North Shore Vacation Packages
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Your North Shore Vacation
When a city escape is calling, answer it with a North Shore vacation package. With all your travel plans in order before you go, all you have to do here is concentrate on having a blast. Every trip to North Shore needs a well-designed itinerary. Fill yours with big-name attractions like McHenry County College, Three Oaks Recreation Area and Crystal Lake Park. Browse Expedia's wide range of travel options and start planning your ideal vacation to North Shore today.
Top North Shore Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was CA $1,029, price is now CA $808 per person
CA $808
per person
Aug 28 - Aug 31
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (391 reviews)
We love Wind Creek Hotel/Casino, we have been there several times. This last time the room was clean but smelled bad.
Reviewed on May 30, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,743, price is now CA $1,186 per person
CA $1,186
per person
Aug 27 - Aug 30
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,011 reviews)
I recommend 1000/10, this hotel has everything you need and the location is everything. LOVE LOVE LOVE.
Reviewed on Jun 3, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,668, price is now CA $1,237 per person
CA $1,237
per person
Jul 9 - Jul 12
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,121 reviews)
I absolutely loved it! I little bit noisy but close to literally everything!
Reviewed on Jun 2, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was CA $2,023, price is now CA $1,581 per person
CA $1,581
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,370 reviews)
The hotel was very clean and a great location within Chicago close to restaurants and shopping.
Reviewed on Jun 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,066, price is now CA $1,635 per person
CA $1,635
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
⭐⭐⭐⭐⭐
Amazing stay! Beautiful hotel, incredible views, excellent service, and a perfect location in downtown Chicago. Everything exceeded our expectations. We loved every minute of our stay and would definitely return. Highly recommended!
Reviewed on Jun 4, 2026
North Shore Hotel Deals
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jul 3 to Jul 4
CA $159
CA $176 total
Jul 3 - Jul 4
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Traditional style hotel. Nice large pool area is enclosed. Very well maintained building."
Reviewed on Jun 3, 2026
Sonesta Simply Suites Chicago Libertyville
1100 N Us Route 45 Libertyville IL
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Jun 17 to Jun 18
CA $136
CA $151 total
Jun 17 - Jun 18
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"The dog fee was not shared on Expedia - it was an extra $75."
Reviewed on Jun 4, 2026
Red Roof Inn PLUS+ Chicago - Hoffman Estates
2500 Hassell Road Hoffman Estates IL
Fully refundableReserve now, pay when you stay
The price is CA $86 per night from Jun 23 to Jun 24
CA $86
CA $97 total
Jun 23 - Jun 24
includes taxes & fees
7.8/10 Good! (203 reviews)
"The worst of the worst. Internet never worked. All night with nothing. Staff incompetent!! People outside your door all night walking and talking. I could go on and on but I'll leave it here."
Reviewed on May 31, 2026
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.
Discover the most popular places to visit in North Shore
Crystal Lake Park
After visiting Crystal Lake Park, make a plan to see the other sights and activities in Village of Lakewood. While you're in the area, stroll along the lakeside.
North Wall Rock Climbing
You can take time to visit North Wall Rock Climbing during your travels to Village of Lakewood. While you're in the area, stroll along the lakeside.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
