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$30 Cheap Flights to Hillside, IL

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Popular airlines to Hillside

Today's featured flight deals to Hillside

NonstopCarry-on includedLower price than typical

How much is the cheapest flight to Hillside?

Prices were available within the past 7 days and start at $30 for one-way flights and $60 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
American Airlines
United
Southwest Airlines
Delta

Alternative airports near Hillside

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

What you need to know for your flight to Hillside

Flights to Hillside at a glance

Traveling to Hillside is easy; select from both full-service and budget airlines. Compare flight durations and choose the option that best fits your budget and schedule, all while planning to visit the city’s renowned attractions and neighborhoods.

  • Major airports near Hillside: O'Hare International Airport (ORD), Midway International Airport (MDW)
  • Closest airport to Hillside: O'Hare International Airport, ORD (around 7 miles)
  • Flights per week: 9,800+ flights arriving across Hillside airports
  • Number of airlines that fly to Hillside: around 75+ carriers

Popular airports near Hillside

Hillside is a vibrant city that caters to families and those seeking outdoor adventures, city experiences, or business opportunities. Travelers are drawn to Hillside for its diverse entertainment options, and it is accessible via two major airports.

  • O'Hare International Airport (ORD): Situated in Cook County, Illinois, approximately 7 miles from Hillside, this major airport accommodates both domestic and international flights, linking travelers to over 285 domestic cities and more than 315 international locations. Passengers have the option to enhance their travel experience by upgrading to first class, premium economy, or business class seating, depending on their chosen airlines and routes. Key airlines operating at this airport include American Airlines, United, and Frontier Airlines.
  • Midway International Airport (MDW): Found in Cook County, Illinois, about 10 miles from Hillside, this airport offers connectivity to roughly 130 domestic cities and around 30 international destinations for both domestic and international travelers. Passengers can opt for upgrades to premium economy or first class service, based on the airlines and routes they select. Notable carriers serving this airport include Southwest Airlines, Frontier Airlines, and Delta.

Top routes to Hillside

  • New York (JFK/LGA) to Hillside (ORD/MDW), with one-way airfare from around $45
  • Los Angeles (LAX) to Hillside (ORD/MDW), with one-way flights starting at around $80
  • Boston (BOS) to Hillside (ORD/MDW), with one-way fares starting at around $50
  • Orlando (MCO) to Hillside (ORD/MDW), with one-way flights starting at around $45
  • Atlanta (ATL) to Hillside (ORD/MDW), with one-way flight options from around $40

Cheapest routes to Hillside

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

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

Top airlines with flights to Hillside

  • American Airlines: Operating flights to O'Hare International Airport (ORD), American Airlines represents about 31% of arrivals in Hillside. The average fare for a one-way ticket is around $390, with premium cabin services including premium economy, business, and first class depending on the route.
  • United: Also serving O'Hare International Airport (ORD), United accounts for roughly 31% of arrivals to Hillside. Passengers can expect an average one-way fare of about $380, with options for premium economy, business, and first class available based on the route.
  • Southwest Airlines: With flights to both O'Hare International Airport (ORD) and Midway International Airport (MDW), Southwest Airlines is responsible for approximately 12% of arrivals to Hillside. The average fare for a one-way ticket is around $220, making it a competitive option.
  • Delta: Providing service to O'Hare International Airport (ORD) and Midway International Airport (MDW), Delta makes up about 8% of Hillside arrivals. The average one-way fare is approximately $290, featuring premium cabin options like premium economy, business, and first class depending on the route.
  • Frontier Airlines: Flying to both O'Hare International Airport (ORD) and Midway International Airport (MDW), Frontier Airlines accounts for around 4% of arrivals to Hillside. One-way fares are generally around $160, positioning it as an economical choice for travelers.

