Highland, IN

Travel Guide

A two-story brick building with a balcony, a front door, and steps leading up to the entrance.
The Cardinal Hotel

The Cardinal Hotel

3 out of 5
2205 Main St Highland IN
$248 nightly
The price is $277 total per night from Oct 24 to Oct 25
$277 total
Oct 24 - Oct 25
Total with taxes and fees
Stay at this hotel in Highland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hoosier Prairie and Centennial Park are located ...
10/10 Exceptional! (7 reviews)
"I had a great stay at this hotel! It’s only about a month old, so everything is brand new, clean, and feels fresh. The building itself is beautiful, and the rooms and bathrooms are especially impressive. The bathrooms are spacious, modern, and really well done. The only downside I noticed was the ..."

Reviewed on Sep 22, 2026

The Cardinal Hotel
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
$169 nightly
The price is $199 total per night from Sep 24 to Sep 25
$199 total
Sep 24 - Sep 25
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
7/10 Good! (1,006 reviews)
"My stay at the Chicago Lake Shore Hotel was good! The outside of the facility looks to be in rough shape but once you step inside the rooms they are updated and very clean!!! I would stay here again for the price. Of they could update/renovate the outside this place would be 10/10!!!"

Reviewed on Sep 22, 2026

Chicago Lake Shore Hotel
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4.5 out of 5
17300 S Halsted St Hazel Crest IL
$163 nightly
The price is $183 total per night from Oct 22 to Oct 23
$183 total
Oct 22 - Oct 23
Total with taxes and fees
Book a stay at this luxury resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Ravisloe Country Club and Oak Hill ...
9.4/10 Exceptional! (709 reviews)
"Puts you in mind of a Las Vegas Hotel everyone was very curious and engaging I felt welcomed from the moment I arrived...My room was very cozy and clean shower was definitely 5⭐️....only thing is they need better mattresses. Casino floor was very inviting had new games that actually payout... also ..."

Reviewed on Sep 23, 2026

Wind Creek Southland Casino and Hotel
See all 914 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.
2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking

Portage IN
Stay at this apartment in Portage. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Founders' Square Park ...
2 Full Bed | Non-Smoking
Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago

Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago

Chicago IL
Stay at this condo in Chicago. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Soldier Field and Griffin Museum of Science and Industry ...
8.4/10 Very Good! (6 reviews)
"We were satisfied with this place. It was close to the thing we came to visit. Parking was convenient. It was quiet with comfortable beds. Our only surprise was that it was on two levels"

Reviewed on Sep 21, 2026

Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago
Your Home Away From Home in Sauk Village

Your Home Away From Home in Sauk Village

Sauk Village IL
Stay at this vacation home in Sauk Village. Popular attractions Centennial Park and Community Veterans Memorial are located nearby.
7.4/10 Good! (10 reviews)
"Clean and just as described"

Reviewed on Sep 3, 2026

Your Home Away From Home in Sauk Village
See all 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.

Frequently asked questions

When is the best time to visit Highland?
The best time to visit Highland is from May through September, when the climate is most favorable for travelers. For fewer crowds and better value, the quieter months of December through March are a good option, offering a cooler experience during the winter season.
What cuisines can you find in Highland?
In Highland you can find German cuisine, with dishes like bratwurst, schnitzel, and sauerkraut. Travelers can also enjoy Italian, North American, and Latin American options, including Mexican food like tacos. Asian choices such as Chinese, Japanese, and Vietnamese are available, along with Mediterranean dishes.
Can I book a refundable hotel in Highland?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Highland by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Highland with Expedia?
Expedia makes it easier to plan your Highland trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Highland?
The best choice depends on your travel style. Hotels in Highland can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Highland trip on Expedia?
Once you've booked your Highland trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Highland trip?
Expedia offers customer support before, during, and after your Highland trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Highland?
If it's your first trip to Highland, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Highland hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Highland hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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