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Highland

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Highland Flights as Low as $84

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

Frontier Airlines
Sun, May 4 - Tue, May 6
MCO
Orlando Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, May 4 from Orlando Intl. to O'Hare Intl., returning Tue, May 6, priced at $84 found 2 days ago
Spirit Airlines
Thu, Mar 6 - Mon, Mar 10
MCO
Orlando Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Mar 6 from Orlando Intl. to O'Hare Intl., returning Mon, Mar 10, priced at $84 found 2 days ago
Frontier Airlines
Wed, Mar 5 - Tue, Mar 11
MCO
Orlando Intl.
ORD
O'Hare Intl.
$85 Roundtrip, found 3 days ago
$85
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Orlando Intl. to O'Hare Intl., returning Tue, Mar 11, priced at $85 found 3 days ago
Frontier Airlines
Thu, Apr 17 - Sat, Apr 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 6 days ago
$87
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Apr 17 from Denver Intl. to O'Hare Intl., returning Sat, Apr 19, priced at $87 found 6 days ago
Frontier Airlines
Tue, Mar 25 - Wed, Mar 26
MCO
Orlando Intl.
ORD
O'Hare Intl.
$89 Roundtrip, found 4 days ago
$89
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Mar 25 from Orlando Intl. to O'Hare Intl., returning Wed, Mar 26, priced at $89 found 4 days ago
United
Thu, Apr 24 - Mon, Apr 28
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select United flight, departing Thu, Apr 24 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Apr 28, priced at $117 found 5 days ago
Delta
Tue, Mar 11 - Wed, Mar 12
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Mar 11 from Minneapolis - St. Paul Intl. to Midway Intl., returning Wed, Mar 12, priced at $117 found 6 days ago
United
Thu, Apr 24 - Mon, Apr 28
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select United flight, departing Thu, Apr 24 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Apr 28, priced at $117 found 5 days ago
Delta
Thu, Apr 3 - Tue, Apr 8
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 11 hours ago
$117
Roundtrip
found 11 hours ago
Select Delta flight, departing Thu, Apr 3 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Apr 8, priced at $117 found 11 hours ago
Sun Country Airlines
Thu, Apr 24 - Fri, Apr 25
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Apr 24 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Fri, Apr 25, priced at $127 found 1 day ago
American Airlines
Wed, Mar 19 - Fri, Mar 21
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 13 hours ago
$132
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Mar 19 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Fri, Mar 21, priced at $132 found 13 hours ago
Frontier Airlines
Thu, Mar 27 - Tue, Apr 1
MCO
Orlando Intl.
MDW
Midway Intl.
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Mar 27 from Orlando Intl. to Midway Intl., returning Tue, Apr 1, priced at $158 found 4 days ago
Spirit Airlines
Fri, Apr 25 - Mon, Apr 28
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 9 hours ago
$164
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Fri, Apr 25 from Raleigh - Durham Intl. to O'Hare Intl., returning Mon, Apr 28, priced at $164 found 9 hours ago
JetBlue Airways
Sat, May 3 - Tue, May 6
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, May 3 from Raleigh - Durham Intl. to O'Hare Intl., returning Tue, May 6, priced at $193 found 1 day ago
Frontier Airlines
Tue, Feb 25 - Tue, Mar 4
DEN
Denver Intl.
MDW
Midway Intl.
$230 Roundtrip, found 13 hours ago
$230
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Feb 25 from Denver Intl. to Midway Intl., returning Tue, Mar 4, priced at $230 found 13 hours ago
Frontier Airlines
Wed, Feb 26 - Sat, Mar 1
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$290 Roundtrip, found 15 hours ago
$290
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Wed, Feb 26 from Raleigh - Durham Intl. to Midway Intl., returning Sat, Mar 1, priced at $290 found 15 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 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 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 $84, 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 $84 right now, why wait?

Highland Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$48

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 Mar 2 to Mar 3
$128
includes taxes & fees
Mar 2 - Mar 3
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! (1,003 reviews)
"Nice"

Reviewed on Feb 17, 2025

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 Mar 2 to Mar 3
$124
includes taxes & fees
Mar 2 - Mar 3
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! (1,002 reviews)
Noisy Heater
"The heater made a terrible whining noise. It would wake me up in the middle of the night."

Reviewed on Feb 12, 2025

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 $159 per night from Feb 25 to Feb 26
$159
includes taxes & fees
Feb 25 - Feb 26
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! (1,007 reviews)
"I love the location, the hotel is surrounded by many food options"

Reviewed on Feb 21, 2025

Hyatt Place Chicago-South/University Medical Center
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 $124 per night from Mar 2 to Mar 3
$124
includes taxes & fees
Mar 2 - Mar 3
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! (1,005 reviews)
Excellent
"This place is awesome. The staff really made the stay enjoyable and was very helpful. We ended up extending our stay for 2 more days."

Reviewed on Feb 21, 2025

Wingate by Wyndham Tinley Park
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 $106 per night from Mar 2 to Mar 3
$106
includes taxes & fees
Mar 2 - Mar 3
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)
"Very clean"

Reviewed on Feb 17, 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr, an IHG Hotel
Comfort Inn Chicago Wind Creek Casino
Comfort Inn Chicago Wind Creek Casino
2.5 out of 5
16900 S Halsted St, Harvey, IL
The price is $106 per night from Feb 24 to Feb 25
$106
includes taxes & fees
Feb 24 - Feb 25
Stay at this aparthotel in Harvey. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Midwest Carvers Museum and South Holland Village ...
Comfort Inn Chicago Wind Creek Casino
Motel 6 Hammond, IN - Chicago Area
Motel 6 Hammond, IN - Chicago Area
2 out of 5
3840 179th St, Hammond, IN
The price is $62 per night from Feb 24 to Feb 25
$62
includes taxes & fees
Feb 24 - Feb 25
Stay at this motel in Hammond. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.2/10 (1,001 reviews)
5 stars
"All around good place and great staff"

Reviewed on Feb 10, 2025

Motel 6 Hammond, IN - Chicago Area
Red Roof Inn Chicago - Lansing
Red Roof Inn Chicago - Lansing
2 out of 5
2450 East 173rd Street, Lansing, IL
The price is $70 per night from Feb 24 to Feb 25
$70
includes taxes & fees
Feb 24 - Feb 25
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 ...
4.2/10 (1,002 reviews)
"Great place to stay short term"

Reviewed on Feb 15, 2025

Red Roof Inn Chicago - Lansing
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.