Search Cheap Flights to
Highland

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Highland Flights as Low as $98

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

Frontier Airlines
Thu, Dec 12 - Tue, Dec 17
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Dec 12 from Sky Harbor Intl. to O'Hare Intl., returning Tue, Dec 17, priced at $98 found 1 day ago
Frontier Airlines
Thu, Nov 21 - Mon, Nov 25
MCO
Orlando Intl.
MDW
Midway Intl.
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Nov 21 from Orlando Intl. to Midway Intl., returning Mon, Nov 25, priced at $108 found 3 days ago
Spirit Airlines
Fri, Dec 6 - Sun, Dec 8
MCO
Orlando Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Fri, Dec 6 from Orlando Intl. to O'Hare Intl., returning Sun, Dec 8, priced at $117 found 13 hours ago
Frontier Airlines
Fri, Dec 6 - Sun, Dec 8
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Dec 6 from Sky Harbor Intl. to O'Hare Intl., returning Sun, Dec 8, priced at $118 found 3 days ago
Frontier Airlines
Thu, Nov 21 - Sun, Nov 24
MCO
Orlando Intl.
MDW
Midway Intl.
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Nov 21 from Orlando Intl. to Midway Intl., returning Sun, Nov 24, priced at $119 found 3 days ago
Spirit Airlines
Thu, Dec 12 - Tue, Dec 17
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Dec 12 from Sky Harbor Intl. to O'Hare Intl., returning Tue, Dec 17, priced at $120 found 1 day ago
Frontier Airlines
Fri, Jan 17 - Thu, Jan 23
MSY
Louis Armstrong New Orleans Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jan 17 from Louis Armstrong New Orleans Intl. to O'Hare Intl., returning Thu, Jan 23, priced at $128 found 2 days ago
Frontier Airlines
Wed, Dec 4 - Fri, Dec 6
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Dec 4 from Sky Harbor Intl. to Midway Intl., returning Fri, Dec 6, priced at $138 found 1 day ago
American Airlines
Tue, Jan 14 - Tue, Jan 21
MCO
Orlando Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jan 14 from Orlando Intl. to O'Hare Intl., returning Tue, Jan 21, priced at $157 found 3 days ago
United
Fri, Jan 17 - Mon, Jan 20
MSY
Louis Armstrong New Orleans Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select United flight, departing Fri, Jan 17 from Louis Armstrong New Orleans Intl. to O'Hare Intl., returning Mon, Jan 20, priced at $189 found 2 days ago
Delta
Wed, Dec 11 - Wed, Dec 11
MCO
Orlando Intl.
MDW
Midway Intl.
$191 Roundtrip, found 6 days ago
$191
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Dec 11 from Orlando Intl. to Midway Intl., returning Wed, Dec 11, priced at $191 found 6 days ago
Frontier Airlines
Sun, Nov 24 - Thu, Nov 28
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$236 Roundtrip, found 17 hours ago
$236
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sun, Nov 24 from Louis Armstrong New Orleans Intl. to Midway Intl., returning Thu, Nov 28, priced at $236 found 17 hours ago
JetBlue Airways
Tue, Jan 14 - Tue, Jan 21
MCO
Orlando Intl.
ORD
O'Hare Intl.
$264 Roundtrip, found 3 days ago
$264
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Jan 14 from Orlando Intl. to O'Hare Intl., returning Tue, Jan 21, priced at $264 found 3 days ago
Alaska Airlines
Thu, Dec 5 - Mon, Dec 9
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$268 Roundtrip, found 3 days ago
$268
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Dec 5 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Dec 9, priced at $268 found 3 days ago
American Airlines
Wed, Dec 18 - Sat, Jan 4
MLU
Monroe Regional
ORD
O'Hare Intl.
$288 Roundtrip, found 3 days ago
$288
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Dec 18 from Monroe Regional to O'Hare Intl., returning Sat, Jan 4, priced at $288 found 3 days ago
Delta
Mon, Nov 25 - Tue, Dec 3
MLU
Monroe Regional
MDW
Midway Intl.
$328 Roundtrip, found 4 days ago
$328
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Nov 25 from Monroe Regional to Midway Intl., returning Tue, Dec 3, priced at $328 found 4 days ago

