Highland Park Vacations from $355

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Your Highland Park Vacation

Planning your next big adventure is a piece of cake with a Highland Park vacation package. The neighborhood of Riverwoods, which is great for nature, makes a superb base to uncover the marvels of this unique city. If sightseeing is part of the plan during your trip to Highland Park, check out well-known attractions like Chicago Botanic Garden, Lake Forest College and Northbrook Sports Complex. Whoever you're escaping with and whatever you plan to spend, your dream Highland Park vacation is just clicks away with Expedia.

The Latest Highland Park vacation packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago - Glenview by IHG

Staybridge Suites Chicago - Glenview by IHG

3 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The room was very clean! I loved having an ice maker too! The staff was very helpful too. Highly recommend this hotel!

Reviewed on Aug 8, 2025

Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,009 reviews)
Some of the he seating areas, were not suitable, too low for comfort at the tables.

Reviewed on Aug 11, 2025

Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
It was what you’d expect for that price and type of hotel

Reviewed on Aug 1, 2025

Fairfield Inn & Suites by Marriott Chicago Naperville

Fairfield Inn & Suites by Marriott Chicago Naperville

2.5 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (1,007 reviews)
The room is very damped, smell wet. The carpet, wall, bathroom, overall looks really outdated. Probably not going to stay here again anytime soon. Great breakfast though.

Reviewed on Aug 10, 2025

Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
6.8/10 (1,001 reviews)
Everyone was very nice and we could check in late which I liked

Reviewed on Aug 7, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Highland Park

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

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

Michigan Avenue

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

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

Navy Pier

What to do in Highland Park

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Highland Park

Highland Park Hotel Deals

Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $160 total per night from Aug 24 to Aug 25
$160 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (1,287 reviews)
Beautiful first trip to Chicago
"Loved the neighborhood. The room was beautiful. Liked popcorn snack at wine hour. Walking distance to the beach and Starbucks. Excellent brunch place couple steps away. Nice common area to relax. They let me check in an hour early. Nice safe neighborhood"

Reviewed on Aug 9, 2025

Claridge House
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
$179 nightly
The price is $210 total per night from Sep 5 to Sep 6
$210 total
Sep 5 - Sep 6
Total includes taxes and fees
8/10 Very Good! (2,086 reviews)
"The room was comfortable and very quiet despite the proximity to the airport. I would have preferred a queen size bed, but the only available option was a double."

Reviewed on Aug 9, 2025

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Aug 24 to Aug 25
$154 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,825 reviews)
"Good location. Nice lobby. Overall a very dated hotel."

Reviewed on Aug 9, 2025

Hyatt Regency O'Hare Chicago
See all 2,574 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.

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Frequently asked questions

How much does a Highland Park vacation package cost?
You'll find cheap prices from $355 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're hoping to book a cheap Highland Park vacation package, consider visiting in February, March and December. You'll generally find better rates on flights and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Highland Park?
You can easily explore all the major attractions in Highland Park within a few days, including the popular Highland Park Country Club. If you're after an extended Highland Park vacation, check out what sort of day trips and activities are available nearby.
Is it worth booking a vacation package to Highland Park?
Well known for its shopping, golfing and dining, a Highland Park vacation is a hit with all types of travelers. Be sure to check out top sights like Chicago Botanic Garden and Ravinia Pavilion, and consider renting a car for day trips to explore even more.
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. Pick the right time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Highland Park.
  2. Set a budget: Consider costs such as flights, food and transportation when working out how much to set aside for your trip to Highland Park. Then, select a hotel that works with your budget, whether that's an affordable option or a deluxe retreat.
  3. Organize your Highland Park escape with Expedia's trip planning tool: Search for and book stays and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Highland Park together.
  4. Decide how long to go away for: Now that you know more about Highland Park, you can work out the right length of your break. Put together a rough plan and give yourself enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Highland Park vacation package.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Highland Park's highlights. Find all the fun things to do in Highland Park with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Highland Park vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Highland Park vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.