Highland Park Trip

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Top Highland Park Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,755 reviews)
beautiful hotel, friendly and helpful staff.

Reviewed on 2 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
This was our second stay here. We were particularly impressed by the staff and customer service. It’s the kind we get in 5stars hotels overseas in the Middle East or SouthEast Asia. Impeccable. A special shout out to Pablo Criado for his warm and enthusiastic welcome and making sure that we had a great stay! I am now a fan and will only stay at Trump Chicago when in Chicago downtown.

Reviewed on 5 Jul 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,796 reviews)
Room was tiny for the price and no coffee maker in the room!

Reviewed on 5 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out

Reviewed on 29 Jun 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,822 reviews)
Love this hotel Location,food and staff they are amazing

Reviewed on 5 Jul 2025

Top hotels in Highland Park

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 ₹16,327 per night from 26 Jul to 27 Jul
₹16,327
₹19,167 total
26 Jul - 27 Jul
includes taxes & fees
8/10 Very Good! (2,049 reviews)
"Convenient to airport after flight got cancelled not once but twice ."

Reviewed on 2 Jul 2025

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
The price is ₹726 per night from 7 Jul to 8 Jul
₹726
₹14,881 total
7 Jul - 8 Jul
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Great location and decent rooms. I had a strange experience in that two days in to my four day stay management ( dressed in plain, casual clothes of shorts and tshirt) came to my door and told me I wasn’t supposed to be in my room; that my room was supposed to be vacant. I would have questioned wether ..."

Reviewed on 2 Jul 2025

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
The price is ₹13,748 per night from 5 Aug to 6 Aug
₹13,748
₹15,671 total
5 Aug - 6 Aug
includes taxes & fees
8.6/10 Excellent! (1,701 reviews)
"I like it because I get to relax"

Reviewed on 4 Jul 2025

Hyatt Regency O'Hare Chicago
See all 2,498 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Navy Pier

Navy Pier

4/5(125 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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

Frequently asked questions

How much does a Highland Park holiday package cost?
You'll find cheap prices from ₹43,356 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 holiday to Highland Park costs.
What are the cheapest months to go to Highland Park?
If you'd like to score a cheap Highland Park holiday package, consider visiting in December, January and February. You're likely to find lower rates on hotels and flights during these months --- perfect for a budget-friendly getaway.
How many days is enough for Highland Park?
We'd suggest booking a Highland Park holiday for a minimum of 2 days. This will give you plenty of time to visit top sights including Ravinia Park and Highland Park Country Club, as well as explore neighbourhoods like Riverwoods and Bannockburn. You might even be able to make time for a day trip or two from Highland Park.
Is it worth booking a holiday package to Highland Park?
Whether you're looking to check out major sights like Chicago Botanic Garden and Ravinia Pavilion on your Highland Park holiday, or coming for its great shopping, golfing and dining, there's something for everyone here. With so much to experience, you'll soon find out why so many families think Highland Park is a good holiday destination.
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 holiday as a package?
You can enjoy significant savings on your Highland Park escape by booking a personalised holiday 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 holiday 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. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Highland Park.
  2. Budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Highland Park.
  3. Decide how long to go for: Now that you know more about Highland Park, you can work out the right length of your holiday. Put together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customised Highland Park holiday package.

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