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Highland

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Highland Flights as Low as $63

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

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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 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?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

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 ...
8/10 Very Good! (1,022 reviews)
"The staff was extremely helpful in everything that we needed!"

Reviewed on Jul 21, 2025

Hilton Chicago/Oak Lawn
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 ...
8.4/10 Very Good! (1,023 reviews)
"Great"

Reviewed on Jul 24, 2025

Ameristar Casino Hotel East Chicago
Quality Inn & Suites Orland Park - Chicago

Quality Inn & Suites Orland Park - Chicago

2.5 out of 5
8800 W 159th St, Orland Park, IL
Book a stay at this business-friendly hotel in Orland Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.2/10 Good! (1,011 reviews)
"Good place to stay"

Reviewed on Jul 23, 2025

Quality Inn & Suites Orland Park - Chicago
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located nearby.
6/10 (46 reviews)
"I appreciate all the people that work at this motel 6! They are polite and always willing to help with reservations. I also have a service animal and it's been so peaceful to stay there."

Reviewed on Jul 17, 2025

Motel 6 - Chicago, IL
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,015 reviews)
"Nestled in the woods it was a nice place to stay. The room was very clean and the staff were very friendly."

Reviewed on Jul 24, 2025

Spring House Inn
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 ...
8.8/10 Excellent! (1,016 reviews)
Great room, super comfortable bed
"We came for a concert, and while we didn't spend much time at the hotel, the time we were there was excellent, very comfortable room, quality decor and toiletries, overall very nice."

Reviewed on Jul 23, 2025

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 ...
7.4/10 Good! (1,026 reviews)
"The room was comfortable, clean and quiet. The only problem I had was the hot water pressure was low in the sink."

Reviewed on Jul 21, 2025

Super 8 by Wyndham South Holland
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! (1,011 reviews)
"Clean comfortable room. Pleasant staff. Nothing fancy or upscale but met our traveling needs for a clean & comfortable room. Breakfast choices limited good coffee."

Reviewed on Jul 23, 2025

Baymont by Wyndham Chicago/Alsip
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.