Search Cheap Flights to
Highland Park

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Highland Park Flights as Low as $88

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

Frontier Airlines
Tue, Sep 9 - Tue, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $88 found 1 day ago
Frontier Airlines
Mon, Aug 4 - Thu, Aug 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 4 days ago
$90
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Aug 4 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $90 found 4 days ago
Spirit Airlines
Wed, Jul 23 - Wed, Jul 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jul 23 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $100 found 2 days ago
Frontier Airlines
Tue, Aug 5 - Sat, Aug 9
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Aug 9, priced at $101 found 1 day ago
Frontier Airlines
Tue, Jul 29 - Thu, Aug 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jul 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $112 found 1 day ago
Frontier Airlines
Mon, Jul 21 - Sat, Jul 26
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$121 Roundtrip, found 6 days ago
$121
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Jul 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jul 26, priced at $121 found 6 days ago
Spirit Airlines
Wed, Jul 30 - Thu, Aug 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$122 Roundtrip, found 13 hours ago
$122
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Wed, Jul 30 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $122 found 13 hours ago
Frontier Airlines
Mon, Jul 21 - Tue, Jul 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$123 Roundtrip, found 3 days ago
$123
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jul 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $123 found 3 days ago
Spirit Airlines
Tue, Nov 4 - Tue, Nov 11
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Nov 4 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Nov 11, priced at $132 found 1 day ago
United
Tue, Nov 4 - Tue, Nov 11
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select United flight, departing Tue, Nov 4 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Nov 11, priced at $147 found 1 day ago
American Airlines
Tue, Sep 9 - Tue, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $152 found 1 day ago
Delta
Tue, Sep 9 - Tue, Sep 16
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$167 Roundtrip, found 2 hours ago
$167
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Sep 9 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Sep 16, priced at $167 found 2 hours ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day 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 1 day ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 found 1 day ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 1 day ago
Frontier Airlines
Tue, Jul 15 - Fri, Jul 18
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$237 Roundtrip, found 9 hours ago
$237
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Jul 15 from Newark Liberty Intl. Airport to Midway Intl., returning Fri, Jul 18, priced at $237 found 9 hours ago

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 September, 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 $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 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 $88 right now, why wait?

Highland Park Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$71

Last Minute Hotel Deals in Highland Park

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! (1,695 reviews)
"Super helpful staff and very accommodating!"

Reviewed on Jun 30, 2025

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Hyatt Regency O'Hare Chicago
Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
3.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7.8/10 Good! (1,277 reviews)
"Quite"

Reviewed on Jun 30, 2025

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Super 8 by Wyndham Chicago O'Hare Airport
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! (2,081 reviews)
"It was very conveniently located outside of terminal 2."

Reviewed on Jul 1, 2025

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Hilton 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
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! (2,264 reviews)
"Perfect location if youre going to the Rosemont theater, as its right across the street. The hotel isnt well air conditioned, but the rooms are clean and you can control your temperature in there, which is important. The only thing i would say would be maybe extend restaurant hours on event nights...otherwise ..."

Reviewed on Jul 1, 2025

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Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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! (1,007 reviews)
"Great location and decent rooms. I had a strange experience in that two days in to my four day stay management ( dressed in plain, casual clothes of shorts and tshirt) came to my door and told me I wasn’t supposed to be in my room; that my room was supposed to be vacant. I would have questioned wether ..."

Reviewed on Jul 2, 2025

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The Chicago Hotel Collection Ambassador Gold Coast
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! (1,137 reviews)
"Beautiful location and room was beautiful!"

Reviewed on Jul 1, 2025

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Thompson Chicago, by Hyatt
Marriott Chicago O'Hare
Marriott Chicago O'Hare
3.5 out of 5
8535 West Higgins Road, Chicago, IL
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! (1,077 reviews)
"Loved the property, amenities, staff and overall experience. Its so convenient by the CTA, and expressway. Having the ability to have breakfast on location is great as well. The only reason I did not give 5 starts was due to the hallways being VERY warm (well over 80 at all times) and when the temp ..."

Reviewed on Jun 30, 2025

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Marriott Chicago O'Hare
Hyatt Place Chicago/O'Hare Airport
Hyatt Place Chicago/O'Hare Airport
3 out of 5
6810 Mannheim Rd, Rosemont, IL
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! (2,959 reviews)
"Pretty decent"

Reviewed on Jul 1, 2025

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Hyatt Place Chicago/O'Hare Airport
See all 2,493 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.