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Highland

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Highland Flights as Low as $96

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

Spirit Airlines
Wed, May 14 - Sat, May 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, May 14 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 17, priced at $96 found 2 days ago
Frontier Airlines
Sun, May 25 - Thu, May 29
BNA
Nashville Intl.
ORD
O'Hare Intl.
$101 Roundtrip, found 4 days ago
$101
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, May 25 from Nashville Intl. to O'Hare Intl., returning Thu, May 29, priced at $101 found 4 days ago
Frontier Airlines
Thu, May 22 - Thu, May 29
BNA
Nashville Intl.
ORD
O'Hare Intl.
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, May 22 from Nashville Intl. to O'Hare Intl., returning Thu, May 29, priced at $105 found 4 days ago
American Airlines
Wed, Jun 18 - Thu, Jun 19
BNA
Nashville Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 5 days ago
$147
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Jun 18 from Nashville Intl. to O'Hare Intl., returning Thu, Jun 19, priced at $147 found 5 days ago
Spirit Airlines
Sat, May 3 - Mon, May 5
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, May 3 from Sky Harbor Intl. to O'Hare Intl., returning Mon, May 5, priced at $152 found 1 day ago
United
Tue, Jun 17 - Wed, Jun 18
BNA
Nashville Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 5 days ago
$158
Roundtrip
found 5 days ago
Select United flight, departing Tue, Jun 17 from Nashville Intl. to O'Hare Intl., returning Wed, Jun 18, priced at $158 found 5 days ago
Delta
Tue, Jun 17 - Sat, Jun 21
BNA
Nashville Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 5 days ago
$178
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jun 17 from Nashville Intl. to O'Hare Intl., returning Sat, Jun 21, priced at $178 found 5 days ago
Frontier Airlines
Tue, Apr 29 - Sat, May 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Apr 29 from Los Angeles Intl. to Midway Intl., returning Sat, May 3, priced at $188 found 1 day ago
Frontier Airlines
Thu, May 1 - Sun, May 11
BNA
Nashville Intl.
MDW
Midway Intl.
$193 Roundtrip, found 21 hours ago
$193
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Thu, May 1 from Nashville Intl. to Midway Intl., returning Sun, May 11, priced at $193 found 21 hours ago
Frontier Airlines
Mon, Apr 21 - Tue, Apr 22
ONT
Los Angeles - Ontario Intl.
MDW
Midway Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Apr 21 from Los Angeles - Ontario Intl. to Midway Intl., returning Tue, Apr 22, priced at $198 found 1 day ago
Frontier Airlines
Wed, Apr 23 - Sat, Apr 26
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Apr 23 from Sky Harbor Intl. to Midway Intl., returning Sat, Apr 26, priced at $209 found 3 days ago
Bargain Flight
Tue, Apr 29 - Wed, May 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Apr 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 7, priced at $230 found 2 days ago
Frontier Airlines
Mon, Apr 28 - Thu, May 1
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$231 Roundtrip, found 4 days ago
$231
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Apr 28 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Thu, May 1, priced at $231 found 4 days ago
Hawaiian Airlines
Thu, Oct 2 - Tue, Oct 7
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$287 Roundtrip, found 4 days ago
$287
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Thu, Oct 2 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Tue, Oct 7, priced at $287 found 4 days ago
Sun Country Airlines
Fri, Oct 10 - Mon, Oct 13
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$371 Roundtrip, found 3 days ago
$371
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Fri, Oct 10 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Oct 13, priced at $371 found 3 days ago
JetBlue Airways
Tue, Apr 29 - Wed, May 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$450 Roundtrip, found 2 days ago
$450
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Apr 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 7, priced at $450 found 2 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 May, 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 $96, 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 $96 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$96

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 $146 per night from Apr 27 to Apr 28
$146
includes taxes & fees
Apr 27 - Apr 28
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! (1,003 reviews)
"This was my second time this year at your hotel. Your staff is amazing. They all making me feel comfortable at all times. From the front desk to the front door and restaurant staff. Thank you for another wonderful experience. See you soon!"

Reviewed on Apr 15, 2025

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
The price is $112 per night from Apr 27 to Apr 28
$112
includes taxes & fees
Apr 27 - Apr 28
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! (1,003 reviews)
"Room not super clean, lots of hair on the bathroom floor and shower"

Reviewed on Apr 14, 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
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 $222 per night from Apr 20 to Apr 21
$222
includes taxes & fees
Apr 20 - Apr 21
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)
"Nice breakfast. Quiet room."

Reviewed on Apr 17, 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 $162 per night from Apr 27 to Apr 28
$162
includes taxes & fees
Apr 27 - Apr 28
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 ...
8.2/10 Very Good! (1,002 reviews)
"Room was big enough. Very convenient area overall for food, commuting, and shopping."

Reviewed on Apr 16, 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 $69 per night from Apr 27 to Apr 28
$69
includes taxes & fees
Apr 27 - Apr 28
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! (1,008 reviews)
"Overall the hotel was neat and clean. The staff was pleasant."

Reviewed on Apr 15, 2025

Super 8 by Wyndham South Holland
Sophy Hyde Park
Sophy Hyde Park
4 out of 5
1411 East 53rd Street, Chicago, IL
The price is $296 per night from Apr 20 to Apr 21
$296
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4-star luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (939 reviews)
Perfection
"This is a comfortable, beautiful hotel in a great location."

Reviewed on Apr 14, 2025

Sophy Hyde Park
Wingate by Wyndham Tinley Park
Wingate by Wyndham Tinley Park
2.5 out of 5
18421 N Creek Drive, Tinley Park, IL
The price is $136 per night from May 11 to May 12
$136
includes taxes & fees
May 11 - May 12
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! (1,002 reviews)
"Everything was great from the staff cleanliness and"

Reviewed on Apr 16, 2025

Wingate by Wyndham Tinley 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 $95 per night from Apr 27 to Apr 28
$95
includes taxes & fees
Apr 27 - Apr 28
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 (1,002 reviews)
"I loved that there is a gas station so close by."

Reviewed on Apr 6, 2025

La Quinta Inn & Suites by Wyndham Chicago Tinley Park
See all 743 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.