$56 Cheap Flights to Highland Park, IL

Flights to Highland Park at a glance

Traveling to Highland Park is easy—explore a range of options, including full-service and budget airlines. Compare travel times to find flights to Highland Park that fit your budget and schedule, making it simple to plan your adventures through the city's renowned attractions and neighborhoods.

• Major airport near Highland Park: O'Hare International Airport (ORD)
• Flights per week: 8,150+ flights arriving at Highland Park airport
• Number of airlines that fly to Highland Park: around 75+ carriers

Popular airport near Highland Park

Highland Park is a vibrant city perfect for family-friendly outdoor adventures and entertainment getaways. Visitors are drawn to its appealing blend of outdoor activities, family fun, urban experiences, sports, and business opportunities. The area is conveniently served by a major airport, making travel seamless for those exploring Highland Park.

• O'Hare International Airport (ORD): Situated in Cook County, Illinois, approximately 15 miles from Highland Park, this airport is a major hub for both domestic and international travel. It provides connections to over 285 domestic cities and more than 315 international locations. Passengers can opt for upgraded services such as first class, premium economy, and business class seating for enhanced comfort, depending on the airlines and routes chosen. Key airlines operating at this airport include American Airlines, United, and Frontier Airlines.

Top routes to Highland Park

• New York (JFK/LGA) to Highland Park (ORD), with one-way airfare from around $45
• Los Angeles (LAX) to Highland Park (ORD), with one-way airfare from around $80
• Boston (BOS) to Highland Park (ORD), with one-way flight options from around $60
• Orlando (MCO) to Highland Park (ORD), with one-way fares starting at around $50
• Las Vegas (LAS) to Highland Park (ORD), with one-way airfare from around $60

Cheapest routes to Highland Park

• Burlington (BRL/BTV) to Highland Park (ORD), with cheap one-way fares from around $40
• New York (JFK/LGA) to Highland Park (ORD), with low-cost one-way tickets from around $45
• Atlanta (ATL) to Highland Park (ORD), with cheap one-way fares from around $45
• Fort Lauderdale (FLL) to Highland Park (ORD), with affordable one-way prices from around $45
• Nashville (BNA) to Highland Park (ORD), with affordable one-way prices from around $45

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Highland Park

• American Airlines: Operating flights to O'Hare International Airport (ORD), this airline represents roughly 36% of arrivals to Highland Park. The typical one-way fare hovers around $390, with premium service options that may include premium economy, business, and first class depending on the route.
• United: Also servicing O'Hare International Airport (ORD), United accounts for nearly 35% of arrivals to Highland Park. One-way fares average about $380, with premium service options such as premium economy, business, and first class available based on the route.
• Delta: Connecting to O'Hare International Airport (ORD), Delta makes up about 8% of arrivals to Highland Park. The average one-way fare is around $360, and travelers can choose from premium economy, business, and first class depending on their selected route.
• Frontier Airlines: Providing service to O'Hare International Airport (ORD), Frontier Airlines contributes approximately 3% of arrivals to Highland Park. Passengers can expect an average one-way fare of about $160, making it a budget-friendly choice.
• Southwest Airlines: Flying into O'Hare International Airport (ORD), Southwest Airlines accounts for approximately 2% of arrivals to Highland Park. The average one-way fare is around $230, offering travelers a competitive option for their journeys.

Best time to fly to Highland Park

The most popular months for travelers to fly to Highland Park are January, March, and April, when peak temperatures in Highland Park can reach up to 44.8°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 66.2°F and typically the lowest average one-way fare (around $205), roughly 10% cheaper than the yearly average. Looking for additional cheaper months to fly? October, November, and May offer average one-way fares roughly ranging from $206 to $218, making them good options for flexible travelers.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Highland Park

Getting some of the best deals on flights to Highland Park is all about timing and flexibility. Here are some key tips to help you save:

1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Highland Park hotel and flight deals.
4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
5. Earn miles—you can earn airline miles when you book your Highland Park flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Highland Park

Highland Park welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Highland Park efficiently:

• Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away by walking, while Rosemont Station, a train station, is about 2.2 miles from the airport and is best reached by car.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Highland Park, with private rides that can be arranged in advance.
• Car rental: Renting a car in Highland Park is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Highland Park on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay in and around Highland Park

• Chicago: A vibrant metropolis, Highland Park is situated in Chicago, a hub for family activities, outdoor adventures, and city experiences. Visitors to Chicago can enjoy a variety of attractions, including shopping areas, renowned theaters, and arena entertainment. Local landmarks such as the Griffin Museum of Science and Industry cater to culture enthusiasts, while the iconic 875 North Michigan Avenue offers stunning city views. Whether you're wandering along Michigan Avenue or exploring urban parks, Chicago provides an unforgettable urban experience.
• Hawthorn Woods: Located 15 miles drive away from Highland Park, Hawthorn Woods is a charming village perfect for family outings and outdoor fun. This area features excellent golf courses and shopping centers. Key attractions include Six Flags Great America, ideal for a day of excitement, and the Schaumburg Convention Center, which serves as an important event venue. The Lake County Fairgrounds also hosts various events, making this destination a lively spot for families and outdoor lovers alike.
• Forest Lake: Forest Lake is located 17 miles drive away from Highland Park and offers a blend of family-friendly and business experiences. Visitors can explore shopping centers, educational venues, and serene parks. Notable highlights include Six Flags Great America for thrill-seekers and the Schaumburg Convention Center for conferences. Bristol Trails Park invites families to enjoy outdoor activities in a peaceful urban setting, making it an appealing stop for those looking to relax or socialize.

Tips for short-haul flights to Highland Park

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

• Pack light and skip checked bags—when flying with budget airlines, it's often more economical to travel with just a carry-on. Maximize space by using mini toiletries, wearing your bulkiest clothing, and planning your outfits wisely. This approach also helps you avoid the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights do not provide in-flight entertainment. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself occupied. Remember to charge your devices fully before you board.
• Arrive at the airport in plenty of time—even for short or domestic flights, it's advisable to arrive at least 1.5 to 2 hours prior to departure, taking traffic and security lines into account.
• Bring your own snacks and water—pack your favorite snacks and a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Highland Park

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

• Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines often allow free seat selection once online check-in begins, typically 24–48 hours before your flight. Some airlines may permit seat selection even earlier.
• Arrive at the airport in plenty of time—make sure to arrive at least 3 hours before departure for international flights to accommodate check-in, security, and immigration procedures.
• Relax at the airport—if you find yourself with extra time, take the opportunity to explore the shops, grab a coffee, or unwind at the gate or in a departure lounge if you have access. Free and accessible airport Wi-Fi is usually available.
• Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and adjusting your sleep schedule to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time at your arrival location to help mitigate jet lag.

Tips to find the cheapest flights to Highland Park

The cheapest day to fly

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.

The cheapest month to fly

October is the cheapest month to fly to Highland Park. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Highland Park. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Highland Park, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Highland Park

The lowest price for round-trip flights to Highland Park in 2026 starts from $118, while one-way tickets start from from $56. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Highland Park. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Highland Park

Frontier Airlines, American Airlines, Southwest Airlines, United, Delta are just some of the airlines that can typically offer cheap tickets to Highland Park. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Highland Park and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Highland Park, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Highland Park. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Highland Park plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Highland Park

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Highland Park.

Stopover savings

The cheapest tickets to Highland Park are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Highland Park. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Highland Park for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Highland Park. Simply download the free Expedia app to your smart device and activate Highland Park flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Highland Park. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.