Name: NEW! BEACHFRONT LAKE VIEW Lake Michigan Condo-private beach/heated pool/sundeck!
Rating: 9.2

Top Holiday Package Deals in North Side

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $957

per person

Jun 18 - Jun 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very Good! (2,683 reviews)

Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.

Reviewed on May 7, 2026

Swissotel - Chicago

Downtown Chicago

CA $962

per person

Jun 18 - Jun 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,293 reviews)

Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on May 6, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,142

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,478 reviews)

My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again

Reviewed on May 6, 2026

Level Chicago - River North

Downtown Chicago

CA $1,036

per person

Jun 25 - Jun 28

found 15 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (973 reviews)

Everything was clean and great

Reviewed on May 6, 2026

Fairmont Chicago at Millennium Park

Downtown Chicago

CA $1,148

per person

Jun 30 - Jul 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (2,144 reviews)

Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on May 5, 2026

Where to stay in North Side

Find the best North Side areas and neighborhoods for the activities you enjoy most. Learn more about North Side

Downtown

2 out of top 10 points of interest in this area

If you're spending some time in Downtown, South Haven Center for the Arts and Warner Vineyards are top sights worth seeing.

North Side Hotel Deals

1-bedroom cottage steps to Lake Michigan Beach fire pit

South Haven MI

10/10 Exceptional! (187 reviews)

Is a wonderful place. Everything and more than I expected. Great location. Great host.I plan on returning.

Reviewed on May 1, 2026

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NEW! BEACHFRONT LAKE VIEW Lake Michigan Condo-private beach/heated pool/sundeck!

South Haven MI

9.2/10 Wonderful! (15 reviews)

It was beautiful

Reviewed on Oct 26, 2025

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Yelton Manor Bed & Breakfast

140 North Shore Drive South Haven MI

Fully refundableReserve now, pay when you stay

CA $253

CA $281 total

May 31 - Jun 1

includes taxes & fees

9.2/10 Wonderful! (123 reviews)

Loved the cozy feeling and ambiance of the B&B. Location was great , as we could walk to the beach. Breakfast was delicious with fresh fruit every morning.

Reviewed on May 3, 2026

See all 2,131 properties in 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.