Search Cheap Flights to
Highland Park

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Highland Park Flights as Low as $60

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

Frontier Airlines
Tue, Sep 23 - Tue, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$60 Roundtrip, found 2 days ago
$60
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 23 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Sep 30, priced at $60 found 2 days ago
Spirit Airlines
Wed, Aug 13 - Sat, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Aug 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $72 found 1 day ago
Frontier Airlines
Mon, Sep 15 - Thu, Sep 18
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Sep 15 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Sep 18, priced at $97 found 3 days ago
United
Sat, Oct 18 - Sat, Oct 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 20 hours ago
$132
Roundtrip
found 20 hours ago
Select United flight, departing Sat, Oct 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $132 found 20 hours ago
Delta
Sat, Oct 18 - Sat, Oct 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 20 hours ago
$132
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Oct 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $132 found 20 hours ago
American Airlines
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $134 found 3 days ago
Spirit Airlines
Fri, Aug 15 - Tue, Aug 19
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$140 Roundtrip, found 15 hours ago
$140
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Fri, Aug 15 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Aug 19, priced at $140 found 15 hours ago
Delta
Wed, Sep 10 - Tue, Sep 16
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Sep 10 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Sep 16, priced at $169 found 3 days ago
Hawaiian Airlines
Sat, Aug 30 - Sun, Aug 31
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 10 hours ago
$179
Roundtrip
found 10 hours ago
Select Hawaiian Airlines flight, departing Sat, Aug 30 from Seattle - Tacoma Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $179 found 10 hours ago
Bargain Flight
Sat, Nov 8 - Sat, Nov 8
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Nov 8 from Seattle - Tacoma Intl. to O'Hare Intl., returning Sat, Nov 8, priced at $182 found 1 day ago
Frontier Airlines
Sat, Aug 30 - Sun, Aug 31
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$201 Roundtrip, found 3 days ago
$201
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Charlotte-Douglas Intl. to Midway Intl., returning Sun, Aug 31, priced at $201 found 3 days ago
Frontier Airlines
Thu, Aug 14 - Sat, Aug 16
SEA
Seattle - Tacoma Intl.
MDW
Midway Intl.
$263 Roundtrip, found 1 day ago
$263
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Seattle - Tacoma Intl. to Midway Intl., returning Sat, Aug 16, priced at $263 found 1 day ago
Frontier Airlines
Fri, Aug 22 - Mon, Aug 25
PAE
Seattle Paine Field Intl. Airport
ORD
O'Hare Intl.
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 22 from Seattle Paine Field Intl. Airport to O'Hare Intl., returning Mon, Aug 25, priced at $268 found 1 day ago
JetBlue Airways
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$273 Roundtrip, found 18 hours ago
$273
Roundtrip
found 18 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 18 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 3 days ago
$325
Roundtrip
found 3 days 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 3 days ago
Sun Country Airlines
Fri, Aug 8 - Mon, Aug 11
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$495 Roundtrip, found 1 day ago
$495
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Fri, Aug 8 from Seattle - Tacoma Intl. to O'Hare Intl., returning Mon, Aug 11, priced at $495 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 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 15 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 $60, 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 $60 right now, why wait?

Highland Park Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$60

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
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! (2,090 reviews)
"Great"

Reviewed on Jul 27, 2025

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Hilton Chicago O'Hare Airport
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! (1,809 reviews)
"It was my adult children who stayed at your hotel. My son loved it with all the planes flying in and out from the airport. They were there for a concert that my daughter went to."

Reviewed on Jul 28, 2025

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Hyatt Regency 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! (2,350 reviews)
"The staff was very helpful."

Reviewed on Jul 28, 2025

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Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
Stay at this 4-star spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful ...
8.8/10 Excellent! (1,286 reviews)
"Over all felt like this was a really great property. Will definitely consider staying here again the next time I’m traveling to Chicago."

Reviewed on Jul 28, 2025

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Claridge House
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! (1,108 reviews)
"Great place. Very comfortable. No complaints"

Reviewed on Jul 28, 2025

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Marriott Chicago O'Hare
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! (1,057 reviews)
"Super convenient and friendly staff!"

Reviewed on Jul 25, 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! (1,183 reviews)
"Loved the location you will never find anything better than this..."

Reviewed on Jul 21, 2025

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Thompson Chicago, by Hyatt
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! (3,051 reviews)
"I liked all the above. Did not like food options. Poor."

Reviewed on Jul 28, 2025

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Hyatt Place Chicago/O'Hare Airport
See all 2,566 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.