Search Cheap Flights to
Highland Park

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Highland Park Flights as Low as $77

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

Delta
Wed, Jul 16 - Tue, Jul 22
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$77 Roundtrip, found 20 hours ago
$77
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jul 16 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $77 found 20 hours ago
Delta
Tue, Jul 8 - Tue, Jul 15
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$79 Roundtrip, found 1 day ago
$79
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 8 from Minneapolis - St. Paul Intl. to Midway Intl., returning Tue, Jul 15, priced at $79 found 1 day ago
Frontier Airlines
Wed, May 28 - Tue, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 6 days ago
$94
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $94 found 6 days ago
Spirit Airlines
Mon, Jun 9 - Sat, Jun 14
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 5 days ago
$102
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Jun 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jun 14, priced at $102 found 5 days ago
Frontier Airlines
Mon, Jun 9 - Sat, Jun 14
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 5 days ago
$110
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jun 14, priced at $110 found 5 days ago
Frontier Airlines
Tue, Jul 29 - Tue, Aug 5
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$126 Roundtrip, found 2 days ago
$126
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 29 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Aug 5, priced at $126 found 2 days ago
Sun Country Airlines
Wed, Jul 16 - Sat, Jul 19
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 4 hours ago
$127
Roundtrip
found 4 hours ago
Select Sun Country Airlines flight, departing Wed, Jul 16 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sat, Jul 19, priced at $127 found 4 hours ago
Frontier Airlines
Sun, Jun 15 - Thu, Jun 19
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$136 Roundtrip, found 14 hours ago
$136
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, Jun 15 from Raleigh - Durham Intl. to O'Hare Intl., returning Thu, Jun 19, priced at $136 found 14 hours ago
United
Wed, Jul 16 - Wed, Jul 16
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 20 hours ago
$137
Roundtrip
found 20 hours ago
Select United flight, departing Wed, Jul 16 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $137 found 20 hours ago
American Airlines
Wed, Jul 16 - Sat, Jul 19
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Jul 16 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sat, Jul 19, priced at $157 found 4 hours ago
Delta
Wed, Jun 25 - Sat, Jun 28
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jun 25 from Love Field to Midway Intl., returning Sat, Jun 28, priced at $197 found 4 days ago
Delta
Wed, Jul 9 - Tue, Jul 15
DAL
Love Field
ORD
O'Hare Intl.
$200 Roundtrip, found 18 hours ago
$200
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Jul 9 from Love Field to O'Hare Intl., returning Tue, Jul 15, priced at $200 found 18 hours ago
Contour Airlines
Thu, Jul 10 - Sun, Jul 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select Contour Airlines flight, departing Thu, Jul 10 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $209 found 5 days ago
JetBlue Airways
Mon, Sep 15 - Tue, Sep 23
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$213 Roundtrip, found 21 hours ago
$213
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Mon, Sep 15 from Raleigh - Durham Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $213 found 21 hours ago
Frontier Airlines
Wed, May 28 - Tue, Jun 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$214 Roundtrip, found 4 days ago
$214
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Los Angeles Intl. to Midway Intl., returning Tue, Jun 3, priced at $214 found 4 days ago
Frontier Airlines
Mon, May 19 - Sat, May 24
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 19 from Raleigh - Durham Intl. to Midway Intl., returning Sat, May 24, priced at $240 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 July, 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 $77, 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 $77 right now, why wait?

Highland Park Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$107

Last Minute Hotel Deals in Highland Park

Ambassador Hotel Chicago
Ambassador Hotel Chicago
4 out of 5
1301 N State Pkwy, Chicago, IL
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 ...
8.4/10 Very Good! (1,013 reviews)
"Loved the hotel and location!!!"

Reviewed on May 13, 2025

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Ambassador Hotel Chicago
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! (1,564 reviews)
"Good location near the airport. Rooms were great. Breakfast bar was great"

Reviewed on May 14, 2025

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Hyatt Regency O'Hare Chicago
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! (1,108 reviews)
"It’s nice"

Reviewed on May 9, 2025

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Thompson Chicago, by Hyatt
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! (2,048 reviews)
"Staff was friendly, centrally located in Asakusa"

Reviewed on May 14, 2025

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Hilton Chicago O'Hare Airport
La Quinta by Wyndham Chicago O'Hare Airport
La Quinta by Wyndham Chicago O'Hare Airport
2.5 out of 5
6860 Mannheim Rd, Rosemont, IL
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! (1,426 reviews)
"Not a bad facility, room was good. Hotel is not clearly marked on outside. Both my uber and door dash drivers had difficulty finding it. Outside looked rough and unkept. Inside was better. Not flexible as I wanted to add my Wyndham number they wouldn’t do it. Plus damn alarm went off at 0500 in room ..."

Reviewed on May 14, 2025

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La Quinta by Wyndham Chicago O'Hare Airport
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Stay at this 3-star business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,013 reviews)
"Room was big and comfortable"

Reviewed on May 14, 2025

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Hyatt Place Chicago/Hoffman Estates
SpringHill Suites Chicago O'Hare by Marriott
SpringHill Suites Chicago O'Hare by Marriott
3 out of 5
8101 West Higgins Road, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,180 reviews)
"Very nice and clean room. Great price for the room but parking was not included and was expensive with no responsibility for damage. No parking garage but a large parking lot."

Reviewed on May 15, 2025

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SpringHill Suites Chicago O'Hare by Marriott
Four Points by Sheraton Chicago O'Hare Airport
Four Points by Sheraton Chicago O'Hare Airport
3 out of 5
10249 Irving Park Road, Schiller Park, IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant ...
7.4/10 Good! (1,662 reviews)
"I dont know why thry put us,at the very far end of the property. Seemed like not many people there . Wifi was not great way doen at thr end if the hall . Guess i should of mentioned i was disabled. Breakfast here is not included either ."

Reviewed on May 14, 2025

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Four Points by Sheraton Chicago O'Hare Airport
See all 2,339 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.