Search Cheap Flights to
Highland Park

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Highland Park Flights as Low as $48

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

Frontier Airlines
Tue, Feb 25 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$48 Roundtrip, found 1 day ago
$48
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Mar 4, priced at $48 found 1 day ago
Frontier Airlines
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $63 found 1 day ago
Spirit Airlines
Tue, Mar 25 - Tue, Apr 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 2 days ago
$73
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Mar 25 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Apr 1, priced at $73 found 2 days ago
Frontier Airlines
Wed, Mar 26 - Wed, Apr 2
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Mar 26 from Raleigh - Durham Intl. to Midway Intl., returning Wed, Apr 2, priced at $119 found 3 days ago
Frontier Airlines
Tue, Apr 15 - Thu, Apr 24
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Apr 15 from Raleigh - Durham Intl. to O'Hare Intl., returning Thu, Apr 24, priced at $119 found 1 day ago
American Airlines
Tue, Mar 4 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Mar 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 4, priced at $132 found 2 days ago
Delta
Wed, Mar 12 - Wed, Mar 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Mar 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Mar 12, priced at $134 found 2 days ago
United
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select United flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $137 found 1 day ago
JetBlue Airways
Tue, Feb 18 - Wed, Feb 19
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 1 hour ago
$193
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Feb 18 from Raleigh - Durham Intl. to O'Hare Intl., returning Wed, Feb 19, priced at $193 found 1 hour ago
Air Canada
Sun, Feb 2 - Sun, Feb 9
AKL
Auckland Intl.
ORD
O'Hare Intl.
$930 Roundtrip, found 1 day ago
$930
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Feb 2 from Auckland Intl. to O'Hare Intl., returning Sun, Feb 9, priced at $930 found 1 day ago
Qantas Airways
Mon, Feb 3 - Tue, Feb 11
AKL
Auckland Intl.
ORD
O'Hare Intl.
$1,162 Roundtrip, found 1 day ago
$1,162
Roundtrip
found 1 day ago
Select Qantas Airways flight, departing Mon, Feb 3 from Auckland Intl. to O'Hare Intl., returning Tue, Feb 11, priced at $1,162 found 1 day ago
Cathay Pacific
Tue, Feb 4 - Tue, Feb 11
AKL
Auckland Intl.
ORD
O'Hare Intl.
$1,229 Roundtrip, found 1 day ago
$1,229
Roundtrip
found 1 day ago
Select Cathay Pacific flight, departing Tue, Feb 4 from Auckland Intl. to O'Hare Intl., returning Tue, Feb 11, priced at $1,229 found 1 day ago
EVA Airways
Sat, Jun 14 - Wed, Jun 25
AKL
Auckland Intl.
ORD
O'Hare Intl.
$1,345 Roundtrip, found 1 day ago
$1,345
Roundtrip
found 1 day ago
Select EVA Airways flight, departing Sat, Jun 14 from Auckland Intl. to O'Hare Intl., returning Wed, Jun 25, priced at $1,345 found 1 day ago
Air New Zealand
Tue, Feb 4 - Tue, Feb 11
AKL
Auckland Intl.
ORD
O'Hare Intl.
$1,364 Roundtrip, found 1 day ago
$1,364
Roundtrip
found 1 day ago
Select Air New Zealand flight, departing Tue, Feb 4 from Auckland Intl. to O'Hare Intl., returning Tue, Feb 11, priced at $1,364 found 1 day ago
Korean Air
Tue, Feb 4 - Tue, Feb 11
AKL
Auckland Intl.
ORD
O'Hare Intl.
$1,608 Roundtrip, found 1 day ago
$1,608
Roundtrip
found 1 day ago
Select Korean Air flight, departing Tue, Feb 4 from Auckland Intl. to O'Hare Intl., returning Tue, Feb 11, priced at $1,608 found 1 day ago
Delta
Mon, Apr 14 - Tue, Apr 15
AKL
Auckland Intl.
MDW
Midway Intl.
$1,915 Roundtrip, found 1 day ago
$1,915
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Apr 14 from Auckland Intl. to Midway Intl., returning Tue, Apr 15, priced at $1,915 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 February, 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 $48, 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 $48 right now, why wait?

Highland Park Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$48

Last Minute Hotel Deals in Highland Park

Claridge House
Claridge House
4 out of 5
1244 N Dearborn Parkway, Chicago, IL
The price is $129 per night from Jan 13 to Jan 14
$129
includes taxes & fees
Jan 13 - Jan 14
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 ...
8.6/10 Excellent! (1,217 reviews)
"LOVELY STAY FOR THE MARATHON. LOVE THE COLD WATER NEAR RECEPTION."

Reviewed on Jan 4, 2025

Claridge House
Hampton Inn Chicago-O'Hare International Airport
Hampton Inn Chicago-O'Hare International Airport
2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
The price is $113 per night from Jan 19 to Jan 20
$113
includes taxes & fees
Jan 19 - Jan 20
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,624 reviews)
"Very good option for the price"

Reviewed on Jan 9, 2025

Hampton Inn Chicago-O'Hare International Airport
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
The price is $133 per night from Jan 27 to Jan 28
$133
includes taxes & fees
Jan 27 - Jan 28
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! (1,049 reviews)
"Loved the hotel, but they should have told us in advance that one of the two elevators was out of service. That made the stay less enjoyable."

Reviewed on Jan 6, 2025

Thompson Chicago, by Hyatt
Chicago Getaway Hostel
Chicago Getaway Hostel
2 out of 5
616 W Arlington Pl, Chicago, IL
The price is $73 per night from Jan 12 to Jan 13
$73
includes taxes & fees
Jan 12 - Jan 13
Stay at this hostel in Chicago. Enjoy parking (surcharge), a 24-hour front desk, and a business center. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,002 reviews)
comfy
"decent. happy abt bed quality n extra pillows when requested"

Reviewed on Jan 7, 2025

Chicago Getaway Hostel
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
The price is $158 per night from Jan 17 to Jan 18
$158
includes taxes & fees
Jan 17 - Jan 18
Stay at this 4.5-star luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the ...
9.2/10 Wonderful! (1,681 reviews)
"Excellent property! Up to date and very comfortable bedrooms."

Reviewed on Jan 9, 2025

Loews Chicago O'Hare Hotel
Comfort Suites Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
3 out of 5
4200 North River Road, Schiller Park, IL
The price is $90 per night from Jan 12 to Jan 13
$90
includes taxes & fees
Jan 12 - Jan 13
Stay at this 3-star 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! (2,345 reviews)
"Convenient location and airport shuttle availability."

Reviewed on Jan 5, 2025

Comfort Suites Chicago O'Hare Airport
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
3 out of 5
6600 Mannheim Road, building 2, Rosemont, IL
The price is $122 per night from Jan 14 to Jan 15
$122
includes taxes & fees
Jan 14 - Jan 15
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! (1,694 reviews)
"Nice clean hotel. The swimming pool water was a little cold. But overall nice place to stay"

Reviewed on Jan 8, 2025

Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
Crowne Plaza Chicago Ohare Hotel & Conf Ctr, and IHG Hotel
Crowne Plaza Chicago Ohare Hotel & Conf Ctr, and IHG Hotel
3.5 out of 5
5440 N River Rd, Rosemont, IL
The price is $114 per night from Jan 13 to Jan 14
$114
includes taxes & fees
Jan 13 - Jan 14
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! (1,933 reviews)
"Friendly staff and nice room."

Reviewed on Jan 6, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr, and IHG Hotel
See all 2,137 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.