Search Cheap Flights to
Highland Park

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Highland Park Flights as Low as $43

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

Frontier Airlines
Wed, Mar 12 - Wed, Mar 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$43 Roundtrip, found 3 days ago
$43
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Mar 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Mar 12, priced at $43 found 3 days ago
Frontier Airlines
Tue, Mar 25 - Tue, Apr 1
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$48 Roundtrip, found 6 days ago
$48
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Mar 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, Apr 1, priced at $48 found 6 days ago
Frontier Airlines
Wed, Mar 26 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 2 days ago
$48
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $48 found 2 days ago
Spirit Airlines
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 2 days ago
$48
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $48 found 2 days ago
Frontier Airlines
Wed, Mar 5 - Wed, Mar 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$54 Roundtrip, found 2 days ago
$54
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 12, priced at $54 found 2 days ago
Spirit Airlines
Wed, Mar 19 - Wed, Mar 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$55 Roundtrip, found 15 hours ago
$55
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Wed, Mar 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 19, priced at $55 found 15 hours ago
Spirit Airlines
Tue, Mar 25 - Tue, Apr 1
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$57 Roundtrip, found 6 days ago
$57
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Mar 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, Apr 1, priced at $57 found 6 days ago
Frontier Airlines
Wed, Mar 26 - Mon, Apr 7
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 2 days ago
$58
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Apr 7, priced at $58 found 2 days ago
Spirit Airlines
Tue, Apr 1 - Wed, Apr 2
MSY
Louis Armstrong New Orleans Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Apr 1 from Louis Armstrong New Orleans Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $78 found 2 days ago
Delta
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $134 found 2 days ago
Frontier Airlines
Thu, Apr 10 - Tue, Apr 15
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$135 Roundtrip, found 13 hours ago
$135
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Apr 10 from Louis Armstrong New Orleans Intl. to Midway Intl., returning Tue, Apr 15, priced at $135 found 13 hours ago
United
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select United flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $139 found 2 days ago
American Airlines
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $159 found 2 days ago
Frontier Airlines
Fri, Feb 21 - Wed, Feb 26
IAH
George Bush Intercontinental
MDW
Midway Intl.
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 21 from George Bush Intercontinental to Midway Intl., returning Wed, Feb 26, priced at $180 found 1 day ago
JetBlue Airways
Sat, Mar 8 - Tue, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Mar 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 11, priced at $309 found 3 days ago
Delta
Fri, Jun 13 - Tue, Jun 17
CMH
John Glenn Columbus Intl.
MDW
Midway Intl.
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Jun 13 from John Glenn Columbus Intl. to Midway Intl., returning Tue, Jun 17, priced at $317 found 2 days 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 $43, 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 $43 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

Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is $132 per night from Feb 22 to Feb 23
$132
includes taxes & fees
Feb 22 - Feb 23
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! (1,302 reviews)
"The room was beautiful"

Reviewed on Feb 18, 2025

Hyatt Regency O'Hare Chicago
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
The price is $136 per night from Mar 10 to Mar 11
$136
includes taxes & fees
Mar 10 - Mar 11
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! (1,080 reviews)
"Such a nice, clean, and classy hotel. The downstairs is breakfast is amazing! The beds are super comfortable, that was the hardest part of saying goodbye haha"

Reviewed on Feb 18, 2025

Thompson Chicago, by Hyatt
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 $101 per night from Feb 23 to Feb 24
$101
includes taxes & fees
Feb 23 - Feb 24
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! (1,737 reviews)
"Perfect for a spending a night before getting on an early morning flight at OHare. Free Shuttle free parking. Low stress. Clean rooms. Nice facility."

Reviewed on Feb 19, 2025

Hampton Inn Chicago-O'Hare International Airport
Hyatt Regency Schaumburg Chicago
Hyatt Regency Schaumburg Chicago
4 out of 5
1800 East Golf Rd, Schaumburg, IL
The price is $101 per night from Feb 21 to Feb 22
$101
includes taxes & fees
Feb 21 - Feb 22
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 ...
8.2/10 Very Good! (1,001 reviews)
"I loved it"

Reviewed on Feb 18, 2025

Hyatt Regency Schaumburg Chicago
Viceroy Chicago
Viceroy Chicago
4.5 out of 5
1118 North State Street, Chicago, IL
The price is $271 per night from Feb 24 to Feb 25
$271
includes taxes & fees
Feb 24 - Feb 25
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,004 reviews)
"The hotel was absolutely beautiful, great customer service, and the restaurants Somerset/Pandan were delicious. My fiancé and I went for our anniversary and cannot wait to go back!"

Reviewed on Feb 18, 2025

Viceroy Chicago
Claridge House
Claridge House
4 out of 5
1244 N Dearborn Parkway, Chicago, IL
The price is $129 per night from Feb 23 to Feb 24
$129
includes taxes & fees
Feb 23 - Feb 24
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! (1,224 reviews)
"Very beautiful building in a wonderful neighborhood."

Reviewed on Feb 16, 2025

Claridge House
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 $112 per night from Feb 23 to Feb 24
$112
includes taxes & fees
Feb 23 - Feb 24
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! (1,799 reviews)
"Convienent location right near the airport. Room was clean and staff were friendly and helpful."

Reviewed on Feb 18, 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 $129 per night from Feb 23 to Feb 24
$129
includes taxes & fees
Feb 23 - Feb 24
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! (1,987 reviews)
"Excellent location, I little bit outdated but other than that, great value."

Reviewed on Feb 16, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr, and IHG Hotel
See all 2,265 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.