Highland Park Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Highland Park

Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$237 per night from 24 Dec to 25 Dec
S$237
includes taxes & fees
24 Dec - 25 Dec
9/10 Wonderful! (1,009 reviews)
"Great hotel. Great location with a super friendly staff"

Reviewed on 21 Nov,2024

Thompson Chicago, by Hyatt
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$326 per night from 24 Nov to 25 Nov
S$326
includes taxes & fees
24 Nov - 25 Nov
7.8/10 Good! (2,061 reviews)
"Everything is great"

Reviewed on 21 Nov,2024

Hilton Chicago O'Hare Airport
Chicago Getaway Hostel
Chicago Getaway Hostel
2 out of 5
616 W Arlington Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 24 Nov to 25 Nov
S$97
includes taxes & fees
24 Nov - 25 Nov
8.8/10 Excellent! (1,004 reviews)
"Would highly recommend"

Reviewed on 21 Nov,2024

Chicago Getaway Hostel
See all 2,243 properties in Highland Park
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.

Frequently asked questions

How much does a Highland Park holiday package cost?
From just , you can custom build your Highland Park holiday package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Highland Park?
Secure flights that fit your schedule, add a hotel room to your booking and watch the savings grow with a Highland Park holiday package. It’s that easy! From flights and hotels to rental cars and activities, Expedia is where your cheap holiday begins. And with over 550 airlines and 1,000,000 properties across the globe to select from, you’ll never be short of choice.
Where should I stay in Highland Park?
You’ll want to stay where the action is. Many visitors like to book hotels around popular sights, like Chicago Botanic Garden, Ravinia Pavilion and Ravinia Park.
What are the top hotels in Highland Park?
Whether you’re planning to stay for just one night or a week in Highland Park, you’ll get a great night’s sleep at Courtyard by Marriott Chicago Highland Park/Northbrook. This option is popular with many travellers.
How far in advance should I book my Highland Park holiday?
Smart travellers will likely want to reserve their seats as early as possible. You can generally start comparing international airfares on Expedia up to 12 months before your flight. If you’ve left booking to the last minute, fear not. Discounted prices sometimes occur just weeks before departure dates.
What does an Expedia Highland Park travel package include?
Select from any combination of rental cars, flights and hotels. Once you’ve made your booking, you can add activities and experiences. Want to pick your fare class? That’s also easy to do. The choice is yours when it comes to organising your ideal Highland Park getaway.
What should I know before booking a Highland Park travel package?
You’ll score excellent savings when you bundle your flights, hotels and rental cars into a package. Plus, booking everything together just makes things easier. So why waste your time or money? Whether you’re putting together an upscale romantic escape or a low-cost family break, browse our package deals today.
Can I choose my airline with a Highland Park Expedia holiday package?
Expedia has access to more than 550 airline partners worldwide, so you certainly can. Simply choose the airline you want and create the perfect Highland Park escape.
If I'm not able to travel, can I cancel my Highland Park holiday package?
If your travel plans in Highland Park have been upended, it’s good to know that you can amend or cancel your booking. If your booking was made in the last 24 hours, you may be able to get a refund. If your booking is older than that, your hotel, airline or car rental company may impose fees. For more details, check our Customer Service Portal.

Popular places to visit

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
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
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 Highland Park

Flyover in Chicago

Flyover in Chicago

S$50
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

S$58
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

S$71
Per adult
94% of travellers recommend
Architecture River Tour
See all activities in Highland Park

* 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.