Highland Park Holidays

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Highland Park Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
18 Jan - 22 Jan
found 18 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
Exceptional management and staff. Great room sizes and the VIP upgraded suite was amazing.

Reviewed on 28 Oct,2024

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
17 Jan - 23 Jan
found 18 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Great property, everything smelled like weed. Front desk staff wasn't warm. Nice property, lighting is DIM even in the bathroom.

Reviewed on 29 Oct,2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
17 Jan - 23 Jan
found 18 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Amazing stay! The staff was super helpful, Danny was Daren were amazing

Reviewed on 27 Oct,2024

InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

4.5 out of 5
Downtown Chicago
per person
17 Jan - 23 Jan
found 18 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (1,769 reviews)
Beautiful hotel with a great pool!!

Reviewed on 31 Oct,2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
18 Jan - 22 Jan
found 18 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Exceeded my expectations. This is my new go-to hotel when in Chicago!

Reviewed on 14 Oct,2024

Top hotels in Highland Park

Marriott Chicago O'Hare
Marriott Chicago O'Hare
3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$262 per night from 8 Nov to 9 Nov
S$262
includes taxes & fees
8 Nov - 9 Nov
8.2/10 Very Good! (1,011 reviews)
"Great"

Reviewed on 28 Oct,2024

Marriott Chicago O'Hare
Crowne Plaza Chicago Ohare Hotel & Conf Ctr, and IHG Hotel
Crowne Plaza Chicago Ohare Hotel & Conf Ctr, and IHG Hotel
3.5 out of 5
5440 N River Rd, Rosemont, IL
Fully refundable
The price is S$190 per night from 1 Dec to 2 Dec
S$190
includes taxes & fees
1 Dec - 2 Dec
8.6/10 Excellent! (1,833 reviews)
"Everything was lovely"

Reviewed on 27 Oct,2024

Crowne Plaza Chicago Ohare Hotel & Conf Ctr, and IHG Hotel
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
3 out of 5
6600 Mannheim Road, building 2, Rosemont, IL
Fully refundable
The price is S$153 per night from 24 Nov to 25 Nov
S$153
includes taxes & fees
24 Nov - 25 Nov
8.6/10 Excellent! (1,475 reviews)
"Good, clean stay... website showed complimentary parking, but was $18 for the night."

Reviewed on 29 Oct,2024

Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
See all 2,202 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 S$7,584, 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

Image for 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
Image for Wrigley Field

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
Image for Millennium Park

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

Image for Flyover in Chicago

Flyover in Chicago

S$50
Per adult
94% of travellers recommend
Flyover in Chicago
Image for Architecture River Tour

Architecture River Tour

S$70
Per adult
94% of travellers recommend
Architecture River Tour
Image for Chicago by Night: 90 Minute River and Lakefront Cruise

Chicago by Night: 90 Minute River and Lakefront Cruise

S$55
Per adult
92% of travellers recommend
Chicago by Night: 90 Minute River and Lakefront Cruise
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.