Best time to fly to Hillside

The most popular months for travelers to fly to Hillside are January, March, and April, when peak temperatures in Hillside can reach up to 47.8°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 67.3°F and typically the lowest average one-way fare (around $200), 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 $201 to $214, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January24.3°F (-4.3°C)Light RainMostly CloudyModerately High$275
February26.2°F (-3.2°C)Light RainMostly CloudyAverage$217
March38.3°F (3.5°C)Light RainMostly CloudyModerately High$242
April47.8°F (8.8°C)Light RainMostly CloudyModerately High$232
May59.7°F (15.4°C)Light RainMostly SunnyAverage$214
June69.8°F (21.0°C)Light RainMostly SunnyAverage$226
July74.5°F (23.6°C)Light RainMostly SunnyAverage$223
August73.6°F (23.1°C)Light RainMostly SunnyAverage$215
September67.3°F (19.6°C)Light RainMostly SunnyModerately Low$200
October54.5°F (12.5°C)Light RainMostly SunnyAverage$201
November41.4°F (5.2°C)Light RainMostly SunnyModerately Low$212
December31.8°F (-0.1°C)Light RainMostly CloudyModerately Low$218

*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 Hillside

Getting some of the best deals on flights to Hillside 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 Hillside 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 Hillside flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Hillside

Hillside welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Hillside 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 typically reached by car.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Hillside, with options including free hotel shuttles and private rides, which can be arranged in advance.
  • Car rental: Renting a car in Hillside is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Hillside 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 Hillside

  • Chicago: Chicago is a bustling metropolis that offers a vibrant mix of family-friendly activities, outdoor adventures, and urban experiences. As Hillside is situated in Chicago, visitors can easily access a variety of attractions, including shopping areas, theater performances, and an array of entertainment venues. Notable highlights include the Griffin Museum of Science and Industry—a perfect stop for families—and the iconic 875 North Michigan Avenue, a stunning skyscraper that embodies the city’s architectural marvels. Whether you’re exploring urban parks or attending events at local sports facilities, Chicago has something for everyone.
  • Elmhurst: Located 2 miles drive away from Hillside, Elmhurst is a charming city that welcomes travelers seeking family fun, outdoor relaxation, and city exploration. The area boasts several shopping centers and educational institutions, making it ideal for both leisure and learning. Visitors can enjoy the Donald E. Stephens Convention Center for various events, or explore the historic Elmhurst College, which adds a cultural touch to the city. Elmhurst's parks and recreational facilities provide ample opportunities for outdoor activities, making it a delightful spot for families and nature lovers alike.
  • Maywood: Maywood is located 3 miles drive away from Hillside and is a vibrant city known for its family-oriented atmosphere and outdoor experiences. Travelers can engage in educational pursuits and enjoy entertainment at arena facilities. Maywood features the Donald E. Stephens Convention Center, perfect for business travelers, and the iconic Willis Tower, which offers breathtaking views of the city. Additionally, the Frank Lloyd Wright Historic District showcases stunning architecture, providing a rich cultural experience amidst urban parks and recreational venues. Maywood is a great destination for those looking to explore both city life and nature.

Tips for short-haul flights to Hillside

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

  • Pack light and skip checked bags—when traveling with budget airlines, it’s often more economical to go with just a carry-on. Save space by bringing travel-sized toiletries, wearing your heaviest clothing, and coordinating outfits effectively. This approach also helps you avoid the wait at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. Download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself entertained. 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 prior to 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 Hillside

