Search Cheap Flights to
Highland

Photo by Joe Farmer

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Highland Flights as Low as $63

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

Spirit Airlines
Tue, Aug 12 - Tue, Aug 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 12, priced at $63 found 1 day ago
Spirit Airlines
Sat, Aug 23 - Wed, Aug 27
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 21 hours ago
$72
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sat, Aug 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 27, priced at $72 found 21 hours ago
Frontier Airlines
Tue, Sep 23 - Tue, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$75 Roundtrip, found 13 hours ago
$75
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Sep 23 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Sep 30, priced at $75 found 13 hours ago
Frontier Airlines
Wed, Aug 13 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$75 Roundtrip, found 22 hours ago
$75
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Aug 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $75 found 22 hours ago
Frontier Airlines
Wed, Aug 20 - Wed, Aug 27
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Aug 27, priced at $83 found 1 day ago
Frontier Airlines
Thu, Oct 2 - Tue, Oct 7
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$90 Roundtrip, found 15 hours ago
$90
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, Oct 2 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Oct 7, priced at $90 found 15 hours ago
Frontier Airlines
Mon, Sep 15 - Thu, Sep 18
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Sep 15 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Sep 18, priced at $97 found 1 day ago
Delta
Sat, Oct 18 - Sat, Oct 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $132 found 1 day ago
United
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select United flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $134 found 1 day ago
American Airlines
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $134 found 1 day ago
Delta
Tue, Aug 26 - Tue, Aug 26
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 15 hours ago
$191
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Aug 26 from Love Field to O'Hare Intl., returning Tue, Aug 26, priced at $191 found 15 hours ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 6 hours ago
$193
Roundtrip
found 6 hours ago
Select Contour Airlines flight, departing Mon, Sep 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $193 found 6 hours ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 15 hours ago
Delta
Wed, Aug 27 - Wed, Sep 3
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$198 Roundtrip, found 6 days ago
$198
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 27 from Charlotte-Douglas Intl. to Midway Intl., returning Wed, Sep 3, priced at $198 found 6 days ago
JetBlue Airways
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$272 Roundtrip, found 2 days ago
$272
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $272 found 2 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Dec 23 - Tue, Dec 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Dec 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 30, priced at $325 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 August, 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 $63, 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 $63 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

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! (1,022 reviews)
"The staff was extremely helpful in everything that we needed!"

Reviewed on Jul 21, 2025

Get rates
Hilton Chicago/Oak Lawn
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
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! (1,023 reviews)
"Great"

Reviewed on Jul 24, 2025

Get rates
Ameristar Casino Hotel East Chicago
Quality Inn & Suites Orland Park - Chicago

Quality Inn & Suites Orland Park - Chicago

2.5 out of 5
8800 W 159th St, Orland Park, IL
Book a stay at this business-friendly hotel in Orland Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.2/10 Good! (1,011 reviews)
"Good place to stay"

Reviewed on Jul 23, 2025

Get rates
Quality Inn & Suites Orland Park - Chicago
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located nearby.
6/10 (46 reviews)
"I appreciate all the people that work at this motel 6! They are polite and always willing to help with reservations. I also have a service animal and it's been so peaceful to stay there."

Reviewed on Jul 17, 2025

Get rates
Motel 6 - Chicago, IL
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,015 reviews)
"Nestled in the woods it was a nice place to stay. The room was very clean and the staff were very friendly."

Reviewed on Jul 24, 2025

Get rates
Spring House Inn
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! (1,016 reviews)
Great room, super comfortable bed
"We came for a concert, and while we didn't spend much time at the hotel, the time we were there was excellent, very comfortable room, quality decor and toiletries, overall very nice."

Reviewed on Jul 23, 2025

Get rates
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
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! (1,026 reviews)
"The room was comfortable, clean and quiet. The only problem I had was the hot water pressure was low in the sink."

Reviewed on Jul 21, 2025

Get rates
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! (1,011 reviews)
"Clean comfortable room. Pleasant staff. Nothing fancy or upscale but met our traveling needs for a clean & comfortable room. Breakfast choices limited good coffee."

Reviewed on Jul 23, 2025

Get rates
Baymont by Wyndham Chicago/Alsip
See all 823 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.