Title: Highland Vacation Packages 2026 from $325 | Expedia.com [Highland Travel Guide](https://expedia.com/Highland.dx177657)[Hotels in Highland](https://expedia.com/Highland-Hotels.d177657.Travel-Guide-Hotels)[Vacation Rentals in Highland](https://expedia.com/Highland-Vacation-Rentals.d177657.Travel-Guide-VacationRentals)[Flights to Highland](https://expedia.com/Cheap-Flights-To-Highland.d177657.Travel-Guide-Flights)[Things to do in Highland](https://expedia.com/Things-To-Do-In-Highland.d177657.Travel-Guide-Activities)[Car Rentals in Highland](https://expedia.com/Car-Rentals-In-Highland.d177657.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highland Vacations from $325 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Hard-Rock-Casino-Northern-Indiana-Gary.d689582177477787648.Vacation-Attraction), [Purdue University Northwest](https://www.expedia.com/Purdue-University-Northwest-Hammond.d553248622008968181.Vacation-Attraction) and [Hammond Sportsplex & Community Center](https://www.expedia.com/Hammond-Sportsplex-Community-Center-Hammond.d620049903162130432.Vacation-Attraction) 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. ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago $325 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.2/10 Very Good! (2,365 reviews) Room neat, clean and cozy. Check in was easy. Small and intimate for quick weekend getaway. Reviewed on Feb 16, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago $332 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Wonderful stay. Second time there and would happily stay again when visiting that area of Chicago. Reviewed on Feb 19, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago $513 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (380 reviews) First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon! Reviewed on Feb 19, 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago $452 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Nice hotel Great location Reviewed on Feb 15, 2026 ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago $414 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,862 reviews) Excellent customer service from Security to Front Desk ,Restaurant,cleanliness ,best amenities Reviewed on Feb 16, 2026 Don't see what you're looking for? See all available trips from Columbus to Highland [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-19/2026-03-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_177657) ## Highland Hotel Deals ![Hilton Chicago/Oak Lawn](https://images.trvl-media.com/lodging/1000000/20000/17700/17618/6279b55c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Oak Lawn 9333 S Cicero Ave Oak Lawn IL Fully refundableReserve now, pay when you stay $110 nightly $126 total Feb 26 - Feb 27 Total with taxes and fees 8.4/10 Very Good! (1,220 reviews) I stayed 2 non-cosecutive nights snd it wss a huge hassel getting Experion's software to understand that. The Hilton was great. Efficient, friendly, helpful. Rooms (I stayed in 2 different ones) were clean and compfy. Shuttle service to Midway Airport was timely The shuttle wasn't running last 1pm ... Reviewed on Feb 18, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F26%2F2026&endDate=2%2F27%2F2026&selected=17618&PinnedHotelID=17618&HadPinnedHotel=true®ionId=177657) ![DoubleTree by Hilton Chicago - Alsip](https://images.trvl-media.com/lodging/1000000/30000/25600/25507/fcb66f28_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Chicago - Alsip 5000 W 127th St Alsip IL Fully refundableReserve now, pay when you stay $102 nightly $115 total Mar 1 - Mar 2 Total with taxes and fees 8.4/10 Very Good! (1,003 reviews) When showering the water was warm not hot at all Reviewed on Feb 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=25507&PinnedHotelID=25507&HadPinnedHotel=true®ionId=177657) ![Econo Lodge South Holland - Chicago Southland](https://images.trvl-media.com/lodging/1000000/10000/4000/3986/72bd041c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Econo Lodge South Holland - Chicago Southland 17301 S Halsted St, Building B South Holland IL Fully refundableReserve now, pay when you stay $54 nightly $61 total Mar 22 - Mar 23 Total with taxes and fees 5.8/10 (718 reviews) Good Reviewed on Feb 16, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=3986&PinnedHotelID=3986&HadPinnedHotel=true®ionId=177657) [See all 921 properties in Highland](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F20%2F2026&endDate=2%2F21%2F2026®ionId=177657) 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](https://www.expedia.com/Whihala-Beach-Whiting.d553248635983991660.Vacation-Attraction), [Lake Street Beach](https://www.expedia.com/Lake-Street-Beach-Indiana.d553248635983994013.Vacation-Attraction) and [Theatre at the Center](https://www.expedia.com/Theatre-At-The-Center-Munster.d553248634329241866.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Highland vacation package cost? ### What are the cheapest months to go to Highland? ### How many days is enough for Highland? ### How to find the best Highland package deals? ### Is it cheaper to book a Highland vacation as a package? ### When to book a vacation package to Highland? ### 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](https://www.expedia.com/why/trip-planning): 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](https://www.expedia.com/Things-To-Do-In-Highland.d177657.Travel-Guide-Activities) with our dedicated travel guide. ### Does Expedia offer Book Now, Pay Later Highland vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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