Highland Vacations from $399

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Your Highland Vacation

Spend less time travel planning and more time having exciting adventures with a Highland vacation package. The neighborhood of East Side, which is good for nature and walking, makes an excellent base for your city break. Like to get out and explore? Hard Rock Casino Northern Indiana, Purdue University Northwest and Hammond Sportsplex & Community Center are three of the leading places to visit during your trip to Highland. Don't delay your visit to this destination any longer. Your ultimate Highland vacation is only a few clicks away with Expedia.

The Latest Highland vacation packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $630, price is now $399 per person
$399
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,120 reviews)
I have stayed at a few Fairmount properties in the past and I would say this was not my favorite of the brand. Overall a nice hotel but not for the price point.

Reviewed on Apr 20, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,194, price is now $740 per person
$740
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (449 reviews)
Everything was amazing from the staff to the amenities, the view and the cleanliness! I will definitely be booking again!

Reviewed on Apr 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $1,028 per person
$1,028
per person
Jun 18 - Jun 22
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
It’s a bit loud on the weekend. There is no daily housekeeping but great space and great location.

Reviewed on Apr 17, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,006, price is now $648 per person
$648
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,266 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on Apr 22, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,249, price is now $823 per person
$823
per person
Jun 16 - Jun 19
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,348 reviews)
Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.

Reviewed on Apr 22, 2026

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Highland Hotel Deals

DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Apr 30 to May 1
$129 total
Apr 30 - May 1
Total with taxes and fees
8.4/10 Very Good! (1,012 reviews)
Clean room, great parking

Reviewed on Apr 23, 2026

DoubleTree by Hilton Chicago - Alsip
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave Oak Lawn IL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $145 total per night from May 3 to May 4
$145 total
May 3 - May 4
Total with taxes and fees
8.4/10 Very Good! (1,297 reviews)
Conveniently located

Reviewed on Apr 22, 2026

Hilton Chicago/Oak Lawn
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
$125 nightly
The price is $147 total per night from May 4 to May 5
$147 total
May 4 - May 5
Total with taxes and fees
6.8/10 (1,003 reviews)
The outside area was okay. The inside was clean, bed was comfortable. There was a microwave (didn’t use) and refrigerator. Large screen tv was nice. Water pressure was just okay. Had some issues checking in because I used my initials (which is what I go by) on my reservation and my ID has my name ...

Reviewed on Apr 21, 2026

Chicago Lake Shore Hotel
See all 925 properties in Highland
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 Vacation Packages

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Midway Intl. Airport (MDW)
Population
22,900
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Whihala Beach, Lake Street Beach and Theatre at the Center

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Frequently asked questions

How much does a Highland vacation package cost?
Offering great value package deals from $399 on Expedia, you'll be surprised at how little a vacation to Highland costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Highland?
If you'd like to book a cheap Highland vacation package, consider traveling in November, December and January. You'll usually find lower prices on accommodations and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Highland?
With a well-organized travel plan, you can easily hit the most popular Highland attractions in a handful of days. But if you'd like to discover hidden spots or go on day trips, consider booking your Highland vacation for longer.
How to find the best Highland package deals?
Use Expedia's handy filters to help you find some unbeatable Highland package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Highland package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Highland vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels individually. Better still, you can tailor your Highland getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Highland?
If you're considering a spontaneous Highland trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Highland?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Highland.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will probably be the largest expense during your trip to Highland.
  3. Discover Highland with our trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Highland. You can also save your must-visit places, collaborate with friends and family and manage your plans in one place.
  4. Decide how many days away: Start by compiling a list of the sights and activities you want to get to in Highland. Then, estimate how long you'll need at each, along with any travel time.
  5. Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Highland vacation package for you.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on Highland's best offerings. Find all the exciting things to do in Highland with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Highland vacation packages?
If you're like us, you love traveling the world but don't love 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 total cost of your Highland break 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.