$26 Cheap Flights to Highwood, IL

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Featured airlines

Featured Airlines: American Airlines, United Airlines, Delta, Spirit, JetBlue, Frontier, Air India, Hawaiian Airlines and Qatar Airways

How much is the cheapest flight to Highwood?

Prices were available within the past 7 days and start at $26 for one-way flights and $51 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Sep 10 - Wed, Sep 11
LGA
LaGuardia
ORD
O'Hare Intl.
$51 Roundtrip, found 2 hours ago
$51
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Sep 10 from LaGuardia to O'Hare Intl., returning Wed, Sep 11, priced at $51 found 2 hours ago
Spirit Airlines
Thu, Sep 5 - Wed, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Sep 5 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Sep 11, priced at $59 just found
Frontier Airlines
Sat, Sep 7 - Sat, Sep 7
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$63 Roundtrip, found 5 hours ago
$63
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Sep 7 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Sep 7, priced at $63 found 5 hours ago
Spirit Airlines
Tue, Sep 10 - Wed, Sep 11
EWR
Liberty Intl.
ORD
O'Hare Intl.
$85 Roundtrip, found 3 hours ago
$85
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Sep 10 from Liberty Intl. to O'Hare Intl., returning Wed, Sep 11, priced at $85 found 3 hours ago
Spirit Airlines
Tue, Aug 27 - Tue, Aug 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 2 hours ago
$109
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Los Angeles Intl. to O'Hare Intl., returning Tue, Aug 27, priced at $109 found 2 hours ago

Find Your Flights to Highwood ORD

Cheap flights to Highwood (ORD)

Get started finding a cheap flight to Highwood 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 Highwood.

Roundtrip prices range from $51 - $109, and one-ways to Highwood start as low as $26.

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 Highwood (ORD)

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

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 Highwood (ORD) varies throughout the year based on seasonal demand. You’ll see the lowest rates for roundtrips to ORD 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 Highwood that have flexible change policies?
It’s as easy as can be with Expedia. Step 1: Enter your preferred travel dates and click on “Search.” Second step: Check “No change fee” directly below the “Flexible change policies” filter to the left of your screen. Step 3. Bag your flexible and cheap fare to Highwood.
How far is ORD from central Highwood?
ORD is 25 mi from downtown Highwood, so prepare yourself for a bit of a journey into the city.
How can I book the cheapest flight to Highwood?
To boost your chances of scoring the cheapest flight, enter your travel details into the search bar, then filter the results by airline, arrival and departure times, and number of stops. Also compare the prices of flying into and out of nearby airports if possible. Timing is crucial when it comes to clinching a bargain — book domestic flights at least four weeks out and international flights around six months in advance to save 10% on average. And if you stumble on an incredible deal, book it before it’s gone! One of the cheapest flights to Highwood right now is $19, departing Charlotte in June. Wherever you’re flying in from, Expedia will help get you to Highwood for the cheapest price possible.
Which day of the week is the best day to buy a plane ticket to Highwood?
Sunday is the cheapest day of the week to buy a plane ticket. But that’s not the only way to score a fantastic deal. Looking for tickets and being ready to buy several weeks before your departure date will also pay off. Research shows that the optimal booking window ranges from 21 days to about 45 days prior to departure. Settled on your travel dates to Highwood months ahead of time? Monitor when airlines first release their tickets as often these are the best prices available. Savings are subject to change and may vary depending on selections made.
What airport is best to fly into Highwood?
Pass through the exit of O’Hare Intl. Airport (ORD) and your Highwood adventure will have begun! The city’s main airport, it’s located 25 mi from the downtown area.
How many nonstop flights are there to Highwood?
With approximately 6,388 nonstop flights running every week, you’ll be touching down in Highwood before you can ask, “Are we there yet?”
Where are the most popular flights to Highwood departing from?
A large number of flights to Highwood depart from New York, Dallas and Phoenix airports.
Do you have any tips for my flight to Highwood?

  • Wherever you’re traveling, flying can be a wonderful experience if you come well prepared. First, pack your passport (or a valid ID), travel documents and medications. Next, throw in a little extra in-flight entertainment to help make the time fly by. The latest bestseller and a tablet filled with your favorite series are some fantastic options. If you’re hoping to catch some z’s, a comfortable neck pillow and noise-canceling headphones will also come in handy.
  • Remember that there’s also a list of prohibited items for your hand luggage which can differ between airlines. Generally, avoid carrying anything sharp, explosive or flammable. This includes things like razor blades, pocket knives, aerosol cans and flares. Sporting equipment like ski poles, baseball bats and objects that could harm passengers, such as swords and batons, are also banned from the cabin.

What to wear on a flight:

  • Whether traveling short or long-haul, wearing layers will help you stay comfortable. Choose loose, breathable fabrics that will keep you fresh and pack a pullover for any changes in cabin temperatures. Keep your feet happy in a pair of sneakers or closed-toe shoes.
  • Lessen your risk of developing deep vein thrombosis (DVT), a blood clotting condition which can be caused by sitting for lengthy periods, by regularly walking around the cabin. Alternatively, do some gentle foot and leg exercises in your seat. If you’re at higher risk of developing DVT, consider wearing compression socks or tights.

How can I get a cheap last-minute flight to Highwood?
Finding a cheap, spur-of-the-moment flight to Highwood is as simple as being flexible with your travel plans. Have some leeway with your choice of carrier, flight times and travel dates. If your destination has a few airports, compare the prices of jetting into each of them for the best deal on your fare.
Where can I learn more about changing or canceling my flight to Highwood?
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 Highwood information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
$42

Trending flights to Highwood

Prices were available within the past 7 days and start at $26 for one-way flights and $51 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Sep 10 - Wed, Sep 11
LGA
LaGuardia
ORD
O'Hare Intl.
$51 Roundtrip, found 2 hours ago
$51
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Sep 10 from LaGuardia to O'Hare Intl., returning Wed, Sep 11, priced at $51 found 2 hours ago
*Available to One Key members.