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Highland Park

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Highland Park Flights as Low as $76

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

Frontier Airlines
Tue, Aug 11 - Wed, Aug 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$76 Roundtrip, found 7 hours ago
$76
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Aug 12, priced at $76 found 7 hours ago
Frontier Airlines
Mon, Sep 14 - Tue, Sep 15
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$108 Roundtrip, found 4 hours ago
$108
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Sep 14 from George Bush Intercontinental to O'Hare Intl., returning Tue, Sep 15, priced at $108 found 4 hours ago
Frontier Airlines
Wed, Aug 19 - Wed, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 15 hours ago
$124
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 19, priced at $124 found 15 hours ago
Frontier Airlines
Tue, Sep 22 - Tue, Oct 13
IAH
George Bush Intercontinental
MDW
Midway Intl.
$169 Roundtrip, found 4 days ago
$169
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from George Bush Intercontinental to Midway Intl., returning Tue, Oct 13, priced at $169 found 4 days ago
Frontier Airlines
Sat, Aug 22 - Sat, Sep 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 19 hours ago
$171
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Aug 22 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 5, priced at $171 found 19 hours ago
Bargain Flight
Thu, Nov 26 - Thu, Dec 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$184 Roundtrip, found 9 hours ago
$184
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Thu, Nov 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Dec 17, priced at $184 found 9 hours ago
American Airlines
Thu, Oct 22 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $197 found 4 hours ago
Delta
Wed, Nov 4 - Wed, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Nov 4 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $197 found 4 hours ago
Delta
Tue, Sep 22 - Tue, Sep 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$220 Roundtrip, found 4 days ago
$220
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 22 from Los Angeles Intl. to Midway Intl., returning Tue, Sep 29, priced at $220 found 4 days ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 5 days ago
$250
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $250 found 5 days ago
American Airlines
Mon, Sep 14 - Thu, Sep 17
IAH
George Bush Intercontinental
RFD
Greater Rockford
$288 Roundtrip, found 6 days ago
$288
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 14 from George Bush Intercontinental to Greater Rockford, returning Thu, Sep 17, priced at $288 found 6 days ago
American Airlines
Fri, Aug 14 - Sun, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$444 Roundtrip, found 9 hours ago
$444
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Fri, Aug 14 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sun, Aug 16, priced at $444 found 9 hours ago
Icelandair
Tue, Sep 1 - Mon, Sep 21
VCE
Marco Polo
ORD
O'Hare Intl.
$568 Roundtrip, found 4 days ago
$568
Roundtrip
found 4 days ago
Select Icelandair flight, departing Tue, Sep 1 from Marco Polo to O'Hare Intl., returning Mon, Sep 21, priced at $568 found 4 days ago
Condor
Thu, Aug 13 - Sat, Aug 22
VCE
Marco Polo
MDW
Midway Intl.
$1,049 Roundtrip, found 17 hours ago
$1,049
Roundtrip
found 17 hours ago
Select Condor flight, departing Thu, Aug 13 from Marco Polo to Midway Intl., returning Sat, Aug 22, priced at $1,049 found 17 hours ago
TAP Portugal
Fri, Oct 2 - Sat, Oct 17
XVY
Mestre Rail Station
ORD
O'Hare Intl.
$1,180 Roundtrip, found 4 hours ago
$1,180
Roundtrip
found 4 hours ago
Select TAP Portugal flight, departing Fri, Oct 2 from Mestre Rail Station to O'Hare Intl., returning Sat, Oct 17, priced at $1,180 found 4 hours ago
TAP Portugal
Fri, Oct 2 - Sat, Oct 17
XVQ
Santa Lucia Rail Station
ORD
O'Hare Intl.
$1,180 Roundtrip, found 4 hours ago
$1,180
Roundtrip
found 4 hours ago
Select TAP Portugal flight, departing Fri, Oct 2 from Santa Lucia Rail Station to O'Hare Intl., returning Sat, Oct 17, priced at $1,180 found 4 hours 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 August, 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 15 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 $76, 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 $76 right now, why wait?

Highland Park Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$166

Last Minute Hotel Deals in Highland Park

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,961 reviews)
"I was double charged. Still trying to get resolved!!"

Reviewed on Aug 9, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,379 reviews)
"Go place to stay if your traveling and have a connection next day. Also very safe! A bit expensive especially the valet parking"

Reviewed on Aug 9, 2026

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Hilton Chicago O'Hare Airport
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 business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
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Hyatt Regency O'Hare Chicago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
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Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
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Holiday Inn Chicago O'Hare – Rosemont by IHG
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
7.8/10 Good! (3,130 reviews)
"The front desk staff"

Reviewed on Aug 9, 2026

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Comfort Suites Chicago O'Hare Airport
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

4.5 out of 5
5300 N River Rd Rosemont IL
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
9.4/10 Exceptional! (2,159 reviews)
"excellent hotel near o'hare. rooms are clean and modern. appreciate the amenities....on site....several restaurants, on-site convenience shop also serving starbucks. Various meeting rooms and an ATM.... especially appreciated the round the clock shuttle to O'Hare. Service was exceptional."

Reviewed on Aug 9, 2026

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Loews Chicago O'Hare Hotel
Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
5500 N River Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and ...
8.8/10 Excellent! (1,628 reviews)
"I always love staying at this hotel when I come to Chicago!"

Reviewed on Aug 9, 2026

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Embassy Suites by Hilton Chicago O'Hare Rosemont
See all 2,576 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.