Highland Park Vacations from $540

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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $824, price is now $540 per person
$540
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
we didn't have breakfast at the hotel

Reviewed on May 11, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,780, price is now $1,093 per person
$1,093
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too

Reviewed on May 3, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,146, price is now $721 per person
$721
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,086, price is now $692 per person
$692
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,991 reviews)
Great location & breakfast was amazing.

Reviewed on May 11, 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 $1,092, price is now $709 per person
$709
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

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Discover the most popular places to visit in Highland Park

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

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

Navy Pier

What to do in Highland Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

$40
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Highland Park

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
$247 nightly
The price is $290 total per night from Jun 7 to Jun 8
$290 total
Jun 7 - Jun 8
Total with taxes and fees
8.4/10 Very Good! (2,293 reviews)
Wonderful

Reviewed on May 12, 2026

Hilton Chicago O'Hare Airport
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
$149 nightly
The price is $178 total per night from May 27 to May 28
$178 total
May 27 - May 28
Total with taxes and fees
8.2/10 Very Good! (1,436 reviews)
Rooms are only cleaned every three days but they don’t tell you that at check in. No towels or toilet paper restocked. Rooms are just okay. Free drink tickets at bar that doesn’t open until 5 pm. Gee thanks. Breakfast is Waffle House level. It’s okay but not great. Lobby is beautiful.

Reviewed on May 12, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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
$169 nightly
The price is $193 total per night from May 21 to May 22
$193 total
May 21 - May 22
Total with taxes and fees
8.8/10 Excellent! (2,553 reviews)
I was awakened early by drilling right under my bed. I understand construction, but the noice in a hotel especially jack hammering shouldn’t start until after 10AM as some guests don’t get in until late and being that it is an airport hotel jet lagged.

Reviewed on May 12, 2026

Hyatt Regency O'Hare Chicago
See all 2,674 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 $540 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.

Explore a world of travel with Expedia

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