Search Cheap Flights toHighland Park
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Highland Park Flights as Low as $82
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, May 13 - Tue, May 13
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$82 Roundtrip, found 6 hours ago
$82
Roundtrip
found 6 hours ago
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$96 Roundtrip, found 6 days ago
$96
Roundtrip
found 6 days ago
Thu, May 29 - Mon, Jun 2
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$102 Roundtrip, found 13 hours ago
$102
Roundtrip
found 13 hours ago
Tue, May 13 - Sat, May 24
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$103 Roundtrip, found 10 hours ago
$103
Roundtrip
found 10 hours ago
Tue, May 27 - Mon, Jun 2
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$104 Roundtrip, found 13 hours ago
$104
Roundtrip
found 13 hours ago
Wed, May 14 - Wed, May 21
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$110 Roundtrip, found 10 hours ago
$110
Roundtrip
found 10 hours ago
Fri, May 30 - Tue, Jun 3
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$112 Roundtrip, found 13 hours ago
$112
Roundtrip
found 13 hours ago
Thu, May 29 - Mon, Jun 2
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$114 Roundtrip, found 13 hours ago
$114
Roundtrip
found 13 hours ago
Wed, May 28 - Wed, Jun 4
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$121 Roundtrip, found 6 days ago
$121
Roundtrip
found 6 days ago
Tue, May 27 - Sat, May 31
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$122 Roundtrip, found 13 hours ago
$122
Roundtrip
found 13 hours ago
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Wed, Jul 9 - Wed, Jul 23
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Mon, Jun 9 - Thu, Jun 12
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Sat, May 17 - Mon, May 19
TTN
Mercer
ORD
O'Hare Intl.
$214 Roundtrip, found 4 days ago
$214
Roundtrip
found 4 days ago
Sat, May 3 - Sat, May 10
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$411 Roundtrip, found 1 day ago
$411
Roundtrip
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 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 $82, 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 $82 right now, why wait?
Destination airport | O'Hare Intl. |
Destination airport IATA code | ORD |
Roundtrip price | $82 |
Last Minute Hotel Deals in Highland Park
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
The price is $173 per night from May 18 to May 19
$173
includes taxes & fees
May 18 - May 19
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! (1,527 reviews)
"Great classic Hyatt hotel!"
Reviewed on Apr 29, 2025
Ambassador Hotel Chicago
1301 N State Pkwy, Chicago, IL
The price is $164 per night from May 1 to May 2
$164
includes taxes & fees
May 1 - May 2
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! (1,006 reviews)
"They need to improve there capacity to service check-ins, there was a line that went through the entire entrance that took an hour wait to check-in. They said it was always busy like this. They only had two at the front desk. Otherwise very happy stay here, although we lost a couple hours of our ..."
Reviewed on Apr 27, 2025
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
The price is $253 per night from May 24 to May 25
$253
includes taxes & fees
May 24 - May 25
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! (2,033 reviews)
"VERY CONVIENT"
Reviewed on Apr 28, 2025
Claridge House
1244 N Dearborn Parkway, Chicago, IL
The price is $190 per night from May 26 to May 27
$190
includes taxes & fees
May 26 - May 27
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! (1,235 reviews)
"Best room I've ever had at this hotel! I stayed two nights with college friends, checked out of that room, then my husband arrived for the weekend and checked into a different room! Second room, not so good. See that review!"
Reviewed on Apr 23, 2025
Thompson Chicago, by Hyatt
21 East Bellevue, Chicago, IL
The price is $220 per night from May 21 to May 22
$220
includes taxes & fees
May 21 - May 22
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! (1,100 reviews)
"I STAY IN CHICAGO ALL THE TIME FOR WORK EVENTS AND IN ALL MY YEARS HAD NEVER STAYED HERE. IT WAS AWESOME. ROOMS WERE GREAT AND MODERN WITH GREAT VIEWS OF LAKE AND CITY FROM OUR ROOM. HIGHLY RECOMMEND."
Reviewed on Apr 26, 2025
Marriott Chicago O'Hare
8535 West Higgins Road, Chicago, IL
The price is $198 per night from May 23 to May 24
$198
includes taxes & fees
May 23 - May 24
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! (1,019 reviews)
"Nice property. Clean."
Reviewed on Apr 25, 2025
La Quinta by Wyndham Chicago O'Hare Airport
6860 Mannheim Rd, Rosemont, IL
The price is $113 per night from May 12 to May 13
$113
includes taxes & fees
May 12 - May 13
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,376 reviews)
"The hotel was clean and quiet. I had a good night and slept like a baby. I’ve enjoyed the free breakfast buffet as well. Would definitely recommend them"
Reviewed on Apr 28, 2025
Viceroy Chicago
1118 North State Street, Chicago, IL
The price is $329 per night from May 26 to May 27
$329
includes taxes & fees
May 26 - May 27
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! (1,012 reviews)
"Very comfortable stay. Room was beautiful. Rooftop bar was very nice, drinks were good and affordable and the staff were very pleasant."
Reviewed on Apr 23, 2025
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.
Nearby Cities
Popular Flight Routes
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Top Highland Park Hotels
- Hyatt Regency O'Hare Chicago
- Ambassador Hotel Chicago
- Hilton Chicago O'Hare Airport
- Claridge House
- Thompson Chicago, by Hyatt
- Marriott Chicago O'Hare
- Viceroy Chicago
- Chicago Getaway Hostel
- Hyatt Place Chicago/O'Hare Airport
- Super 8 by Wyndham Chicago O'Hare Airport
- The Chicago Hotel Collection River North
- Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
- Hyatt Regency Schaumburg Chicago
- Four Points by Sheraton Chicago O'Hare Airport