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 you to select your seat for free once online check-in opens, typically 24–48 hours before your flight. Some airlines provide the option to select seats even earlier than that.
  • Arrive at the airport in plenty of time—aim to reach the airport at least 3 hours before departure for international flights to account for check-in, security, and immigration procedures.
  • Relax at the airport—if you have some extra time, explore the shops, grab a coffee, or unwind at the gate or a departure lounge if you have access. Airport Wi-Fi is generally free and available.
  • Adjust to the new time zone mid-flight—begin acclimating your body clock by setting 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 destination to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Hillside?
The cheapest month to fly to Hillside is September when demand is low. Off-peak months are often when you'll find cheap flights. To save money, avoid flying during public holidays and school breaks.
Which US cities have the cheapest flights to Hillside?
Typically, you'll find that New York, Washington and Dallas have cheap flights to Hillside. Flexibility, however, is always key to scoring yourself the best fares. Plan your trip midweek or during the off-peak season to keep costs down.
Which US cities fly direct to Hillside?
Take your pick of 150 US destinations offering direct flights to Hillside. When reserving on Expedia, click on "Direct flights only" to find nonstop itineraries. Fly to Hillside from any of these leading cities:
  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix
How to find a cheap flight to Hillside?
Book in advance or search for cheap flights to Hillside during off-season months like December and January. Leaving on a Thursday can also save you 16% on average compared to a Sunday departure.* The Expedia app makes it even easier to know exactly when to book. Just activate the toggle for "Watch prices" and get notified as soon as fares change.*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 Hillside?
It's possible to get cheap deals on last-minute departures to Hillside, especially if your travel arrangements aren't set in stone. Think about jetting out of a different airport, tweaking your trip dates or choosing another airline to get a cheap flight to Hillside.
How far in advance should I book a flight to Hillside?
Find the departure dates you want and a price that suits your budget by booking your domestic flight to Hillside up to 28 days in advance. Lock in tickets between two and four months ahead if you're flying to Hillside from an international destination.**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 Hillside?
You'll save an average of 8% if you purchase tickets on a Sunday instead of Fridays, which tend to be the most expensive day to book.* When it comes to getting a cheap flight to Hillside, timing makes a difference.*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 Hillside?
A total of 44 carriers connect 216 airports across the world to Hillside. Here are some of the most popular airlines to Hillside, where O'Hare Intl. Airport (ORD) is the major entry point:
  • United Airlines
  • American Airlines
  • Delta Air Lines
  • Alaska Airlines
Where do you fly into Hillside?
The main airport when you fly to Hillside is O'Hare Intl. Airport (ORD), but there are other nearby options like Midway Intl. Airport (MDW) and Lewis University Airport (LOT). You can also arrive at Chicago Executive Airport (PWK) and Dupage Airport (DPA) when flying to Hillside.
How far is the airport from central Hillside?
If you're flying into O'Hare Intl. Airport (ORD), you'll be about 7 mi north of the center of Hillside.
Can I save money by booking a Hillside trip package?
It's possible to save hundreds of dollars if you secure a Hillside flight and hotel package deal on Expedia. And you'll save time and hassle by having all your travel arrangements in one place. Try bundling hotels and flights with extras such as activities and car rentals for your own customized Hillside vacation.
Can I change or cancel my flight to Hillside?
It's usually possible to cancel or change your flight to Hillside. Many airlines allow you to cancel your flights for free within 24 hours of making your booking. However, some flights are non-refundable, and airlines may issue you credit for a future trip rather than a direct refund. To reserve affordable flights to Hillside with flexible change policies, select "No cancel fee" or "Changes included" during your search. Looking for more information? Head to our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

Book with confidence

Tips to find the cheapest flights to Hillside

The cheapest day to fly

Get started finding a cheap flight to Hillside 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

September is the cheapest month to fly to Hillside. 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 Hillside. 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 Hillside, 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 Hillside

The lowest price for round-trip flights to Hillside in 2026 starts from from $60, while one-way tickets start from from $30. 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 Hillside. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Hillside

Frontier Airlines, American Airlines, United, Southwest Airlines, Delta are just some of the airlines that can typically offer cheap tickets to Hillside. 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 Hillside and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Hillside, 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 Hillside. 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 Hillside 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 Hillside

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 Hillside.

Stopover savings

The cheapest tickets to Hillside are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Hillside. 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 Hillside 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 Hillside. Simply download the free Expedia app to your smart device and activate Hillside 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 Hillside. 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.

Tips to find the cheapest flights to Hillside

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$60

Trending flights to Hillside

Prices were available within the past 7 days and start at $30 for one-way flights and $60 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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