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Highland

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Highland Flights as Low as $75

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

Spirit Airlines
Tue, Jul 22 - Wed, Jul 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$75 Roundtrip, found 13 hours ago
$75
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Tue, Jul 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $75 found 13 hours ago
Frontier Airlines
Tue, Jul 22 - Wed, Jul 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$92 Roundtrip, found 13 hours ago
$92
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Jul 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $92 found 13 hours ago
Frontier Airlines
Tue, Jul 15 - Wed, Jul 23
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$92 Roundtrip, found 5 days ago
$92
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jul 15 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jul 23, priced at $92 found 5 days ago
Spirit Airlines
Wed, Jul 30 - Wed, Aug 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 13 hours ago
$100
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Wed, Jul 30 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $100 found 13 hours ago
Spirit Airlines
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 4 hours ago
$130
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $130 found 4 hours ago
United
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 3 hours ago
$132
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $132 found 3 hours ago
Delta
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 3 hours ago
$132
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $132 found 3 hours ago
American Airlines
Sat, Aug 16 - Sat, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 13 hours ago
$132
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $132 found 13 hours ago
Frontier Airlines
Tue, Aug 12 - Wed, Aug 13
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$151 Roundtrip, found 13 hours ago
$151
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Aug 12 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Aug 13, priced at $151 found 13 hours ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 13 hours ago
$189
Roundtrip
found 13 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 $189 found 13 hours ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 13 hours ago
$191
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 found 13 hours ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 13 hours ago
$197
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 13 hours ago
Alaska Airlines
Tue, Oct 14 - Tue, Oct 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 13 hours ago
$216
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Tue, Oct 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $216 found 13 hours ago
Delta
Mon, Aug 11 - Tue, Aug 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 13 hours ago
$255
Roundtrip
found 13 hours ago
Select Delta flight, departing Mon, Aug 11 from Los Angeles Intl. to Midway Intl., returning Tue, Aug 12, priced at $255 found 13 hours ago
JetBlue Airways
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$273 Roundtrip, found 13 hours ago
$273
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $273 found 13 hours 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 13 hours ago
$325
Roundtrip
found 13 hours 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 13 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 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 $75, 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 $75 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$75

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! (1,004 reviews)
"We enjoyed a comfortable stay in a location near family and friends. We'll return."

Reviewed on Jun 30, 2025

Get rates
Hilton Chicago/Oak Lawn
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.
5.4/10 (30 reviews)
"Dirty"

Reviewed on Jun 23, 2025

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Motel 6 - Chicago, IL
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! (1,008 reviews)
"Staff were great. However, housekeeping did not clean our room during our 4 nights stay."

Reviewed on Jul 3, 2025

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Ameristar Casino Hotel East Chicago
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! (1,001 reviews)
"My very first time staying at any IHG property! This property was very clean felt safe and the staff were great. I am lifetime gold with a competitor who had no availability in the area. I would not hesitate staying here again."

Reviewed on Jul 1, 2025

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EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
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 (1,001 reviews)
"Remote matched TV. Plenty of things eels"

Reviewed on Jun 30, 2025

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Red Roof Inn Chicago - Lansing
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! (1,005 reviews)
"Check in was very easy and staff was so nice. I will definitely visit this location again."

Reviewed on Jul 4, 2025

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DoubleTree by Hilton Chicago - Alsip
Fairfield Inn and Suites By Marriott Merrillville
Fairfield Inn and Suites By Marriott Merrillville
2.5 out of 5
8275 Georgia St, Merrillville, IN
Book a stay at this business-friendly hotel in Merrillville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,001 reviews)
"The hotel and room was immaculate. The staff was cordial and the hot breakfast was outstanding. I don't have any complaints whatsoever. Bottom line is I would definitely stay here again."

Reviewed on Jun 26, 2025

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Fairfield Inn and Suites By Marriott Merrillville
Rodeway Inn
Rodeway Inn
2.5 out of 5
6200 Melton Rd, US Hwy 20, Portage, IN
Book a stay at this family-friendly hotel in Portage. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Founders' Square Park and East Branch ...
7/10 Good! (699 reviews)
"The hotel itself was nice. Our key card stopped working every other time we used it. Location was nice."

Reviewed on Jun 27, 2025

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Rodeway Inn
See all 800 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.