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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $801

per person

Nov 17 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

8.2/10 Very good! (3,012 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,083

per person

Nov 17 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Breakfast had some cold cuts, but for a vegan there wasn't much more options than your standard US continental. The TV (which turns on automatically every time you enter the room - very annoying) was the worst setup I've seen in a hotel, the connection to cast wasn't working because the TV wasn't connected to wifi, the remote was weird (no volume/channel controls). Lobby was nauseatingly over-fragranced, makes me wonder what horrible scent they're trying to cover up. Tried to use the stairs instead of the slow elevators and couldn't get out on the 2nd floor for breakfast since the stair exits are locked. Overall fair to ok but missing the attention to detail that would've been nice at the price point. I definitely wouldn't stay for business travel.

Reviewed on Sep 9, 2026

The Talbott, Autograph Collection

Downtown Chicago

CA $1,226

per person

Nov 17 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (165 reviews)

Old,

Reviewed on Sep 8, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $2,165

per person

Nov 17 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

Arlo Chicago

Downtown Chicago

CA $1,158

per person

Nov 17 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,326 reviews)

The room was very clean and neat. The staff was kind.

Reviewed on Sep 9, 2026

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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 $1,847

per person

Nov 19 - Nov 23

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,006 reviews)

Amazing

Reviewed on Sep 8, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $2,165

per person

Nov 17 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

The Peninsula Chicago

Downtown Chicago

CA $2,604

per person

Nov 19 - Nov 23

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,001 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 $875

per person

Oct 26 - Oct 29

found 20 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Reviewed on Sep 9, 2026

The Talbott, Autograph Collection

Downtown Chicago

CA $922

per person

Oct 26 - Oct 29

found 20 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (165 reviews)

Old,

Reviewed on Sep 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,672

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,681 reviews)

The view is stunning! Just a heads up for those without a car: it’s quite a walk even to the bus terminal, which can be pretty exhausting after a long day of exploring.

Reviewed on Sep 9, 2026

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4 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 $1,205

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Reviewed on Sep 9, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,745

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

Swissotel - Chicago

Downtown Chicago

CA $1,580

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,512 reviews)

Good proximity to the river and local sights. Property is a little dated and the driveway is always full of cars. Rooms could use a refresh. Shower is very small.

Reviewed on Sep 9, 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 $801, 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 36.

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! (1,044 reviews)

"Good location. Lots of restaurants and stores to shop. Very close to Loyola. Close to bus and trains making it easy to get around. Hotel rooms were clean and well maintained. Hotel staff was very helpful. Breakfast included with room was the typical for the brand. We had a great stay."

Reviewed on Sep 7, 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. ...

Great Location-Beautiful Friendly Andersonville Neighborhood

Chicago IL

4 min drive from Loyola University Chicago

Stay at this apartment in Chicago. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wrigley Field and Lincoln Park Zoo are located ...

10/10 Exceptional! (215 reviews)

"Nice property. Clear instructions"

Reviewed on Aug 23, 2026

See all 5,048 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.