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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
Wed, Feb 26 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Feb 26 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Mar 4, priced at $58 found 2 hours ago
Frontier Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 5 hours ago
$63
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $63 found 5 hours ago
Frontier Airlines
Tue, Feb 18 - Tue, Feb 25
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$63 Roundtrip, found 4 days ago
$63
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Feb 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Feb 25, priced at $63 found 4 days ago
Frontier Airlines
Wed, Jan 22 - Tue, Jan 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 6 hours ago
$68
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Jan 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jan 28, priced at $68 found 6 hours ago
Frontier Airlines
Tue, Mar 4 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 11 hours ago
$73
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Mar 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 4, priced at $73 found 11 hours ago
Spirit Airlines
Wed, Jan 22 - Tue, Jan 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$113 Roundtrip, found 6 hours ago
$113
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, Jan 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jan 28, priced at $113 found 6 hours ago
Frontier Airlines
Thu, Jan 9 - Mon, Jan 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$118 Roundtrip, found 11 hours ago
$118
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, Jan 9 from George Bush Intercontinental to O'Hare Intl., returning Mon, Jan 13, priced at $118 found 11 hours ago
Spirit Airlines
Wed, Jan 29 - Thu, Jan 30
BOS
Logan Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jan 29 from Logan Intl. to O'Hare Intl., returning Thu, Jan 30, priced at $119 found 2 days ago
Delta
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 5 hours ago
$132
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 5 hours ago
American Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 5 hours ago
$132
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 5 hours ago
United
Wed, Feb 12 - Sat, Feb 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 5 hours ago
$137
Roundtrip
found 5 hours ago
Select United flight, departing Wed, Feb 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Feb 15, priced at $137 found 5 hours ago
JetBlue Airways
Wed, Jan 29 - Thu, Jan 30
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Jan 29 from Logan Intl. to O'Hare Intl., returning Thu, Jan 30, priced at $157 found 2 days ago
Frontier Airlines
Fri, Jan 10 - Sun, Jan 12
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 10 from Ronald Reagan Washington National to O'Hare Intl., returning Sun, Jan 12, priced at $165 found 1 day ago
Frontier Airlines
Tue, Dec 31 - Tue, Jan 7
BOS
Logan Intl.
MDW
Midway Intl.
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Dec 31 from Logan Intl. to Midway Intl., returning Tue, Jan 7, priced at $188 found 2 days ago
Frontier Airlines
Fri, Jan 10 - Sun, Jan 12
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 10 from Ronald Reagan Washington National to Midway Intl., returning Sun, Jan 12, priced at $199 found 1 day ago
Frontier Airlines
Wed, Dec 25 - Tue, Dec 31
IAH
George Bush Intercontinental
MDW
Midway Intl.
$438 Roundtrip, found 3 days ago
$438
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Dec 25 from George Bush Intercontinental to Midway Intl., returning Tue, Dec 31, priced at $438 found 3 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 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
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$68

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 1 to Jan 2
$128
includes taxes & fees
Jan 1 - Jan 2, 2025
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! (1,004 reviews)
"The only drawback was that the hotel charges $10 for parking and doesn't tell you about it when you're checking in. We didn't know about it until we got our bill at checkout. A little late then to park somewhere else or at least know about it. I thought that was rather nontransparent on their ..."

Reviewed on Dec 17, 2024

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 $124 per night from Jan 5 to Jan 6
$124
includes taxes & fees
Jan 5 - Jan 6, 2025
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)
"Great stay. Nice room."

Reviewed on Dec 13, 2024

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 $62 per night from Dec 29 to Dec 30
$62
includes taxes & fees
Dec 29 - Dec 30
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! (1,006 reviews)
You get what you paid for
"Property was clean. Room was of good size. Bathroom was small compared to overall room. Bed was somewhat comfortable. They offer a very small breakfast (2 types of cereal and toast, milk and juice). Very close to the new casino, however, not in the best of areas. Customer service needs some work ..."

Reviewed on Dec 21, 2024

Super 8 by Wyndham South Holland
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 $149 per night from Dec 30 to Dec 31
$149
includes taxes & fees
Dec 30 - Dec 31
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 ...
8.6/10 Excellent! (1,001 reviews)
"Very full service with excellent parking underground"

Reviewed on Dec 21, 2024

Hyatt Place Chicago-South/University Medical Center
Sophy Hyde Park
Sophy Hyde Park
4 out of 5
1411 East 53rd Street, Chicago, IL
The price is $196 per night from Jan 3 to Jan 4
$196
includes taxes & fees
Jan 3 - Jan 4, 2025
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our ...
9.4/10 Exceptional! (879 reviews)
"it was a beautiful room"

Reviewed on Dec 19, 2024

Sophy Hyde Park
La Quinta Inn & Suites by Wyndham Chicago Tinley Park
La Quinta Inn & Suites by Wyndham Chicago Tinley Park
2.5 out of 5
7255 West 183rd St., Tinley Park, IL
The price is $67 per night from Jan 5 to Jan 6
$67
includes taxes & fees
Jan 5 - Jan 6, 2025
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 ...
6.2/10 (1,003 reviews)
"They had a good breakfast. The room was clean and the staff was very friendly."

Reviewed on Dec 17, 2024

La Quinta Inn & Suites by Wyndham Chicago Tinley Park
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 $80 per night from Dec 24 to Dec 25
$80
includes taxes & fees
Dec 24 - Dec 25
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 (1,003 reviews)
"Stayed here for one night on our way to Chicago. Overall, your normal mid-tier hotel experience. Staff was nice, the occasionally weed smell in the elevator, breakfast was pretty good, and normal west and tear of a hotel room but it was clean. Overall a solid hotel choice!"

Reviewed on Dec 22, 2024

Country Inn & Suites by Radisson, Merrillville, IN
Ameristar Casino Hotel East Chicago
Ameristar Casino Hotel East Chicago
4 out of 5
777 Ameristar Blvd., East Chicago, IN
The price is $156 per night from Jan 22 to Jan 23
$156
includes taxes & fees
Jan 22 - Jan 23, 2025
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)
"Excellent service"

Reviewed on Dec 16, 2024

Ameristar Casino Hotel East Chicago
See all 729 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.