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 December, 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 $98, 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 $98 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$98

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 ...
7.6/10 Good! (1,005 reviews)
"-"

Reviewed on Nov 9, 2024

Get rates
Hilton Chicago/Oak Lawn
DoubleTree by Hilton Chicago - Alsip
DoubleTree by Hilton Chicago - Alsip
4 out of 5
5000 W 127th St, Alsip, IL
The price is $126 per night from Nov 18 to Nov 19
$126
includes taxes & fees
Nov 18 - Nov 19
Stay at this 4-star business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,004 reviews)
"Best hotel in the area!"

Reviewed on Nov 9, 2024

DoubleTree by Hilton Chicago - Alsip
Hyatt Place Chicago-South/University Medical Center
Hyatt Place Chicago-South/University Medical Center
3 out of 5
5225 S Harper Ave, Chicago, IL
The price is $158 per night from Nov 24 to Nov 25
$158
includes taxes & fees
Nov 24 - Nov 25
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (1,003 reviews)
"Met all of our needs. Great breakfast options!"

Reviewed on Nov 15, 2024

Hyatt Place Chicago-South/University Medical Center
Quality Inn & Suites Orland Park - Chicago
Quality Inn & Suites Orland Park - Chicago
2.5 out of 5
8800 W 159th St, Orland Park, IL
The price is $89 per night from Dec 1 to Dec 2
$89
includes taxes & fees
Dec 1 - Dec 2
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! (984 reviews)
"Well clean the staff is friendly everything is beautiful"

Reviewed on Nov 8, 2024

Quality Inn & Suites Orland Park - Chicago
Country Inn & Suites by Radisson, Merrillville, IN
Country Inn & Suites by Radisson, Merrillville, IN
3 out of 5
8311 Ohio, Merrillville, IN
The price is $76 per night from Dec 1 to Dec 2
$76
includes taxes & fees
Dec 1 - Dec 2
Stay at this 3-star business-friendly hotel in Merrillville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
6.6/10 (1,004 reviews)
Good pick
"Very friendly staff, good price and clean. Water pressure was kinda low but overall definitely recommend!"

Reviewed on Nov 12, 2024

Country Inn & Suites by Radisson, Merrillville, IN
EVEN Hotel Chicago Tinley Park-Conv Ctr, an IHG Hotel
EVEN Hotel Chicago Tinley Park-Conv Ctr, an IHG Hotel
3.5 out of 5
18501 Convention Center Drive, Tinley Park, IL
The price is $113 per night from Dec 8 to Dec 9
$113
includes taxes & fees
Dec 8 - Dec 9
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 ...
8.6/10 Excellent! (1,001 reviews)
"Very nice cozy place"

Reviewed on Nov 13, 2024

EVEN Hotel Chicago Tinley Park-Conv Ctr, an IHG Hotel
Sleep Inn Tinley Park I-80 near Amphitheatre-Convention Center
Sleep Inn Tinley Park I-80 near Amphitheatre-Convention Center
2.5 out of 5
18420 Spring Creek Dr, Tinley Park, IL
The price is $78 per night from Dec 11 to Dec 12
$78
includes taxes & fees
Dec 11 - Dec 12
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 ...
8.2/10 Very Good! (1,006 reviews)
"Updated & clean"

Reviewed on Nov 13, 2024

Sleep Inn Tinley Park I-80 near Amphitheatre-Convention Center
Ameristar Casino Hotel East Chicago
Ameristar Casino Hotel East Chicago
4 out of 5
777 Ameristar Blvd., East Chicago, IN
The price is $135 per night from Nov 18 to Nov 19
$135
includes taxes & fees
Nov 18 - Nov 19
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! (1,001 reviews)
"Overall very nice"

Reviewed on Nov 10, 2024

Ameristar Casino Hotel East Chicago
See all 718 properties in Highland
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.