Search Cheap Flights to
Highland Park

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Highland Park Flights as Low as $97

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

United
Mon, Nov 10 - Thu, Nov 13
BOS
Logan Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select United flight, departing Mon, Nov 10 from Logan Intl. to O'Hare Intl., returning Thu, Nov 13, priced at $97 found 1 day ago
United
Wed, Sep 3 - Mon, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select United flight, departing Wed, Sep 3 from Logan Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $99 found 1 day ago
JetBlue Airways
Wed, Sep 3 - Mon, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 3 from Logan Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $109 found 1 day ago
United
Wed, Sep 3 - Mon, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Select United flight, departing Wed, Sep 3 from Logan Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $111 found 1 day ago
JetBlue Airways
Thu, Sep 4 - Thu, Sep 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Sep 4 from Logan Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $119 found 2 days ago
American Airlines
Wed, Sep 3 - Mon, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Sep 3 from Logan Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $121 found 1 day ago
Delta
Sat, Aug 30 - Sun, Aug 31
BOS
Logan Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 4 days ago
$138
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 30 from Logan Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $138 found 4 days ago
Spirit Airlines
Sat, Aug 16 - Tue, Aug 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 4 days ago
$141
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Los Angeles Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $141 found 4 days ago
Frontier Airlines
Mon, Sep 29 - Sun, Oct 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$144 Roundtrip, found 22 hours ago
$144
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Los Angeles Intl. to O'Hare Intl., returning Sun, Oct 12, priced at $144 found 22 hours ago
Bargain Flight
Thu, Sep 4 - Thu, Sep 4
MEM
Memphis Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 3 hours ago
$153
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Thu, Sep 4 from Memphis Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $153 found 3 hours ago
Delta
Tue, Oct 14 - Tue, Oct 21
MEM
Memphis Intl.
MDW
Midway Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 14 from Memphis Intl. to Midway Intl., returning Tue, Oct 21, priced at $197 found 3 days ago
Delta
Sat, Oct 25 - Sat, Oct 25
LAX
Los Angeles Intl.
MDW
Midway Intl.
$211 Roundtrip, found 8 hours ago
$211
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Oct 25 from Los Angeles Intl. to Midway Intl., returning Sat, Oct 25, priced at $211 found 8 hours ago
Alaska Airlines
Sat, Nov 15 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 2 hours ago
$216
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 19, priced at $216 found 2 hours ago
Sun Country Airlines
Fri, Sep 26 - Mon, Sep 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 3 days ago
$277
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Fri, Sep 26 from Los Angeles Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $277 found 3 days ago
Delta
Wed, Aug 20 - Tue, Aug 26
BOS
Logan Intl.
MDW
Midway Intl.
$279 Roundtrip, found 2 days ago
$279
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 20 from Logan Intl. to Midway Intl., returning Tue, Aug 26, priced at $279 found 2 days ago
Hawaiian Airlines
Mon, Nov 17 - Sat, Nov 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$348 Roundtrip, found 1 day ago
$348
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Mon, Nov 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 22, priced at $348 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 November, 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 $97, 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 $97 right now, why wait?

Highland Park Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$97

Last Minute Hotel Deals in Highland Park

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! (2,072 reviews)
"Overall a great hotel for my needs. Had my flight come in late at night and next segment early in am."

Reviewed on Jul 23, 2025

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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 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! (1,786 reviews)
"Good stop for a quick Chicago visit"

Reviewed on Jul 25, 2025

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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
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! (2,318 reviews)
"Our stay at the Crowne Plaza Rosemont was nice. It was a business trip for a conference. The elevators had some issues and with so many people in for the conference it made it a bit of a “log jam” at times. The staff was very friendly. The location was perfect with several restaurants within walking ..."

Reviewed on Jul 20, 2025

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Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
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 ...
8.8/10 Excellent! (1,264 reviews)
"Lovely hotel with old world charm. Great location for dining and shopping. Very comfortable beds and friendly staff."

Reviewed on Jul 22, 2025

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Claridge House
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
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! (1,094 reviews)
"Great if you need to get to airport quickly and 50 minutes from the city."

Reviewed on Jul 21, 2025

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Marriott Chicago O'Hare
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,050 reviews)
Very Good
"Missed my train and ended up staying a night at the Ambassador. It was a good experience."

Reviewed on Jul 24, 2025

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The Chicago Hotel Collection Ambassador Gold Coast
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! (1,182 reviews)
"Loved the location you will never find anything better than this..."

Reviewed on Jul 21, 2025

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Thompson Chicago, by Hyatt
Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

3 out of 5
6810 Mannheim Rd, Rosemont, IL
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.2/10 Very Good! (3,024 reviews)
"."

Reviewed on Jul 22, 2025

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Hyatt Place Chicago/O'Hare Airport
See all 2,562 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.