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Highland

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Highland Flights as Low as $213

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Hawaiian Airlines
Delta

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 February, 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 3 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 $213, 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 $213 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$213

Last Minute Hotel Deals in Highland

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 ...
6.8/10 (208 reviews)
The handle for the sink wasn’t put on properly making it difficult to turn the water on. Otherwise everything was great.

Reviewed on Dec 17, 2025

Motel 6 - Chicago, IL
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,012 reviews)
Ok

Reviewed on Dec 22, 2025

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
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 ...
8.2/10 Very Good! (1,150 reviews)
The room was clean. Bathroom could use some attention in the toilet area

Reviewed on Dec 22, 2025

Hilton Chicago/Oak Lawn
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St Hazel Crest IL
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe ...
9.2/10 Wonderful! (209 reviews)
the room was clean and beautiful. The staff was pleasant and helpful. We enjoyed every minute of our visit.

Reviewed on Dec 20, 2025

Wind Creek Southland Casino and Hotel
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 ...
8/10 Very Good! (1,004 reviews)
Dry friendly and fast check in. Lobby clean and modern. Easy parking.

Reviewed on Dec 19, 2025

Baymont by Wyndham Chicago/Alsip
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
Book a stay at this business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,177 reviews)
Staff was courteous, amenities excellent, clean.

Reviewed on Dec 19, 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Motel 6 Hammond, IN - Chicago Area

Motel 6 Hammond, IN - Chicago Area

2 out of 5
3840 179th St Hammond IN
Stay at this motel in Hammond. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.2/10 (1,005 reviews)
They could use some bigger beds but not bad

Reviewed on Dec 21, 2025

Motel 6 Hammond, IN - Chicago Area
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3 out of 5
5225 S Harper Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,003 reviews)
My grandson and I stayed one night after my husband’s surgery at the University of Chicago Hospital. We had a wonderful stay. The room was spotless, comfortable, and the staff was very helpful.

Reviewed on Dec 19, 2025

Hyatt Place Chicago-South/University Medical Center
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.