Highland Park Vacations from $522

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $522 per person
$522
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Loved this hotel and their customer service. Overall, a great experience, highly recommend.

Reviewed on Jul 4, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,141, price is now $744 per person
$744
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on Jul 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,040, price is now $686 per person
$686
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Excellent customer service, amazing staff!

Reviewed on Jul 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,343, price is now $925 per person
$925
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Me encantó volveria mil veces a ese hotel

Reviewed on Jul 4, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,422, price is now $980 per person
$980
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
We generally stay here when we travel to Chicago by the quality of service has diminished lately. Additionally if your booking is through Expedia, everything gets complicated and not well treated.

Reviewed on Jul 5, 2026

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Stay near popular Highland Park attractions

Ravinia Park

8.4/10 (5 reviews)
Ravinia Park hosts North America's oldest outdoor music festival in a picturesque setting. Enjoy performances while picnicking on the lawn, with the Chicago Symphony Orchestra often featured during summer evenings.
See properties

What to do in Highland Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$22
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

$31
per adult
96% of travellers recommend
Flyover in Chicago
See all activities in Highland Park

Highland Park Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$172 nightly
The price is $204 total per night from Jul 6 to Jul 7
$204 total
Jul 6 - Jul 7
Total with taxes and fees
8.2/10 Very Good! (1,689 reviews)
"We like our room, very clean and spacious"

Reviewed on Jul 4, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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
$259 nightly
The price is $304 total per night from Jul 6 to Jul 7
$304 total
Jul 6 - Jul 7
Total with taxes and fees
8.4/10 Very Good! (2,319 reviews)
"Very convenient location for a short stay"

Reviewed on Jul 4, 2026

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
$169 nightly
The price is $193 total per night from Jul 6 to Jul 7
$193 total
Jul 6 - Jul 7
Total with taxes and fees
8.8/10 Excellent! (2,773 reviews)
"The staff were so kind and friendly."

Reviewed on Jul 4, 2026

Hyatt Regency O'Hare Chicago
See all 2,584 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.

Find the Best Highland Park Vacation Packages

Highland Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
29,700
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Marriott Theatre, North Shore Center for the Performing Arts and Kohl Childrens Museum

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Frequently asked questions

How much does a Highland Park vacation package cost?
You'll find cheap prices from $522 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.