Itasca Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Itasca Flight & Hotel Packages

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
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
No refrgerator, can hear the noise coming from the street. Room us clean and smell good

Reviewed on 14 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
It’s not what I was expecting, I was expecting something different , no views, not happy at all

Reviewed on 14 Jul, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Great location, but the $50.00 early check-in fee is ridiculous. Also, the comforter on the bed has seen better days.

Reviewed on 15 Jul, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on 15 Jul, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
I didn't like property didn't have free parking.

Reviewed on 15 Jul, 2025

Top hotels in Itasca

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 S$169 per night from 3 Aug to 4 Aug
S$169
3 Aug - 4 Aug
includes taxes & fees
8.6/10 Excellent! (1,015 reviews)
"I arrived with a family of 5 for a weekend stay . While my mom and son were checking in their front desk person was very informative about the property (restaurant hours,gym hours ,do you need more than one key,what the property has to offer ,what’s close by ) etc however my front desk representative ..."

Reviewed on 14 Jul, 2025

The Westin Chicago Northwest
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 S$233 per night from 20 Jul to 21 Jul
S$233
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
"Excellent place and service"

Reviewed on 12 Jul, 2025

Eaglewood Resort and Spa
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is S$221 per night from 10 Aug to 11 Aug
S$221
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,247 reviews)
"Easy check in, room was pretty spacious and in a great location. Very friendly staff"

Reviewed on 12 Jul, 2025

Crowne Plaza Chicago West Loop by IHG
See all 3,398 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Itasca

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Itasca

Frequently asked questions

How much does an Itasca holiday package cost?
You'll find cheap prices from S$437 on Expedia for your Itasca break. However, factors like the length of stay, hotel choice and season will determine how much your holiday to Itasca costs.
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 holiday packages and you could land some great off-season discounts.
How many days is enough for Itasca?
With a well-organised travel plan, you can easily visit the most popular Itasca sights in a few days. But if you'd like to explore off the beaten track or go on day trips, think about booking your Itasca holiday for longer.
How to find the best Itasca package deals?
Start your search for an Itasca package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Itasca package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Itasca adventure underway.
Is it cheaper to book an Itasca holiday as a package?
You can enjoy significant savings on your next Itasca break by booking a personalised holiday package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Itasca?
If you're planning a spur-of-the-moment Itasca getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Itasca?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Itasca.
  2. Budget wisely: As well as the price of your stay, you'll need to consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Itasca.
  3. Decide how long to go for: Now that you're more familiar with Itasca, you can work out the right length of your break. Pull together a rough plan and allocate enough time to cover everything you want to see.
  4. Bundle your accommodation and airfare: After you've settled on your trip dates and duration, lock in the right Itasca holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.