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Highland

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Highland Flights as Low as $88

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

Frontier Airlines
Wed, May 7 - Wed, May 14
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$88 Roundtrip, found 12 hours ago
$88
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, May 14, priced at $88 found 12 hours ago
Frontier Airlines
Wed, May 7 - Wed, May 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 3 hours ago
$88
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 14, priced at $88 found 3 hours ago
Frontier Airlines
Sat, May 10 - Mon, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$95 Roundtrip, found 3 hours ago
$95
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, May 10 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, May 12, priced at $95 found 3 hours ago
Frontier Airlines
Tue, May 6 - Thu, May 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 3 hours ago
$96
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, May 15, priced at $96 found 3 hours ago
American Airlines
Tue, May 6 - Thu, May 8
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, May 6 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, May 8, priced at $97 found 3 days ago
Delta
Wed, May 28 - Thu, May 29
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, May 28 from Minneapolis - St. Paul Intl. to Midway Intl., returning Thu, May 29, priced at $97 found 3 days ago
United
Thu, May 8 - Mon, May 12
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select United flight, departing Thu, May 8 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, May 12, priced at $97 found 3 days ago
Delta
Thu, May 8 - Mon, May 12
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, May 8 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, May 12, priced at $97 found 3 days ago
Frontier Airlines
Wed, May 7 - Sat, May 10
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$98 Roundtrip, found 12 hours ago
$98
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, May 10, priced at $98 found 12 hours ago
Frontier Airlines
Tue, May 6 - Sat, May 10
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$99 Roundtrip, found 12 hours ago
$99
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, May 6 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, May 10, priced at $99 found 12 hours ago
Spirit Airlines
Sun, Apr 13 - Sat, Apr 19
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$99 Roundtrip, found 5 days ago
$99
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sun, Apr 13 from George Bush Intercontinental to O'Hare Intl., returning Sat, Apr 19, priced at $99 found 5 days ago
Sun Country Airlines
Thu, May 8 - Mon, May 12
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Thu, May 8 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, May 12, priced at $107 found 3 days ago
Frontier Airlines
Thu, Apr 10 - Tue, Apr 15
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 4 days ago
$148
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Apr 10 from Charlotte-Douglas Intl. to O'Hare Intl., returning Tue, Apr 15, priced at $148 found 4 days ago
Frontier Airlines
Fri, Apr 4 - Mon, Apr 7
IAH
George Bush Intercontinental
MDW
Midway Intl.
$189 Roundtrip, found 4 hours ago
$189
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Apr 4 from George Bush Intercontinental to Midway Intl., returning Mon, Apr 7, priced at $189 found 4 hours ago
Delta
Thu, May 15 - Thu, May 22
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, May 15 from Charlotte-Douglas Intl. to Midway Intl., returning Thu, May 22, priced at $197 found 4 days ago
JetBlue Airways
Sat, May 3 - Sat, May 3
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$254 Roundtrip, found 6 days ago
$254
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, May 3 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 3, priced at $254 found 6 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 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 $88, 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 $88 right now, why wait?

Highland Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$88

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 $137 per night from Apr 7 to Apr 8
$137
includes taxes & fees
Apr 7 - Apr 8
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! (1,006 reviews)
"Very nice hotel. The staff were friendly especially Mrs. Barb, her hospitality was amazing. I would definitely stay at this hotel the next time I'm in town"

Reviewed on Mar 27, 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 $126 per night from Apr 20 to Apr 21
$126
includes taxes & fees
Apr 20 - Apr 21
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! (1,006 reviews)
"Bathroom next to event room was out of order…bartender for open bar could’ve been nicer"

Reviewed on Mar 29, 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 $86 per night from Apr 2 to Apr 3
$86
includes taxes & fees
Apr 2 - Apr 3
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! (1,003 reviews)
"Great"

Reviewed on Mar 22, 2025

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 $177 per night from Apr 7 to Apr 8
$177
includes taxes & fees
Apr 7 - Apr 8
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! (1,008 reviews)
"It was a good option for the night before visiting the nearby hospital. Lots of close dining options"

Reviewed on Mar 31, 2025

Hyatt Place Chicago-South/University Medical Center
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 6 to Apr 7
$112
includes taxes & fees
Apr 6 - Apr 7
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! (1,006 reviews)
"Fast and easy check in. Room is very nice, clean, and has a very comfy bed!"

Reviewed on Mar 29, 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Hyatt Place Munster
Hyatt Place Munster
3 out of 5
9420 Calumet Ave, Munster, IN
The price is $137 per night from Apr 7 to Apr 8
$137
includes taxes & fees
Apr 7 - Apr 8
Stay at this 3-star business-friendly hotel in Munster. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (316 reviews)
"Style"

Reviewed on Mar 30, 2025

Hyatt Place Munster
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 $113 per night from Apr 20 to Apr 21
$113
includes taxes & fees
Apr 20 - Apr 21
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! (1,004 reviews)
"We had a great stay at Wyndham. The entire facility was very clean, and updated. It was pretty quiet, just typical noise from the parking lot but even that was minimal The room was perfect. Bed was very comfortable, lots of space, shower had good pressure. The breakfast was nothing to write home ..."

Reviewed on Mar 26, 2025

Wingate by Wyndham Tinley Park
Sophy Hyde Park
Sophy Hyde Park
4 out of 5
1411 East 53rd Street, Chicago, IL
The price is $296 per night from Apr 6 to Apr 7
$296
includes taxes & fees
Apr 6 - Apr 7
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! (932 reviews)
"Great staff and very clean. Loved the decor in the room"

Reviewed on Mar 21, 2025

Sophy Hyde 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.