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Highland

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Highland Flights as Low as $62

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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 14 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 $62, 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 $62 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$62

Last Minute Hotel Deals in Highland

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! (1,003 reviews)
The room was spotless. The only thing wrong was the hot water in the shower hardly worked. They need to get that fixed.

Reviewed on Jan 21, 2026

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! (1,188 reviews)
Nice hotel

Reviewed on Jan 21, 2026

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! (228 reviews)
This hotel has it all for a cheap price. My room was like a 500 dollar a night room extra spacious bathroom was extremely big… my shower had big beautiful glass. And don’t forget my mirror that was the size of the door… you want to feel like you’re rich but pay a small price? Windcreek is the place ...

Reviewed on Jan 16, 2026

Wind Creek Southland Casino and Hotel
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 (1,001 reviews)
Yes

Reviewed on Jan 10, 2026

Motel 6 Hammond, IN - Chicago Area
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! (1,221 reviews)
Clean room,nice space

Reviewed on Jan 21, 2026

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Wingate by Wyndham Tinley Park

Wingate by Wyndham Tinley Park

2.5 out of 5
18421 N Creek Drive Tinley Park IL
Stay at this hotel in Tinley Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,084 reviews)
Yes

Reviewed on Jan 20, 2026

Wingate by Wyndham Tinley Park
Luxe Inn and Suites

Luxe Inn and Suites

2.5 out of 5
1335 E. SIBLEY BLVD. Dolton IL
Stay at this motel in Dolton. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Veterans Memorial Park and River Oaks Center are located ...
6.4/10 (448 reviews)
It was cool first room I couldn’t get in had to go back and forth in the cold 8 times before she switched the room the bathroom was ugly so I didn’t use it

Reviewed on Jan 26, 2026

Luxe Inn and Suites
La Quinta Inn & Suites by Wyndham Chicago Tinley Park

La Quinta Inn & Suites by Wyndham Chicago Tinley Park

3 out of 5
7255 West 183rd St. Tinley Park IL
Book a stay at this business-friendly hotel in Tinley Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.6/10 (1,008 reviews)
Yes

Reviewed on Jan 20, 2026

La Quinta Inn & Suites by Wyndham Chicago Tinley Park
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.