$21 Cheap Flights to Highland Park, IL

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How much is the cheapest flight to Highland Park?

Prices were available within the past 7 days and start at $21 for one-way flights and $41 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Sep 10 - Tue, Sep 10
LGA
LaGuardia
ORD
O'Hare Intl.
$41 Roundtrip, found 6 hours ago
$41
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Sep 10 from LaGuardia to O'Hare Intl., returning Tue, Sep 10, priced at $41 found 6 hours ago
Spirit Airlines
Tue, Sep 10 - Wed, Sep 11
EWR
Liberty Intl.
ORD
O'Hare Intl.
$70 Roundtrip, just found
$70
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Sep 10 from Liberty Intl. to O'Hare Intl., returning Wed, Sep 11, priced at $70 just found
Spirit Airlines
Tue, Aug 27 - Wed, Aug 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 1 hour ago
$109
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Los Angeles Intl. to O'Hare Intl., returning Wed, Aug 28, priced at $109 found 1 hour ago
Frontier Airlines
Tue, Sep 10 - Sat, Sep 14
LGA
LaGuardia
ORD
O'Hare Intl.
$110 Roundtrip, found 6 hours ago
$110
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Sep 10 from LaGuardia to O'Hare Intl., returning Sat, Sep 14, priced at $110 found 6 hours ago
United
Tue, Sep 10 - Wed, Sep 11
EWR
Liberty Intl.
ORD
O'Hare Intl.
$119 Roundtrip, just found
$119
Roundtrip
just found
Select United flight, departing Tue, Sep 10 from Liberty Intl. to O'Hare Intl., returning Wed, Sep 11, priced at $119 just found

Find Your Flights to Highland Park CHI

Cheap flights to Highland Park (CHI)

Get started finding a cheap flight to Highland Park on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Highland Park.

Roundtrip prices range from $41 - $119, and one-ways to Highland Park start as low as $21.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

Airlines that fly to Highland Park (CHI)

You have several options for which airline you choose to travel with to Highland Park. There are 10 airlines flying into CHI: Spirit Airlines, Frontier Airlines, United. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check a bag or bring a carry-on, check whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked/carry-on baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programs may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel in one online platform.

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at the optimal times. Airfare to Highland Park (CHI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for roundtrips to CHI in September and in August for one-ways.

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24-hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Frequently asked questions

How do I find cheap flights to Highland Park that have flexible change policies?
By using our handy “No change fee” filter, that’s how. All you have to do is enter your travel dates, click “Search,” then click the checkbox directly under the “Flexible change policies” heading (it’s on the left of your screen). Expedia makes it easy to find low-cost, flexible fares to Highland Park.
What is the name of the airport in Highland Park?
If you’re heading to Highland Park, you have a number of choices. O’Hare Intl. Airport (ORD) is the main one, followed by Midway Intl. Airport (MDW).
How far is ORD from central Highland Park?
If you plan on staying in central Highland Park, it’s a smart idea to organize how you’ll get into the city before you land. The downtown area is 25 mi from ORD.
How can I book the cheapest flight to Highland Park?
If you’d like to have some extra cash to play with during your trip to Highland Park, avoid booking at the last minute. Prices are generally more expensive as the departure date nears. Research your airport options as well. Airfares vary based on which airport you land at. Make sure you compare prices across airlines and if possible, keep your travel dates flexible. Lastly, be ready to book fast. If you come across an incredible deal, grab it! Currently, one of the cheapest one-way tickets to Highland Park costs $19. This is for a flight that leaves from Charlotte in June.
Which day of the week is the best day to buy a plane ticket to Highland Park?
According to our research, Sundays are the best day to purchase plane tickets. Prices do fluctuate with demand though, so it’s a good idea to be checking prices regularly. After another insider tip? Research fares to Highland Park as soon as you have your travel dates and be ready to book when you spot a bargain. The optimal booking window ranges from 21 days to about 45 days out from takeoff, so the earlier you begin looking, the greater the odds of scoring a terrific deal! Savings are subject to change and may vary depending on selections made.
What airport is best to fly into Highland Park?
There are two major airports that service Highland Park. O’Hare Intl. Airport (ORD) is about 25 mi from the central area, while MDW is around 45 mi away. After you take a look at prices and lock in a place to stay, you’ll have a better idea of which one you should fly into.
Which airlines fly to Highland Park?
From takeoff to landing, you can look forward to a comfortable journey with United Airlines. One of 47 airlines that connects Highland Park with 233 airports across the world, it operates the biggest number of services between New York and Highland Park. American Airlines is also a popular option with travelers.
How many nonstop flights are there to Highland Park?
With approximately 7,977 nonstop flights running each week, you’ll be touching down in Highland Park before you have time to say, “Are we there yet?”
Where are the most popular flights to Highland Park departing from?
Travelers often depart from New York, Dallas and Phoenix airports when flying to Highland Park.
Do you have any tips for my flight to Highland Park?

  • Get your trip off to a promising start by being well prepared. Pack your passport or ID, travel documents and medications first. Next, think about downloading your favorite series on your tablet or phone for a binge session sans guilt. Or, toss in that fantasy bestseller you haven’t had time to read. Lastly, a few snacks and a soft neck pillow will help make the trip as comfy as possible.
  • Remember that there’s also a list of prohibited items for your hand luggage which can differ between carriers and flight routes. Generally, avoid carrying anything sharp, flammable or explosive. This includes things like knives, razor blades, flares and aerosol cans. Sports equipment like baseball bats, tennis rackets and objects considered weapons, such as batons and swords, are also banned from the cabin.

What to wear on a flight:

  • Whether traveling long or short-haul, wearing layers will help you stay comfortable. Choose loose, natural fabrics that will keep you cool and pack a pullover for any in-flight temperature changes. Keep your feet happy in a pair of flat shoes or sneakers.
  • The condition known as deep vein thrombosis (DVT) is a risk on long-haul flights. It’s the result of blood clotting due to poor circulation and inactivity. Wandering up and down the aisle and doing leg and foot stretches while seated can prevent it developing. Wearing compression tights or socks can also help to lessen your risk.

How can I get a cheap last-minute flight to Highland Park?
If you want to land a cheap last-minute flight to Highland Park, being flexible is key. If you can, have a bit of wiggle room with the dates you can travel. It will also help to keep your options open with your airports, airline choice, flight times and possible stops or layovers.
Where can I learn more about changing or canceling my flight to Highland Park?
Most flights are free to cancel within 24 hours of making the reservation. However, some flights are non-refundable, and you may receive a flight credit from the airline to use for a future booking. For more information, please visit our Customer Service Portal.
Flights to Highland Park information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$50

Trending flights to Highland Park

Prices were available within the past 7 days and start at $21 for one-way flights and $41 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Sep 10 - Tue, Sep 10
LGA
LaGuardia
ORD
O'Hare Intl.
$41 Roundtrip, found 6 hours ago
$41
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Sep 10 from LaGuardia to O'Hare Intl., returning Tue, Sep 10, priced at $41 found 6 hours ago
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