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Highland

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Highland Flights as Low as $59

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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 April, 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 $59, 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 $59 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$58

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 ...
8.4/10 Very Good! (1,271 reviews)
Ok

Reviewed on Apr 5, 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 ...
9.4/10 Exceptional! (314 reviews)
All in all we had a wonderful stay

Reviewed on Apr 4, 2026

Wind Creek Southland Casino and Hotel
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 ...
9/10 Wonderful! (1,253 reviews)
It was quiet and pleasant for our stay

Reviewed on Apr 6, 2026

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Econo Lodge South Holland - Chicago Southland

Econo Lodge South Holland - Chicago Southland

2 out of 5
17301 S Halsted St, Building B South Holland IL
Stay at this hotel in South Holland. Enjoy free WiFi, free parking, and room service. Popular attractions Midwest Carvers Museum and Harvey Public Library are ...
6/10 (744 reviews)
Yes,my room was clean

Reviewed on Mar 17, 2026

Econo Lodge South Holland - Chicago Southland
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! (1,135 reviews)
Staff was very friendly.

Reviewed on Apr 5, 2026

Wingate by Wyndham Tinley Park
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 ...
8.8/10 Excellent! (1,003 reviews)
Very clean rooms very spacious and comfortable beds

Reviewed on Apr 4, 2026

Hyatt Place Chicago-South/University Medical Center
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 ...
8.2/10 Very Good! (1,073 reviews)
Room was clean. Shower was amazing. Staff were very helpful. WiFi was sufficient. Beds were horrible.

Reviewed on Apr 5, 2026

Baymont by Wyndham Chicago/Alsip
FairBridge Inn Express Merrillville

FairBridge Inn Express Merrillville

2 out of 5
8250 Louisiana Street Merrillville IN
Stay at this motel in Merrillville. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
7/10 Good! (582 reviews)
Great location, helpful staff, budget room

Reviewed on Apr 3, 2026

FairBridge Inn Express 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.