Search Cheap Flights to
Highland Park

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Highland Park Flights as Low as $90

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

Spirit Airlines
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $90 just found
American Airlines
Tue, Sep 9 - Tue, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$143 Roundtrip, just found
$143
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $143 just found
United
Tue, Sep 9 - Tue, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$143 Roundtrip, just found
$143
Roundtrip
just found
Select United flight, departing Tue, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $143 just found
Frontier Airlines
Sat, Sep 20 - Sun, Sep 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 5 days ago
$148
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Sep 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $148 found 5 days ago
Spirit Airlines
Mon, Jul 7 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, just found
$150
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Jul 7 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $150 just found
Frontier Airlines
Sat, Aug 2 - Wed, Aug 6
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$152 Roundtrip, found 23 hours ago
$152
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Aug 2 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Aug 6, priced at $152 found 23 hours ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, just found
$191
Roundtrip
just found
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 just found
Delta
Tue, Sep 9 - Tue, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$191 Roundtrip, just found
$191
Roundtrip
just found
Select Delta flight, departing Tue, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $191 just found
Delta
Sat, Aug 2 - Sat, Aug 9
DAL
Love Field
MDW
Midway Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 2 from Love Field to Midway Intl., returning Sat, Aug 9, priced at $200 found 1 day ago
Contour Airlines
Sun, Jul 20 - Wed, Jul 23
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$204 Roundtrip, just found
$204
Roundtrip
just found
Select Contour Airlines flight, departing Sun, Jul 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $204 just found
Alaska Airlines
Tue, Oct 14 - Tue, Oct 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, just found
$216
Roundtrip
just found
Select Alaska Airlines flight, departing Tue, Oct 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $216 just found
United
Fri, Oct 17 - Mon, Oct 27
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$221 Roundtrip, just found
$221
Roundtrip
just found
Select United flight, departing Fri, Oct 17 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Mon, Oct 27, priced at $221 just found
Delta
Mon, Jul 14 - Tue, Jul 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Delta flight, departing Mon, Jul 14 from Los Angeles Intl. to Midway Intl., returning Tue, Jul 15, priced at $257 just found
Frontier Airlines
Sun, Jun 15 - Mon, Jun 16
ONT
Los Angeles - Ontario Intl.
MDW
Midway Intl.
$261 Roundtrip, found 10 hours ago
$261
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sun, Jun 15 from Los Angeles - Ontario Intl. to Midway Intl., returning Mon, Jun 16, priced at $261 found 10 hours ago
Sun Country Airlines
Mon, Jul 7 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$338 Roundtrip, just found
$338
Roundtrip
just found
Select Sun Country Airlines flight, departing Mon, Jul 7 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $338 just found
Hawaiian Airlines
Wed, Jul 9 - Thu, Jul 10
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$446 Roundtrip, just found
$446
Roundtrip
just found
Select Hawaiian Airlines flight, departing Wed, Jul 9 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Thu, Jul 10, priced at $446 just found

Cheap Flights to Highland Park

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

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

Frequently Asked Questions About flights to Highland Park

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

What is the cheapest month to fly to Highland Park?

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 Park are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Highland Park?

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 Park.

What airport is best to fly into Highland Park?

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

How much are flights to Highland Park?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Highland Park on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $90, 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 Park?

The trick to saving a stack of cash on your flight to Highland Park? 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 $90 right now, why wait?

Highland Park Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$96

Last Minute Hotel Deals in Highland Park

The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold Coast
4 out of 5
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,003 reviews)
"Loved it here ! We will stay here every time we visit Chicago!"

Reviewed on Jun 4, 2025

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The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
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! (1,601 reviews)
"Good hotel"

Reviewed on Jun 3, 2025

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Hyatt Regency O'Hare Chicago
Grand Royal Hotel O'Hare - Chicago
Grand Royal Hotel O'Hare - Chicago
3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
5/10 (47 reviews)
"This property had a restaurant attached which was very convenient. The staff was friendly and helpful during my stay."

Reviewed on Jun 1, 2025

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Grand Royal Hotel O'Hare - Chicago
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
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! (2,174 reviews)
"Excellent service and close to Airport"

Reviewed on Jun 3, 2025

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Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Hyatt Regency Schaumburg Chicago
Hyatt Regency Schaumburg Chicago
4 out of 5
1800 East Golf Rd, Schaumburg, IL
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,108 reviews)
"NA"

Reviewed on May 29, 2025

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Hyatt Regency Schaumburg Chicago
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
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! (2,066 reviews)
"Excelkent"

Reviewed on Jun 4, 2025

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Hilton Chicago O'Hare Airport
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the bar and the helpful staff in our reviews. ...
9/10 Wonderful! (1,125 reviews)
"Exellent location, friendly staff. Only one elevator was in service at the time of my stay in April 2025."

Reviewed on Jun 3, 2025

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Thompson Chicago, by Hyatt
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
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! (2,049 reviews)
"Good place to stay close to O’Hare and friendly staff."

Reviewed on Jun 4, 2025

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Holiday Inn Chicago O'Hare – Rosemont by IHG
See all 2,477 properties in Highland Park
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.