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Highland Park

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Highland Park Flights as Low as $66

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

Frontier Airlines
Wed, Mar 11 - Wed, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$66 Roundtrip, found 1 day ago
$66
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Mar 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 11, priced at $66 found 1 day ago
Spirit Airlines
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $74 found 1 day ago
Frontier Airlines
Tue, May 5 - Sat, May 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 9, priced at $88 found 3 days ago
Frontier Airlines
Thu, Apr 16 - Sun, Apr 19
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$95 Roundtrip, found 15 hours ago
$95
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Austin-Bergstrom Intl. to O'Hare Intl., returning Sun, Apr 19, priced at $95 found 15 hours ago
Frontier Airlines
Wed, Mar 25 - Wed, Apr 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$106 Roundtrip, found 2 days ago
$106
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Apr 1, priced at $106 found 2 days ago
United
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 6 hours ago
$132
Roundtrip
found 6 hours ago
Select United flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $132 found 6 hours ago
Delta
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 6 hours ago
$132
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $132 found 6 hours ago
American Airlines
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 6 hours ago
$147
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $147 found 6 hours ago
Frontier Airlines
Thu, Feb 26 - Sat, Feb 28
AUS
Austin-Bergstrom Intl.
MDW
Midway Intl.
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Austin-Bergstrom Intl. to Midway Intl., returning Sat, Feb 28, priced at $196 found 1 day ago
Frontier Airlines
Thu, Apr 9 - Tue, Apr 14
LAX
Los Angeles Intl.
MDW
Midway Intl.
$214 Roundtrip, found 17 hours ago
$214
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Los Angeles Intl. to Midway Intl., returning Tue, Apr 14, priced at $214 found 17 hours ago
American Airlines
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Mar 17 from Los Angeles Intl. to Greater Rockford, returning Wed, Mar 25, priced at $242 found 3 days ago
Alaska Airlines
Tue, Mar 17 - Tue, Mar 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Mar 17 from Los Angeles Intl. to O'Hare Intl., returning Tue, Mar 24, priced at $265 found 1 day ago
American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$291 Roundtrip, found 5 days ago
$291
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $291 found 5 days ago
Arajet
Thu, Jul 16 - Mon, Aug 17
NLU
Felipe Ángeles Intl.
ORD
O'Hare Intl.
$311 Roundtrip, found 1 day ago
$311
Roundtrip
found 1 day ago
Select Arajet flight, departing Thu, Jul 16 from Felipe Ángeles Intl. to O'Hare Intl., returning Mon, Aug 17, priced at $311 found 1 day ago
Aeromexico
Wed, Jul 15 - Wed, Aug 19
MEX
Mexico City Intl.
ORD
O'Hare Intl.
$332 Roundtrip, found 1 day ago
$332
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Wed, Jul 15 from Mexico City Intl. to O'Hare Intl., returning Wed, Aug 19, priced at $332 found 1 day ago
Viva
Mon, Jul 13 - Thu, Aug 20
TLC
Toluca Intl.
ORD
O'Hare Intl.
$524 Roundtrip, found 1 day ago
$524
Roundtrip
found 1 day ago
Select Viva flight, departing Mon, Jul 13 from Toluca Intl. to O'Hare Intl., returning Thu, Aug 20, priced at $524 found 1 day 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 March, 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 $66, 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 $66 right now, why wait?

Highland Park Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$67

Last Minute Hotel Deals in Highland Park

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.2/10 Very Good! (2,202 reviews)
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on Feb 9, 2026

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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
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (2,736 reviews)
The friendliness of the staff.

Reviewed on Feb 9, 2026

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Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8/10 Very Good! (2,870 reviews)
Great place for the night

Reviewed on Feb 13, 2026

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Comfort Suites Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
8.6/10 Excellent! (1,222 reviews)
Clean room and staff was excellent

Reviewed on Feb 12, 2026

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Marriott Chicago O'Hare
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 business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,372 reviews)
I enjoy staying at the Hyatt Regency O'Hare. It’s usually a quick trip and my stay is always enjoyable. The hotel feels upscale, clean and it’s convenient. Parking is also easy since they have an attached garage.

Reviewed on Feb 13, 2026

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Hyatt Regency O'Hare Chicago
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
1140 North Wells Street Chicago IL
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our ...
9/10 Wonderful! (426 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

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Level Chicago – Old Town
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this 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! (1,291 reviews)
Great hotel with great location. Would definitely stay here again.

Reviewed on Jan 30, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
1118 North State Street Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our ...
9.4/10 Exceptional! (1,169 reviews)
This was my first stay at a hotel with my dog and they had already placed a dog bed and food bowls in the room. We were greeted with a dog treat and everyone already knew her name and we were greeted by name everytime we went through the lobby.

Reviewed on Feb 9, 2026

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Viceroy Chicago
See all 2,743 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.