$49 Cheap Flights to Highland, IN

Popular airlines to Highland

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How much is the cheapest flight to Highland?

Prices were available within the past 7 days and start at $49 for one-way flights and $98 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
United
American Airlines
Delta
Sun Country Airlines

Alternative airports near Highland

Prices were available within the past 7 days. Prices and availability are subject to change.

What you need to know for your flight to Highland

Flights to Highland at a glance

Traveling to Highland is a breeze—choose between full-service and budget airlines, compare flight durations, and select the option that best fits your budget and itinerary as you plan to explore the city’s renowned attractions and neighborhoods.

  • Major airports near Highland: Midway International Airport (MDW), Midway International Airport (MDW)
  • Closest (typical) airport to Highland: Midway International Airport, MDW (around 22 miles)
  • Flights per week: 1,650+ flights arriving across Highland airports
  • Number of airlines that fly to Highland: around 10+ carriers

Popular airport near Highland

Highland is a vibrant city that offers a perfect blend of outdoor adventures, family-friendly activities, and urban experiences. Visitors come for various reasons, including family, outdoor fun, business, and sports, and the city is conveniently served by a major airport.

  • Midway International Airport (MDW): Situated in Cook County, Illinois, approximately 22 miles from Highland, this airport facilitates both domestic and international travel. It offers connections to over 130 domestic cities and around 30 international destinations. Travelers can opt for premium economy or first-class seating for enhanced comfort, depending on their chosen airline and route. Major carriers like Southwest Airlines, Frontier Airlines, and Delta operate from this bustling hub.

Top routes to Highland

  • Atlanta (ATL) to Highland (MDW), with one-way flight options from around $40
  • Orlando (MCO) to Highland (MDW), with one-way airfare from around $45
  • Dallas (DFW/DAL) to Highland (MDW), with one-way airfare from around $35
  • Phoenix (PHX) to Highland (MDW), with one-way tickets available from around $50
  • New York (JFK/LGA) to Highland (MDW), with one-way airfare from around $70

Cheapest routes to Highland

  • Newark (EWR) to Highland (MDW), with affordable one-way prices from around $30
  • Dallas (DFW/DAL) to Highland (MDW), with budget one-way fares from around $35
  • Atlanta (ATL) to Highland (MDW), with low-cost one-way tickets from around $40
  • Minneapolis (MSP) to Highland (MDW), with budget one-way fares from around $40
  • Nashville (BNA) to Highland (MDW), with low-cost one-way tickets from around $40

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

Top airlines with flights to Highland

  • Southwest Airlines: Operating flights to Midway International Airport (MDW), Southwest Airlines represents about 75% of the arrivals to Highland. The typical one-way fare hovers around $210.
  • Delta: Also servicing Midway International Airport (MDW), Delta accounts for roughly 12% of the arrivals to Highland. The average one-way fare is around $230, with premium service options including premium economy and first class depending on the route.
  • Frontier Airlines: With flights to Midway International Airport (MDW), Frontier Airlines makes up approximately 10% of arrivals to Highland. Passengers can expect an average one-way fare of about $160.
  • Volaris: Providing service to Midway International Airport (MDW), Volaris contributes around 2% of arrivals to Highland. The average fare for a one-way ticket is about $270.
  • Porter Airlines: Operating to Midway International Airport (MDW), Porter Airlines represents roughly 1% of arrivals to Highland. The average one-way fare is approximately $190.

Best time to fly to Highland

The most popular months for travelers to fly to Highland are March, April, and August, when peak temperatures in Highland can reach up to 72.7°F in August. If you prefer quieter travel, consider February, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 27.1°F. For better deals, September usually offers the lowest average one-way fare around $165, roughly 10% cheaper than the yearly average. Looking for additional cheaper months to fly? October, August, and February offer average one-way fares of around $172, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January25.5°F (-3.6°C)Light RainMostly CloudyAverage$206
February27.1°F (-2.7°C)Light RainMostly CloudyModerately Low$176
March38.3°F (3.5°C)Light RainMostly CloudyModerately High$211
April48.0°F (8.9°C)Light RainMostly SunnyModerately High$202
May59.5°F (15.3°C)Light RainMostly SunnyModerately Low$177
June69.1°F (20.6°C)Light RainMostly SunnyAverage$184
July73.6°F (23.1°C)Light RainMostly SunnyAverage$185
August72.7°F (22.6°C)Light RainMostly SunnyModerately High$176
September66.7°F (19.3°C)Light RainMostly SunnyAverage$165
October54.7°F (12.6°C)Light RainMostly SunnyAverage$167
November41.9°F (5.5°C)Light RainMostly SunnyAverage$182
December32.7°F (0.4°C)Light RainMostly CloudyModerately Low$187

*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

Getting some of the best deals on flights to Highland 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.*
  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 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

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

  • Public transportation: From Midway International Airport, travelers can find several transport options nearby. Midway Station, a metro station, is just 0.2 miles from the airport and easily accessible on foot. For those needing rail connections, Chicago Ashburn Station is about 4.1 miles away by car, while Lyons Seaport, a seaport, is located approximately 7.2 miles away by car.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Highland, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Highland is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Highland 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 around Highland

