Search Cheap Flights to
Highland

Photo by Joe Farmer

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.

Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
United
American Airlines
Frontier Airlines
Delta
Frontier Airlines
Bargain Flight
JetBlue Airways
KEY LIME AIR DBA DENVER AIR CONNECTION

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 September, 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 15 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?

Highland Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$164

Last Minute Hotel Deals in Highland

Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
Hilton Chicago/Oak Lawn
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
12801 South Cicero, Alsip, IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Baymont by Wyndham Chicago/Alsip
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located ...
Motel 6 - Chicago, IL
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St, Hazel Crest, IL
Stay at this 4-star spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe ...
Wind Creek Southland Casino and Hotel
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Stay at this 4-star beach hotel in East Chicago. Enjoy 5 restaurants, a marina, and a casino. Our guests praise the helpful staff and the clean rooms in our ...
Ameristar Casino Hotel East Chicago
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

3.5 out of 5
18501 Convention Center Drive, Tinley Park, IL
Stay at this 3.5-star business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Super 8 by Wyndham South Holland

Super 8 by Wyndham South Holland

2 out of 5
17225 Halsted St, South Holland, IL
Book a stay at this business-friendly hotel in South Holland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Super 8 by Wyndham South Holland
Fairfield Inn and Suites By Marriott Merrillville

Fairfield Inn and Suites By Marriott Merrillville

2.5 out of 5
8275 Georgia St, Merrillville, IN
Book a stay at this business-friendly hotel in Merrillville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Fairfield Inn and Suites By Marriott Merrillville
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.