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Highwood

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Highwood Flights as Low as $72

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

Spirit Airlines
Mon, May 19 - Thu, May 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 3 hours ago
$72
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Mon, May 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, May 22, priced at $72 found 3 hours ago
Spirit Airlines
Sun, May 18 - Thu, May 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 3 hours ago
$73
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, May 22, priced at $73 found 3 hours ago
Frontier Airlines
Tue, May 6 - Sun, May 11
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$82 Roundtrip, found 6 days ago
$82
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, May 6 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sun, May 11, priced at $82 found 6 days ago
Spirit Airlines
Mon, May 19 - Fri, May 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 3 hours ago
$84
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Mon, May 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Fri, May 23, priced at $84 found 3 hours ago
Spirit Airlines
Sun, May 18 - Fri, May 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$86 Roundtrip, found 3 hours ago
$86
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Fri, May 23, priced at $86 found 3 hours ago
Frontier Airlines
Wed, May 7 - Mon, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, May 19, priced at $88 found 6 days ago
Frontier Airlines
Fri, May 9 - Sat, May 17
MCO
Orlando Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 9 from Orlando Intl. to O'Hare Intl., returning Sat, May 17, priced at $98 found 6 days ago
Frontier Airlines
Thu, Jul 24 - Sun, Jul 27
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jul 24 from Austin-Bergstrom Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $129 found 2 days ago
Frontier Airlines
Fri, Jul 18 - Mon, Jul 21
MCO
Orlando Intl.
MDW
Midway Intl.
$131 Roundtrip, found 3 days ago
$131
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jul 18 from Orlando Intl. to Midway Intl., returning Mon, Jul 21, priced at $131 found 3 days ago
Delta
Tue, Jun 10 - Tue, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 10 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 10, priced at $157 found 3 days ago
American Airlines
Tue, Jun 10 - Tue, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 10 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 10, priced at $157 found 3 days ago
United
Sat, May 31 - Tue, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select United flight, departing Sat, May 31 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 10, priced at $159 found 3 days ago
Spirit Airlines
Sun, May 25 - Tue, May 27
SAT
San Antonio Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 3 hours ago
$195
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sun, May 25 from San Antonio Intl. to O'Hare Intl., returning Tue, May 27, priced at $195 found 3 hours ago
Frontier Airlines
Sat, May 24 - Sun, Jun 1
SAT
San Antonio Intl.
MDW
Midway Intl.
$202 Roundtrip, found 19 hours ago
$202
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from San Antonio Intl. to Midway Intl., returning Sun, Jun 1, priced at $202 found 19 hours ago
Frontier Airlines
Sat, May 24 - Sat, May 31
AUS
Austin-Bergstrom Intl.
MDW
Midway Intl.
$212 Roundtrip, found 5 days ago
$212
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 24 from Austin-Bergstrom Intl. to Midway Intl., returning Sat, May 31, priced at $212 found 5 days ago
JetBlue Airways
Wed, Jun 11 - Sat, Jun 14
MCO
Orlando Intl.
ORD
O'Hare Intl.
$220 Roundtrip, found 3 days ago
$220
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Jun 11 from Orlando Intl. to O'Hare Intl., returning Sat, Jun 14, priced at $220 found 3 days ago

Cheap Flights to Highwood

Fall in love at first flight with your vacation to Highwood 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 Highwood on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Highwood, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Highwood

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Highwood 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 ORD airport.

What is the cheapest month to fly to Highwood?

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 Highwood are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Highwood?

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 Highwood.

What airport is best to fly into Highwood?

When you’re planning your trip to Highwood, convenience is the name of the game. Luckily, Highwood Chicago Executive Airport is nearby so you can deplane and get going on checking off everything on your Highwood must-do list.

How much are flights to Highwood?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Highwood on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $72, 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 Highwood?

The trick to saving a stack of cash on your flight to Highwood? 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 $72 right now, why wait?

Highwood Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$72

Last Minute Hotel Deals in Highwood

Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is $173 per night from May 18 to May 19
$173
includes taxes & fees
May 18 - May 19
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,527 reviews)
"Great classic Hyatt hotel!"

Reviewed on Apr 29, 2025

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare
Marriott Chicago O'Hare
3.5 out of 5
8535 West Higgins Road, Chicago, IL
The price is $198 per night from May 23 to May 24
$198
includes taxes & fees
May 23 - May 24
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
8.4/10 Very Good! (1,019 reviews)
"Nice property. Clean."

Reviewed on Apr 25, 2025

Marriott Chicago O'Hare
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
The price is $238 per night from May 24 to May 25
$238
includes taxes & fees
May 24 - May 25
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8/10 Very Good! (2,033 reviews)
"VERY CONVIENT"

Reviewed on Apr 28, 2025

Hilton Chicago O'Hare Airport
La Quinta by Wyndham Chicago O'Hare Airport
La Quinta by Wyndham Chicago O'Hare Airport
2.5 out of 5
6860 Mannheim Rd, Rosemont, IL
The price is $115 per night from May 12 to May 13
$115
includes taxes & fees
May 12 - May 13
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,376 reviews)
"The hotel was clean and quiet. I had a good night and slept like a baby. I’ve enjoyed the free breakfast buffet as well. Would definitely recommend them"

Reviewed on Apr 28, 2025

La Quinta by Wyndham Chicago O'Hare Airport
Hyatt Place Chicago/O'Hare Airport
Hyatt Place Chicago/O'Hare Airport
3 out of 5
6810 Mannheim Rd, Rosemont, IL
The price is $131 per night from May 19 to May 20
$131
includes taxes & fees
May 19 - May 20
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.2/10 Very Good! (2,902 reviews)
"This is a nice comforting place to do a get a way. We had a wonderful time."

Reviewed on Apr 27, 2025

Hyatt Place Chicago/O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
3.5 out of 5
5440 N River Rd, Rosemont, IL
The price is $154 per night from May 10 to May 11
$154
includes taxes & fees
May 10 - May 11
Stay at this 3.5-star business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.6/10 Excellent! (2,082 reviews)
"Very nice, staff was very helpful."

Reviewed on Apr 28, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
SpringHill Suites Chicago O'Hare by Marriott
SpringHill Suites Chicago O'Hare by Marriott
3 out of 5
8101 West Higgins Road, Chicago, IL
The price is $123 per night from May 25 to May 26
$123
includes taxes & fees
May 25 - May 26
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,170 reviews)
"Todo bien, solo que yo pedí un tipo de habitación a Expedia y me dieron otra."

Reviewed on Apr 28, 2025

SpringHill Suites Chicago O'Hare by Marriott
Holiday Inn Chicago O'Hare – Rosemont by IHG
Holiday Inn Chicago O'Hare – Rosemont by IHG
3 out of 5
6600 Mannheim Road, building 2, Rosemont, IL
The price is $119 per night from May 4 to May 5
$119
includes taxes & fees
May 4 - May 5
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
8.8/10 Excellent! (1,977 reviews)
"The night staff and morning staff were excellent and accommodating"

Reviewed on Apr 28, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG
See all 1,219 properties in Highwood
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.