  • Gary: Located 7 miles away from Highland, Gary is a vibrant city known for its stunning scenery and adventurous outdoor experiences. Visitors can explore the nearby national and state parks, which offer beautiful dunes and recreational areas. Key attractions include the Griffin Museum of Science and Industry, perfect for families and culture enthusiasts, and the historic Michael Jackson Family Home, providing a glimpse into the life of the legendary artist. Indiana University Northwest is also a noteworthy site, appealing to those interested in education and modern campus life.
  • Lansing: Lansing is located 5 miles away from Highland and offers a delightful mix of family-friendly activities and urban charm. Visitors can enjoy the recreational areas and urban parks, or catch a show at the local theaters. Notable highlights include Centennial Park, a fantastic spot for outdoor activities and family gatherings, and Purdue University Northwest, which adds a modern collegiate vibe to the city. The Griffin Museum of Science and Industry also draws in families eager for a cultural experience.
  • Harvey: Situated 11 miles away from Highland, Harvey is a city that caters to families and outdoor lovers alike. The city features an array of entertainment options, including theaters and arenas for music concerts. Visitors can explore local landmarks such as the Harvey Community Center and the Harvey Public Library, both of which contribute to the city’s civic and cultural fabric. The Griffin Museum of Science and Industry is another popular destination for those looking to engage in enriching experiences while enjoying the city’s urban parks.

Tips for short-haul flights to Highland

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

  • Pack light and skip checked bags—with budget airlines, traveling with just a carry-on is often more cost-effective. Maximize your packing space by using mini toiletries, wearing your bulkiest clothing, and planning your outfits wisely. This strategy also helps you avoid waiting at baggage claim after your flight.
  • Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. To keep yourself entertained, download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Remember to fully charge your devices 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 before your departure, taking into account potential traffic and security lines.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Highland

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

  • Select your seat in advance—for longer flights, choosing your seat ahead of time is essential for comfort. Full-service airlines often provide complimentary seat selection once online check-in begins, typically 24–48 hours before your flight. Some airlines may allow you to select your seat even earlier.
  • Arrive at the airport in plenty of time—aim to arrive at least 3 hours prior to departure for international flights to ensure you have enough time for check-in, security, and immigration processes.
  • 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. Most airports offer free Wi-Fi that you can easily connect to.
  • Adjust to the new time zone mid-flight—begin syncing your body clock by setting your watch and adjusting your sleep schedule to align with your destination's time zone. Try to rest or stay awake during the flight according to the local time at your arrival point to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Highland?
The cheapest month to fly to Highland is July when demand is low. Off-peak months are usually when you'll find cheap flights. To keep costs down, avoid flying during school breaks and major holidays.
Which US cities have the cheapest flights to Highland?
Land cheap flights to Highland from New York, Washington and Dallas. These cities usually offer the best fares to this unique destination. But remember that seasonality, demand and stopovers will also have an influence on rates, so stay flexible and book when you see a bargain.
Which US cities fly direct to Highland?
Take your pick of 150 US cities with direct flights to Highland. While booking on Expedia, check "Direct flights only" to find nonstop itineraries. Fly to Highland from any of these top cities:

  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix

How to find a cheap flight to Highland?
If you're looking for cheap flights to Highland, consider low-season travel. Booking in advance may also save you money. Or, fly on a different day — flights on a Thursday are on average 16% cheaper than Sunday options.* Opt to receive flight price alerts on the Expedia app and get notifications as soon as fares fall.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Highland?
While booking in advance is typically the easiest way to save cash, don't panic if your Highland vacation is last minute. It's still possible to find cheap flights to Highland, especially if your plans have some flexibility. Try changing your trip dates, looking at different ticket types or flying out of an alternative airport.
How far in advance should I book a flight to Highland?
Book your flight to Highland two to four months ahead if you're jetting in from an international destination. For domestic travel, the timeframe is around 28 days in advance. Lower fares and a wider variety of travel dates, schedules and seating options are some of the great reasons to book early.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Highland?
Sundays are typically the best day to book a cheap flight to Highland, with savings of about 8% on average compared to Fridays. If you purchase tickets on a Friday, expect to spend more as this is often the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Highland?
Highland has connections to 216 airports worldwide through 44 airlines, with O'Hare Intl. Airport (ORD) as its chief gateway. Pick from these leading airlines to Highland when organizing your trip:

  • United Airlines
  • American Airlines
  • Delta Air Lines
  • Alaska Airlines

Where do you fly into Highland?
The main airport when you fly to Highland is Midway Intl. Airport (MDW), but there are other nearby options like Lewis University Airport (LOT) and O'Hare Intl. Airport (ORD). You can also land at Gary, IN (GYY-Gary - Chicago Intl.) and Valparaiso, IN (VPZ-Porter County Municipal) when flying to Highland.
How far is the airport from central Highland?
If you're arriving at Midway Intl. Airport (MDW), you'll be roughly 20 mi northwest of the center of Highland.
Can I save money by booking a Highland trip package?
Book a Highland flight and hotel package deal on Expedia, and you can benefit from significant savings. It's a breeze to bundle your flight and hotel, and you can add activities and car rentals to create your own customized Highland trip. Plus, nothing beats the convenience of booking everything in one place.
Can I change or cancel my flight to Highland?
If you booked your flight to Highland in the last 24 hours, you can often change or cancel it without fees. After that, additional costs may apply depending on the airline's terms and conditions. To learn more, check out our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be issued a credit toward a future trip rather than a direct refund. When browsing on Expedia, check the "Changes included" or "No cancel fee" boxes to see fares with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

 

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Travel information

Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
$113

Trending flights to Highland

Prices were available within the past 7 days and start at $49 for one-way flights and $98 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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