Search Cheap Flights toHighland
Search 400 airlines and 321,000 hotels worldwide.
Stop Planning & Start Exploring
FREE 24 hour cancellation on most flights
Highland Flights as Low as $63
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
















Cheap Flights to Highland
Fall in love at first flight with your vacation to Highland by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Highland on Hotwire, and you’ll be up, up, and on a getaway in no time.
Because once the wheels are down in Highland, the good times start rolling. So buckle up, you’re in for a fun ride.
Frequently Asked Questions About flights to Highland
Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Highland with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.
So all you have to worry about is where you’re headed after the RFD airport.
What is the cheapest month to fly to Highland?
Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Highland are in August, but when you book your flight on Hotwire, savings are always in season.
How many airlines fly to Highland?
Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Highland.
What airport is best to fly into Highland?
When you’re planning your trip to Highland, convenience is the name of the game. Luckily, Highland Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Highland must-do list.
How much are flights to Highland?
Got very cheap flights on your vacation itinerary? When you book your airline tickets to Highland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $63, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.
How to get cheap flights to Highland?
The trick to saving a stack of cash on your flight to Highland? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $63 right now, why wait?
Destination airport | O'Hare Intl. |
Destination airport IATA code | ORD |
Roundtrip price | $63 |
Last Minute Hotel Deals in Highland

Hilton Chicago/Oak Lawn
Reviewed on Jul 21, 2025

Ameristar Casino Hotel East Chicago
Reviewed on Jul 24, 2025

Quality Inn & Suites Orland Park - Chicago
Reviewed on Jul 23, 2025

Motel 6 - Chicago, IL
Reviewed on Jul 17, 2025

Spring House Inn
Reviewed on Jul 24, 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Reviewed on Jul 23, 2025

Super 8 by Wyndham South Holland
Reviewed on Jul 21, 2025

Baymont by Wyndham Chicago/Alsip
Reviewed on Jul 23, 2025
Nearby Cities
Popular Flight Routes
- Atlanta to New York
- Detroit to Las Vegas
- Dallas to Atlanta
- Dallas to Yosemite National Park
- Toronto to Edmonton
- Chicago to Tulum
- Houston to Lake Tahoe
- Chicago to Las Vegas
- Dallas to Miami
- Dallas to Lake Tahoe
- New York to Miami
- New York to Las Vegas
- Miami to Atlanta
- Minneapolis St Paul to Fort Walton Beach Destin
- Dallas to Branson
- Cleveland to Vero Beach
- Managua to Miami
- Atlanta to Boston
- Austin to Tulum
- Calgary to Vancouver
Flights to Our Favorite Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Myrtle Beach
- Flights to Chicago
- Flights to San Diego
- Flights to Panama City Beach
- Flights to Destin
- Flights to Ocean City
- Flights to Los Angeles
- Flights to Miami
- Flights to Boston
- Flights to Nashville
- Flights to Atlantic City
- Flights to Gulf Shores
- Flights to Pigeon Forge
Top Highland Hotels
- Hilton Chicago/Oak Lawn
- Ameristar Casino Hotel East Chicago
- Quality Inn & Suites Orland Park - Chicago
- EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
- Super 8 by Wyndham South Holland
- Baymont by Wyndham Chicago/Alsip
- La Quinta Inn & Suites by Wyndham Chicago Tinley Park
- Fairfield Inn and Suites By Marriott Merrillville
- DoubleTree by Hilton Chicago - Alsip
- FairBridge Inn Express Merrillville
- Baymont by Wyndham Portage Indiana Dunes
- Econo Lodge