Highland Park Vacations

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Find the Best Highland Park Vacation Packages

Highland Park Hotel Deals

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 AED 750 per night from Mar 1 to Mar 2
AED 750
AED 880 total
1 Mar - 2 Mar
includes taxes & fees
8.2/10 Very Good! (2,218 reviews)
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on 9 February 2026

Hilton Chicago O'Hare Airport
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 AED 526 per night from Feb 27 to Feb 28
AED 526
AED 617 total
27 Feb - 28 Feb
includes taxes & fees
8.6/10 Excellent! (1,219 reviews)
aa

Reviewed on 5 February 2026

Marriott Chicago O'Hare
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd Rosemont IL
Fully refundable
The price is AED 433 per night from Feb 16 to Feb 17
AED 433
AED 494 total
16 Feb - 17 Feb
includes taxes & fees
8.6/10 Excellent! (2,728 reviews)
Everything was great

Reviewed on 30 January 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 2,723 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.

Discover the most popular places to visit in Highland Park

Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Navy Pier
Chicago Riverwalk which includes a city, a bay or harbor and a river or creek

Chicago Riverwalk

4.5/5(1,535 reviews)

After visiting Chicago Riverwalk, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront in this vibrant area, or check out its top-notch restaurants.

Chicago Riverwalk

Frequently asked questions

How do I find cheap flights to Highland Park that have flexible change policies?
By using our convenient "No change fee" filter, that's how. All you have to do is enter your travel details, click the "Search" button, then tick the box directly under the "Flexible change policies" subheading (left-hand side of your screen). Expedia makes it a snap to find flexible, low-cost tickets to Highland Park.
Which airlines fly to Highland Park?
When it's time for a well-deserved break, these well-known airlines will make escaping to Highland Park super easy:

  • United Airlines - 13,009 flights to or near Highland Park each month, including 13,005 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 10,036 flights to or near Highland Park each month, including 10,036 flights to O'Hare Intl. Airport (ORD) per month.

How can I find cheap tickets to Highland Park?
An effective strategy for nabbing cheap airfares is to be flexible with your dates. Begin with searching for your flight to Highland Park, then click on the "flexible dates" link to see prices for nearby days. Another helpful hint? Book well ahead of time. For an idea of fares, was the lowest price for a flight to Highland Park in the last seven days.
How much is a flight to Highland Park?
You could have scored a round-trip flight to Highland Park from anywhere between and in the last seven days. For one-way journeys leaving from (), the lowest amount paid during this period was just .
What are the most popular airports to fly into in Highland Park?
When it comes to planning which airport in Highland Park to jet into, here are your options:

  • O'Hare Intl. Airport (ORD) - 26,484 flights per month.
  • Midway Intl. Airport (MDW) - 6,439 flights per month.

When is the cheapest time to fly to Highland Park?
Jet off on a Tuesday to boost your chances of bagging the cheapest airfare to Highland Park. Mondays are usually the second most affordable day to take off. Saturday is typically the priciest day to fly anywhere.
How much is a plane ticket to Highland Park?
In the last seven days, airfares cost between and . Have a look at our unbeatable deals to Highland Park, make a booking and then get ready for your getaway!
What months are the cheapest to book a flight to Highland Park?
February is the most affordable month to reserve a seat for your Highland Park vacation. Airfares are priciest over the month of December, so avoid this time if possible.
How long is a flight to Highland Park?
Your flight to Highland Park could be short or long depending on where you travel from. Before you fill your laptop with movies and TV shows, check out the average flight times for these top domestic routes:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 37 minutes
  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 34 minutes
  • Phoenix, AZ (PHX-Sky Harbor Intl.) to O'Hare Intl. Airport (ORD) - 3 hours and 17 minutes