North Shore Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,270, price is now CA $872 per person
CA $872
per person
Sep 25 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,858 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,699, price is now CA $1,088 per person
CA $1,088
per person
Sep 25 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Very pleasant stay and cleanliness

Reviewed on Jul 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,396, price is now CA $925 per person
CA $925
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (504 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,700, price is now CA $1,202 per person
CA $1,202
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Price was CA $1,421, price is now CA $1,035 per person
CA $1,035
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
An amazing stay 100% recommended

Reviewed on Jul 29, 2026

Ready to book your vacation to North Shore?

 

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North Shore Hotel Deals

DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83 Mundelein IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Aug 29 to Aug 30
CA $162
CA $180 total
Aug 29 - Aug 30
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Hotel was really clean and eco friendly, and friendly staffs."

Reviewed on Jul 29, 2026

DoubleTree by Hilton Libertyville - Mundelein
Red Roof Inn PLUS+ Chicago - Hoffman Estates

Red Roof Inn PLUS+ Chicago - Hoffman Estates

2.5 out of 5
2500 Hassell Road Hoffman Estates IL
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Aug 12 to Aug 13
CA $94
CA $106 total
Aug 12 - Aug 13
includes taxes & fees
Red Roof Inn PLUS+ Chicago - Hoffman Estates
Best Western Plus Elgin - Chicago

Best Western Plus Elgin - Chicago

3 out of 5
2175 Marriott Dr West Dundee IL
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Aug 5 to Aug 6
CA $124
CA $139 total
Aug 5 - Aug 6
includes taxes & fees
Best Western Plus Elgin - Chicago
See all 350 properties in North Shore
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a North Shore vacation package cost?
Offering excellent value package deals from CA $872 on Expedia, you'll be thrilled with how little a vacation to North Shore costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to North Shore?
If you're looking to book a cheap North Shore vacation package, consider visiting in January, February and March. You're likely to find lower prices on airfares and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for North Shore?
With a well-planned schedule, you can easily visit the most popular North Shore attractions in a handful of days. But if you want to discover hidden gems or go on day tours, think about booking your North Shore vacation for longer.
How to find the best North Shore package deals?
Finding a cheap North Shore package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly North Shore package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a North Shore vacation as a package?
You can enjoy significant savings on your North Shore break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to North Shore?
Enjoy amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment North Shore getaway.
How to plan a trip to North Shore?

  1. Choose your dates: What you want to do in North Shore and your favourite season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to flights and activities. Your accommodations will likely be the biggest expense during your trip to North Shore.
  3. Decide your trip length: Think about how long you want to spend discovering North Shore. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the ideal North Shore vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.