Highland Park Vacations

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Find the Best Highland Park Vacation Packages

Highland Park Hotel Deals

Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundable
The price is SAR 447 per night from Apr 16 to Apr 17
SAR 447
SAR 509 total
includes taxes & fees
16 Apr - 17 Apr
8.6/10 Excellent! (1,456 reviews)
"Beautiful hotel with many amazing amenities. My only negative was the front desk not knowing simple requests like “where to get a coffee to go in the morning”."

Reviewed on 7 April 2025

Hyatt Regency O'Hare Chicago
Hyatt Regency Schaumburg Chicago
Hyatt Regency Schaumburg Chicago
4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is SAR 402 per night from Apr 17 to Apr 18
SAR 402
SAR 462 total
includes taxes & fees
17 Apr - 18 Apr
8.4/10 Very Good! (1,018 reviews)
"It was really good we enjoyed our stay and hotel was quite and clean. But the only issue was when i chose the room it said on the site that it sleeps 6 people because i was expecting sofa bed that was included."

Reviewed on 6 April 2025

Hyatt Regency Schaumburg Chicago
Ambassador Hotel Chicago
Ambassador Hotel Chicago
4 out of 5
1301 N State Pkwy, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is SAR 157 per night from Apr 14 to Apr 15
SAR 157
SAR 614 total
includes taxes & fees
14 Apr - 15 Apr
8.6/10 Excellent! (986 reviews)
"The best features of the hotel is the staff. From all receptionists, servers, valet and the cleaning lady, everybody was very friendly, helpful and accommodating. The hotel has an "old soul" feel and could use sprucing up just a little. Not too many options for dinner in the area. I do highly recommend ..."

Reviewed on 4 April 2025

Ambassador Hotel Chicago
See all 2,319 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?
You’ll find cheap prices on Expedia for your Highland Park escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Highland Park costs.
What are the cheapest months to go to Highland Park?
If you’d like to score a cheap Highland Park vacation package, consider visiting in December, January and February. You’re likely to find lower rates on hotels and flights during these months — perfect for a budget-friendly getaway.
How to find the best Highland Park package deals?
Start your search for a Highland Park package deal by entering your destination and travel dates under our “Packages” tab. Then add some filters, like “Property type” and “Amenities,” to fine-tune the results to your exact style. You can also sort by “Package discount” and browse offers that come with unbeatable savings. If you don’t find the ideal Highland Park package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Highland Park adventure underway.
Is it cheaper to book a Highland Park vacation as a package?
You can enjoy significant savings on your Highland Park escape by booking a personalized vacation package. Check the “Package” heading, then enter your travel dates and destination to see the best hotel prices and airfares. 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 vacation package to Highland Park?
Enjoy incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Highland Park break.
How to plan a trip to Highland Park?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Highland Park.
  2. Budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Highland Park.
  3. Decide how long to go for: Now that you know more about Highland Park, you can work out the right length of your vacation. Put together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Highland Park vacation package.

Discover the most popular places to visit in Highland Park

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(1,805 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place