Itasca Vacation Packages

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  • Better together

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

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

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Your Itasca Vacation

Come and experience this wonderful city for yourself with a Itasca vacation package. Consider spending a few days in the neighborhood of Jefferson Park, which is great for festivals and culture, and your time here will be nothing short of unforgettable. A trip to Itasca is an ideal opportunity to take in the sights. Be sure to stop by well-known attractions like Woodfield Mall, LEGOLAND® Discovery Center and TopGolf Chicago. Stop dreaming and start traveling. Browse the range of options on Expedia today and put your Itasca vacation plans into action!

Top Itasca Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,305, price is now CA $975 per person
CA $975
per person
Jan 21 - Jan 24
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Staff was very inviting and courteous. Room was clean. Valet was very very kind and prompt. I cannot say enough great things about the valet associates. They were very friendly.

Reviewed on Nov 9, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,394, price is now CA $992 per person
CA $992
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,801, price is now CA $1,315 per person
CA $1,315
per person
Jan 21 - Jan 24
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,343, price is now CA $988 per person
CA $988
per person
Dec 31 - Jan 4
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Ready to book your vacation to Itasca?

 

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Itasca Hotel Deals

Hyatt Place Itasca

Hyatt Place Itasca

3 out of 5
1150 North Arlington Heights Road Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Nov 13 to Nov 14
CA $151
CA $168 total
Nov 13 - Nov 14
includes taxes & fees
Hyatt Place Itasca
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Dec 9 to Dec 10
CA $168
CA $218 total
Dec 9 - Dec 10
includes taxes & fees
8.8/10 Excellent! (1,414 reviews)
"A little luster off it's orifin"

Reviewed on Nov 9, 2026

Eaglewood Resort and Spa
The Westin Chicago Northwest

The Westin Chicago Northwest

4 out of 5
400 Park Blvd Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Nov 22 to Nov 23
CA $167
CA $187 total
Nov 22 - Nov 23
includes taxes & fees
The Westin Chicago Northwest
See all 3,531 properties in Itasca
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

What to do in Itasca

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Itasca

Frequently asked questions

How much does an Itasca vacation package cost?
Offering great value package deals from CA $975 on Expedia, you'll be pleasantly surprised at how much a vacation to Itasca costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Itasca?
You can typically find lower prices and greater availability in January, February and November. Explore our cheap Itasca vacation packages and you could land some great off-season deals.
How many days is enough for Itasca?
We'd suggest booking an Itasca vacation for at least 2 days. This gives you time to visit top sights including Pirates Cove Childrens Theme Park and The Oasis Water Park, as well as explore neighbourhoods like Medinah and South Addison. You might even be able to fit in one or two day trips beyond Itasca.
How to find the best Itasca package deals?
Landing a cheap Itasca package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Itasca package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book an Itasca vacation as a package?
You can enjoy significant savings on your Itasca retreat by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Itasca?
Land fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Itasca getaway.
How to plan a trip to Itasca?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Itasca.
  2. Plan your budget wisely: On top of the price of your accommodations, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that may come up during your trip to Itasca.
  3. Work out your trip length: Consider how much time you want to spend exploring Itasca. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: After you've nailed down your dates and duration, book the right Itasca 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.