Highland Park Holidays

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Top Highland Park Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
per person
6 Aug - 8 Aug
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8/10 Very Good! (2,380 reviews)
The main lobby was inviting. Breakfast was provided. The food on the breakfast bar was only mildly warm but the omelettes were good. The staff were friendly and helpful.

Reviewed on 18 Jun 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Aug - 8 Aug
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,230 reviews)
Location is amazing, super friendly staff. Will definitely be back soon

Reviewed on 17 Jun 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
6 Aug - 8 Aug
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (1,166 reviews)
We like staying at this property because it is convenient to many shopping and restaurant venues within a couple blocks. The only thing that we didn’t like is that sometimes the unhoused individuals would come into the Ground floor entrance and beg for money. The security desk is not manned at times. Other than that, the property is well kept and the staff is incredible! This was our second time staying here and we will stay again.

Reviewed on 17 Jun 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
6 Aug - 8 Aug
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (1,114 reviews)
Amazing property in terms of location and amenities

Reviewed on 17 Jun 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
6 Aug - 8 Aug
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.6/10 Exceptional! (983 reviews)
I would just improve the attention in the breakfast restaurant due to a bad experience. The rest was excellent

Reviewed on 2 Jun 2024

Top hotels in Highland Park

Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
Fully refundable
The price is HK$1,215 per night from 30 Jun to 1 Jul
HK$1,215
per night
30 Jun - 1 Jul
9/10 Wonderful! (1,008 reviews)
"The room had a dinky little espresso machine but no coffee. Ordering coffee to the room was insanely expensive. $5 just for ordering cream with the coffee. Really disappointing how they gouge you for coffee. Everything else was fantastic."

Reviewed on 16 Jun 2024

Thompson Chicago, by Hyatt
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 HK$1,242 per night from 1 Jul to 2 Jul
HK$1,242
per night
1 Jul - 2 Jul
8/10 Very Good! (1,007 reviews)
"The Staff was Absolutely Amazing Christina & Fernando as well as the entire front desk staff. Though the property is dated an in severe need of update, all and all a great stay! I intend to put visiting guests there!"

Reviewed on 15 Jun 2024

Marriott Chicago O'Hare
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is HK$1,398 per night from 6 Jul to 7 Jul
HK$1,398
per night
6 Jul - 7 Jul
9.2/10 Wonderful! (1,604 reviews)
"I didn't like view, Dining options were perfect"

Reviewed on 16 Jun 2024

Loews Chicago O'Hare Hotel
See all 2,337 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 vacation package cost?
From just HK$3,191, you can custom build your Highland Park vacation 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 vacation package. It’s that easy! From flights and hotels to rental cars and activities, Expedia is where your cheap vacation 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 Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Highland Park

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

HK$1,031
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Museum of Contemporary Art: General Admission Ticket

Chicago Museum of Contemporary Art: General Admission Ticket

HK$172
Per adult
90% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

HK$367
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture 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.