Search Cheap Flights to
Highland Park

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Highland Park Flights as Low as $115

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

Frontier Airlines
Wed, May 14 - Wed, May 21
IAH
George Bush Intercontinental
MDW
Midway Intl.
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 14 from George Bush Intercontinental to Midway Intl., returning Wed, May 21, priced at $115 just found
Spirit Airlines
Thu, May 15 - Tue, May 20
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$133 Roundtrip, just found
$133
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 15 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 20, priced at $133 just found
Spirit Airlines
Sun, May 25 - Tue, May 27
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$135 Roundtrip, just found
$135
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, May 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 27, priced at $135 just found
Spirit Airlines
Thu, May 15 - Tue, May 20
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$141 Roundtrip, just found
$141
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 15 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 20, priced at $141 just found
Frontier Airlines
Sun, May 25 - Tue, May 27
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$142 Roundtrip, just found
$142
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, May 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 27, priced at $142 just found
American Airlines
Sun, May 11 - Fri, May 16
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$146 Roundtrip, just found
$146
Roundtrip
just found
Select American Airlines flight, departing Sun, May 11 from George Bush Intercontinental to O'Hare Intl., returning Fri, May 16, priced at $146 just found
Frontier Airlines
Sun, May 11 - Fri, May 16
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$146 Roundtrip, just found
$146
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, May 11 from George Bush Intercontinental to O'Hare Intl., returning Fri, May 16, priced at $146 just found
Spirit Airlines
Thu, May 15 - Tue, May 20
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$148 Roundtrip, just found
$148
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 15 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 20, priced at $148 just found
Frontier Airlines
Sat, May 24 - Tue, May 27
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$149 Roundtrip, just found
$149
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 24 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 27, priced at $149 just found
Spirit Airlines
Thu, May 15 - Tue, May 20
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$150 Roundtrip, just found
$150
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 15 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 20, priced at $150 just found
American Airlines
Sun, May 25 - Tue, May 27
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$191 Roundtrip, just found
$191
Roundtrip
just found
Select American Airlines flight, departing Sun, May 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 27, priced at $191 just found
United
Sun, May 25 - Tue, May 27
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$191 Roundtrip, just found
$191
Roundtrip
just found
Select United flight, departing Sun, May 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 27, priced at $191 just found
United
Wed, Apr 30 - Wed, May 7
GRB
Austin Straubel Intl.
ORD
O'Hare Intl.
$203 Roundtrip, just found
$203
Roundtrip
just found
Select United flight, departing Wed, Apr 30 from Austin Straubel Intl. to O'Hare Intl., returning Wed, May 7, priced at $203 just found
Delta
Sat, Jun 21 - Sat, Jun 21
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$211 Roundtrip, just found
$211
Roundtrip
just found
Select Delta flight, departing Sat, Jun 21 from George Bush Intercontinental to O'Hare Intl., returning Sat, Jun 21, priced at $211 just found
United
Thu, May 8 - Fri, May 16
ANC
Ted Stevens Anchorage Intl.
ORD
O'Hare Intl.
$437 Roundtrip, just found
$437
Roundtrip
just found
Select United flight, departing Thu, May 8 from Ted Stevens Anchorage Intl. to O'Hare Intl., returning Fri, May 16, priced at $437 just found
Alaska Airlines
Wed, May 14 - Sat, May 17
ANC
Ted Stevens Anchorage Intl.
ORD
O'Hare Intl.
$483 Roundtrip, just found
$483
Roundtrip
just found
Select Alaska Airlines flight, departing Wed, May 14 from Ted Stevens Anchorage Intl. to O'Hare Intl., returning Sat, May 17, priced at $483 just found

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 May, 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 $115, 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 $115 right now, why wait?

Highland Park Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$109

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 Apr 19 to Apr 20
$132
includes taxes & fees
Apr 19 - Apr 20
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! (1,477 reviews)
"This hotel is great"

Reviewed on Apr 17, 2025

Hyatt Regency O'Hare Chicago
Hyatt Regency Schaumburg Chicago
Hyatt Regency Schaumburg Chicago
4 out of 5
1800 East Golf Rd, Schaumburg, IL
The price is $137 per night from Apr 18 to Apr 19
$137
includes taxes & fees
Apr 18 - Apr 19
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 ...
8.4/10 Very Good! (1,028 reviews)
"Everything was great except the worn out mattress"

Reviewed on Apr 14, 2025

Hyatt Regency Schaumburg Chicago
Ambassador Hotel Chicago
Ambassador Hotel Chicago
4 out of 5
1301 N State Pkwy, Chicago, IL
The price is $147 per night from Apr 20 to Apr 21
$147
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,005 reviews)
"Great experience"

Reviewed on Apr 8, 2025

Ambassador Hotel Chicago
Holiday Inn Chicago North-Evanston by IHG
Holiday Inn Chicago North-Evanston by IHG
3 out of 5
1501 Sherman Ave, Evanston, IL
The price is $119 per night from Apr 20 to Apr 21
$119
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,292 reviews)
"Would stay here again!"

Reviewed on Apr 15, 2025

Holiday Inn Chicago North-Evanston by IHG
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
The price is $245 per night from Apr 18 to Apr 19
$245
includes taxes & fees
Apr 18 - Apr 19
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! (2,052 reviews)
5 minutes from the airport
"My husband and I had a lay over in Chicago. It was simple to get to the hotel. I wished we could get a a hold of someone on the phone for a shuttle but that was too difficult. Luckily the airport workers showed us how to get to the hotel from the airport."

Reviewed on Apr 13, 2025

Hilton Chicago O'Hare Airport
Claridge House
Claridge House
4 out of 5
1244 N Dearborn Parkway, Chicago, IL
The price is $139 per night from Apr 20 to Apr 21
$139
includes taxes & fees
Apr 20 - Apr 21
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! (1,238 reviews)
"Great staff, clean property."

Reviewed on Apr 13, 2025

Claridge House
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
The price is $204 per night from May 1 to May 2
$204
includes taxes & fees
May 1 - May 2
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! (1,092 reviews)
"The Corner King Suit was beautiful and the hotel itself is very well located. Everything was pretty walkable. There are tons of food options all around and surprisingly the area was rather quiet"

Reviewed on Apr 14, 2025

Thompson Chicago, by Hyatt
Viceroy Chicago
Viceroy Chicago
4.5 out of 5
1118 North State Street, Chicago, IL
The price is $306 per night from Apr 20 to Apr 21
$306
includes taxes & fees
Apr 20 - Apr 21
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! (1,007 reviews)
Great staff
"Everyone was amazing from start to finish. We were there for a wedding and the staff was kind and helpful. Helped us with a photo moment and the valet parking really ended up being worth it. Our room was cozy. Especially enjoyed the comfortable bed and the size of the bathroom for getting wedding ..."

Reviewed on Apr 13, 2025

Viceroy Chicago
See all 2,328 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.