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Highland

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Highland Flights as Low as $90

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

Spirit Airlines
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 7 hours ago
$90
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $90 found 7 hours ago
Frontier Airlines
Thu, May 29 - Sun, Jun 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, May 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Jun 1, priced at $100 found 3 days ago
Spirit Airlines
Tue, Jul 8 - Tue, Jul 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 12 hours ago
$100
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $100 found 12 hours ago
Frontier Airlines
Sat, Jun 14 - Sun, Jun 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$117 Roundtrip, found 18 hours ago
$117
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sat, Jun 14 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sun, Jun 15, priced at $117 found 18 hours ago
United
Tue, Aug 19 - Tue, Aug 26
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 Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 1 day ago
Delta
Tue, Aug 19 - Tue, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 1 day ago
American Airlines
Tue, Aug 19 - Tue, Aug 26
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 Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 1 day ago
Frontier Airlines
Tue, Jul 29 - Tue, Aug 5
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jul 29 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Aug 5, priced at $178 found 1 day ago
Frontier Airlines
Mon, Jul 28 - Fri, Aug 1
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jul 28 from Sky Harbor Intl. to O'Hare Intl., returning Fri, Aug 1, priced at $189 found 1 day ago
Delta
Tue, Jul 15 - Tue, Jul 15
DAL
Love Field
ORD
O'Hare Intl.
$194 Roundtrip, found 6 days ago
$194
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jul 15 from Love Field to O'Hare Intl., returning Tue, Jul 15, priced at $194 found 6 days ago
Delta
Sat, Jul 5 - Tue, Jul 15
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jul 5 from Love Field to Midway Intl., returning Tue, Jul 15, priced at $197 found 2 days ago
Contour Airlines
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$213 Roundtrip, found 7 hours ago
$213
Roundtrip
found 7 hours ago
Select Contour Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $213 found 7 hours ago
Alaska Airlines
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 7 hours ago
$216
Roundtrip
found 7 hours ago
Select Alaska Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $216 found 7 hours ago
Frontier Airlines
Thu, Aug 7 - Thu, Aug 14
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 7 from Sky Harbor Intl. to Midway Intl., returning Thu, Aug 14, priced at $227 found 1 day ago
Frontier Airlines
Sat, Jul 12 - Wed, Jul 16
LAX
Los Angeles Intl.
MDW
Midway Intl.
$248 Roundtrip, just found
$248
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jul 12 from Los Angeles Intl. to Midway Intl., returning Wed, Jul 16, priced at $248 just found
Sun Country Airlines
Fri, Jul 11 - Mon, Jul 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$286 Roundtrip, found 1 day ago
$286
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Fri, Jul 11 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $286 found 1 day 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 July, 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 $90, 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 $90 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$90

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! (1,002 reviews)
"Staff is lovely. I really enjoyed my stay!"

Reviewed on May 20, 2025

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Hilton Chicago/Oak Lawn
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! (1,000 reviews)
"We enjoyed our stay, the staff were very helpful and friendly. The only thing that could be improved is their parking lot, it's pretty bumpy and handicapped parking is limited."

Reviewed on May 20, 2025

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EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
DoubleTree by Hilton Chicago - Alsip
DoubleTree by Hilton Chicago - Alsip
4 out of 5
5000 W 127th St, Alsip, IL
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! (1,001 reviews)
"No issues, 20 min from MDW Airport, clean, quiet, service desk support was excellent"

Reviewed on May 21, 2025

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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
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)
Services at front desk and breakfast are excellent
"Very clean and well-maintained room but the A/C is noisy and annoying."

Reviewed on May 21, 2025

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Hyatt Place Chicago-South/University Medical Center
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! (1,002 reviews)
"It was close to everything you need even the casino."

Reviewed on May 20, 2025

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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! (1,001 reviews)
Just my experience
"The hotel and rooms are really clean. I just found the staff a little rude. Housekeeping just walked in my room without knocking and it was not even check out time. Whenever i went down to the front desk i always had to wait at least 7 to 8 minutes before anyone came out. The weekend manager was ..."

Reviewed on May 18, 2025

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Baymont by Wyndham Chicago/Alsip
Red Roof Inn Chicago - Lansing
Red Roof Inn Chicago - Lansing
2 out of 5
2450 East 173rd Street, Lansing, IL
Stay at this hotel in Lansing. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Lansing Square Shopping Center and River Oaks Center ...
4.4/10 (1,002 reviews)
"No problems"

Reviewed on May 19, 2025

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Red Roof Inn Chicago - Lansing
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 ...
9.2/10 Wonderful! (1,001 reviews)
"Sarah at the front desk was super nice"

Reviewed on May 22, 2025

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Wingate by Wyndham Tinley Park
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.