Highland Park Vacations from $389
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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.
Travelodge by Wyndham Downtown Chicago
Downtown Chicago
$389
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (2,711 reviews)
Affordable option less than a block off Michigan avenue. While it is an older property, the room was very clean, and the staff did an excellent job refreshing the room each morning. Our room was on the inside of the building and we heard NO city noise during the night. Easy access to the train and buses. Very good Thai restaurant right next door, as well as a small diner for breakfast. I would definitely stay here again!
Reviewed on Aug 11, 2026
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$596
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,933 reviews)
The Hotel is located in a great area. Unfortunately it’s an older hotel and you can hear others through the wall with the rooms next to yours. If your room is facing the street there is street noise. The room was clean a little dated as it’s an older hotel. The staff were super friendly and helpful. I would probably only stay here again if the other hotels in the area I normally stay at are not available which is why I ended up at the hotel.The bakery coffee place in the lobby was good. I didn’t utilize the restaurant.
Reviewed on Aug 11, 2026
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View all tripsStay 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.
Ravinia Pavilion
9.6/10 (7 reviews)
Ravinia Pavilion hosts classical, jazz, and pop performances in a park-like setting. Enjoy concerts from covered seats or bring a gourmet picnic for the expansive lawn experience.
What to do in Highland Park
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Highland Park Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$125 nightly
$148 total
Aug 30 - Aug 31
Total with taxes and fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$230 nightly
$270 total
Sep 11 - Sep 12
Total with taxes and fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$169 nightly
$193 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (3,004 reviews)
"The Hyatt is a perfect place to enjoy Chicago is you want to stay close to the airport. Public transportation is close and easily accessible, the hotel is immaculately cleaned, and the staff helped in every way possible. I definitely recommend this hotel"
Reviewed on Aug 11, 2026
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 $389 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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
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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.
