106 reviews)

Love the RIU! The room was spacious, clean and the staff is very welcoming. The RIU is centrally located within the downtown area. ( This was a huge plus) Take advantage of the breakfast on the 2nd floor! Great way to start your morning and get fueled up for the day! -Highly recommend the rooftop bar, but make reservations and ask for seating on the ledge bar for the best night time view experience. (Side note; the food is bar food and not really a place to have a good meal. But the drinks are fantastic and nonalcoholic are available) Tired at the end of the day…then go to the lobby bar have a drink and sit in the lounge and relax. Highly recommended the stay!

Reviewed on Sep 1, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,193

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,003 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,368

per person

Oct 25 - Oct 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,654 reviews)

Swissotel - Chicago

Downtown Chicago

CA $1,140

per person

Oct 25 - Oct 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,577 reviews)

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5* Beach holidays in Far North Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,193

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,003 reviews)

Four Seasons Hotel Chicago

Downtown Chicago

CA $2,173

per person

Nov 6 - Nov 9

found 19 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable

Reviewed on Aug 30, 2026

The Peninsula Chicago

Downtown Chicago

CA $2,512

per person

Nov 6 - Nov 9

found 20 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.8/10 Exceptional! (1,013 reviews)

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3 Night Beach holidays in Far North Side

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

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,069

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (5,106 reviews)

Reviewed on Sep 1, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,407

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,003 reviews)

Swissotel - Chicago

Downtown Chicago

CA $1,156

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,577 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Far North Side

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4 Night Beach holidays in Far North Side

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

Swissotel - Chicago

Downtown Chicago

CA $1,381

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,577 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,436

per person

Oct 2 - Oct 6

found 16 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (5,106 reviews)

Reviewed on Sep 1, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,698

per person

Nov 4 - Nov 8

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,003 reviews)

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See all available trips from Columbus to Far North Side

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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 $1,060, 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 26.

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! (1,041 reviews)

"Everything was Ok, parking is a MESS especially if you and your kids come in the night tired and ready to sleep and have to pay either valet parking $53 per night or walk a block and park in CVS garage for less money and walk back to the hotel"

Reviewed on Aug 31, 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. ...

7.8/10 Good! (1,000 reviews)

"Clean room"

Reviewed on Aug 30, 2026

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! (517 reviews)

"Overall property and room was very clean, comfortable and enjoyable. The continental breakfast was delicious and diverse. Erick, the property owner/manager was pleasant and helpful."

Reviewed on Aug 29, 2026

See all 5,045 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.