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Highland

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Highland Flights as Low as $58

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

Frontier Airlines
Tue, Feb 25 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 4 days ago
$58
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Feb 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Mar 4, priced at $58 found 4 days ago
Frontier Airlines
Wed, Feb 26 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $58 found 1 day ago
Frontier Airlines
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 6 days ago
$63
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $63 found 6 days ago
Frontier Airlines
Sat, Mar 1 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Mar 1 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $63 found 1 day ago
Frontier Airlines
Tue, Feb 11 - Wed, Feb 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 21 hours ago
$68
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Tue, Feb 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Feb 19, priced at $68 found 21 hours ago
Spirit Airlines
Wed, Mar 5 - Wed, Mar 12
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$70 Roundtrip, found 5 days ago
$70
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Mar 5 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Mar 12, priced at $70 found 5 days ago
Frontier Airlines
Fri, Jan 31 - Sun, Feb 2
MCO
Orlando Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 12 hours ago
$94
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Jan 31 from Orlando Intl. to O'Hare Intl., returning Sun, Feb 2, priced at $94 found 12 hours ago
Spirit Airlines
Wed, Feb 5 - Thu, Feb 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 7 hours ago
$97
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, Feb 5 from Los Angeles Intl. to O'Hare Intl., returning Thu, Feb 6, priced at $97 found 7 hours ago
Frontier Airlines
Wed, Feb 12 - Tue, Feb 25
MCO
Orlando Intl.
MDW
Midway Intl.
$119 Roundtrip, found 12 hours ago
$119
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, Feb 12 from Orlando Intl. to Midway Intl., returning Tue, Feb 25, priced at $119 found 12 hours ago
Delta
Wed, Mar 19 - Wed, Mar 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 6 days ago
$134
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Mar 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 19, priced at $134 found 6 days ago
United
Sat, Mar 1 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select United flight, departing Sat, Mar 1 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $137 found 1 day ago
American Airlines
Sat, Mar 1 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 1 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $137 found 1 day ago
Frontier Airlines
Sun, Feb 2 - Mon, Feb 10
LAX
Los Angeles Intl.
MDW
Midway Intl.
$140 Roundtrip, found 3 days ago
$140
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Feb 2 from Los Angeles Intl. to Midway Intl., returning Mon, Feb 10, priced at $140 found 3 days ago
JetBlue Airways
Tue, Apr 15 - Wed, Apr 23
MCO
Orlando Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 14 hours ago
$197
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Apr 15 from Orlando Intl. to O'Hare Intl., returning Wed, Apr 23, priced at $197 found 14 hours ago
Alaska Airlines
Wed, Feb 5 - Thu, Feb 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$323 Roundtrip, found 7 hours ago
$323
Roundtrip
found 7 hours ago
Select Alaska Airlines flight, departing Wed, Feb 5 from Los Angeles Intl. to O'Hare Intl., returning Thu, Feb 6, priced at $323 found 7 hours ago
Delta
Sat, Jan 25 - Sat, Feb 1
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$393 Roundtrip, found 10 hours ago
$393
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Jan 25 from Newark Liberty Intl. Airport to Midway Intl., returning Sat, Feb 1, priced at $393 found 10 hours 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 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 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 $58, 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 $58 right now, why wait?

Highland Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
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
The price is $128 per night from Jan 29 to Jan 30
$128
includes taxes & fees
Jan 29 - Jan 30
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 ...
7.8/10 Good! (1,000 reviews)
"Hotel was not bad. Bathroom size a little awkward, and everything costs extra; except water as they have a filling station. If breakfast pricing, at $26 per, wasn’t so ridiculous my review would have been better. But free transport to the airport was pretty damn nice."

Reviewed on Jan 20, 2025

Hilton Chicago/Oak Lawn
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 $143 per night from Jan 28 to Jan 29
$143
includes taxes & fees
Jan 28 - Jan 29
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! (1,000 reviews)
"Nice hotel. Easy parking. Lots of food options. Hotel staff went out of their way to make us comfortable. Would stay here again."

Reviewed on Jan 20, 2025

Hyatt Place Chicago-South/University Medical Center
DoubleTree by Hilton Chicago - Alsip
DoubleTree by Hilton Chicago - Alsip
4 out of 5
5000 W 127th St, Alsip, IL
The price is $114 per night from Jan 29 to Jan 30
$114
includes taxes & fees
Jan 29 - Jan 30
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! (1,000 reviews)
"The location and cookies of course. They just need to have cookies available for guest at all times."

Reviewed on Jan 1, 2025

DoubleTree by Hilton Chicago - Alsip
Super 8 by Wyndham South Holland
Super 8 by Wyndham South Holland
2 out of 5
17225 Halsted St, South Holland, IL
The price is $66 per night from Jan 24 to Jan 25
$66
includes taxes & fees
Jan 24 - Jan 25
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! (1,007 reviews)
"Great staff"

Reviewed on Jan 17, 2025

Super 8 by Wyndham South Holland
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 $87 per night from Feb 9 to Feb 10
$87
includes taxes & fees
Feb 9 - Feb 10
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 (1,001 reviews)
"Excellent!"

Reviewed on Jan 21, 2025

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 $104 per night from Jan 26 to Jan 27
$104
includes taxes & fees
Jan 26 - Jan 27
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! (1,000 reviews)
"It was a nice hotel for what we needed for a quick overnight!"

Reviewed on Jan 19, 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr, an IHG Hotel
Quality Inn & Suites Matteson near I-57
Quality Inn & Suites Matteson near I-57
2.5 out of 5
21050 Matteson Avenue, Matteson, IL
The price is $82 per night from Jan 26 to Jan 27
$82
includes taxes & fees
Jan 26 - Jan 27
Stay at this hotel in Matteson. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hollywood Casino Amphitheatre and Credit Union 1 Amphitheatre ...
6.2/10 (1,001 reviews)
"It’s just ok. Nothing spectacular but still a very livable space."

Reviewed on Jan 19, 2025

Quality Inn & Suites Matteson near I-57
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 $85 per night from Feb 9 to Feb 10
$85
includes taxes & fees
Feb 9 - Feb 10
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! (1,002 reviews)
"Good breakfast, friendly staff"

Reviewed on Jan 22, 2025

Quality Inn & Suites Orland Park - Chicago
See all 723 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.