$44 Cheap Flights to Winthrop Harbor, IL

Flights to Winthrop Harbor at a glance

Traveling to Winthrop Harbor is easy—simply choose between full-service and budget airlines. Compare travel times and select the flight that best fits your budget, schedule, and plans for exploring the city's renowned sights and neighborhoods.

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

Popular airport near Winthrop Harbor

Winthrop Harbor is a charming city perfect for family getaways, outdoor adventures, and scenic vacations. Visitors are drawn to its beautiful landscapes, romantic spots, and vibrant city life. It's conveniently accessible via a major airport, making travel easy for all.

• O'Hare International Airport (ORD): Situated in Cook County, Illinois, approximately 35 miles from Winthrop Harbor, this airport facilitates a wide range of travel options, covering over 285 domestic cities and more than 315 international destinations. Passengers can elevate their travel experience by opting for first class, premium economy class, or business class seating, depending on the airlines and routes available. Major airlines that operate from this busy hub include American Airlines, United, and Frontier Airlines.

Top routes to Winthrop Harbor

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

Cheapest routes to Winthrop Harbor

• Burlington (BRL/BTV) to Winthrop Harbor (ORD), with budget one-way fares from around $40
• New York (JFK/LGA) to Winthrop Harbor (ORD), with budget one-way fares from around $45
• Atlanta (ATL) to Winthrop Harbor (ORD), with cheap one-way fares from around $45
• Fort Lauderdale (FLL) to Winthrop Harbor (ORD), with cheap one-way fares from around $45
• Nashville (BNA) to Winthrop Harbor (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 Winthrop Harbor

• American Airlines: Operating flights to O'Hare International Airport (ORD), this airline represents about 36% of arrivals in Winthrop Harbor. The average one-way ticket costs around $390, with premium service options including premium economy, business, and first class depending on the route.
• United: Also flying into O'Hare International Airport (ORD), United accounts for approximately 35% of the arrivals to Winthrop Harbor. Travelers can expect an average one-way fare of about $380, with premium cabins such as premium economy, business, and first class available based on the route.
• Delta: Serving O'Hare International Airport (ORD), Delta contributes around 8% of arrivals to Winthrop Harbor. The typical one-way fare is roughly $360, with options for premium economy, business, and first class depending on the route.
• Frontier Airlines: This airline flies to O'Hare International Airport (ORD) and makes up about 3% of arrivals in Winthrop Harbor. The average one-way fare stands at approximately $160, offering a budget-friendly travel option.
• Southwest Airlines: Operating flights to O'Hare International Airport (ORD), Southwest accounts for around 2% of arrivals to Winthrop Harbor. The average one-way fare is about $230, catering to travelers seeking affordable options.

Best time to fly to Winthrop Harbor

The most popular months for travelers to fly to Winthrop Harbor are January, March, and April, when peak temperatures in Winthrop Harbor can reach up to 44.2°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 65.1°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 Winthrop Harbor

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

*For members. Select hotels.

Arriving in Winthrop Harbor

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

• Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is conveniently located about 0.1 miles away on foot, while Rosemont Station, a train station, is approximately 2.2 miles from the airport and typically accessed by car.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Winthrop Harbor, with private rides that can be arranged in advance.
• Car rental: Renting a car in Winthrop Harbor is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Winthrop Harbor 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 Winthrop Harbor

• Waukegan: Waukegan is located 8 miles drive away from Winthrop Harbor and offers a vibrant mix of family-friendly activities and outdoor experiences. This city features a variety of popular venues, including shopping centers and a theater. Notable attractions include the thrilling Six Flags Great America theme park, the scenic Waukegan Harbor, perfect for beach outings, and the Waukegan SportsPark, an arena ideal for entertainment. Whether you're looking for adventure or relaxation, Waukegan has something for everyone.
• Kenosha: Kenosha is located 7 miles drive away from Winthrop Harbor and is an excellent destination for outdoor enthusiasts and couples seeking picturesque scenery. Visitors can explore various recreational areas and engage in shopping at local centers. Key points of interest include the historic Carthage College, the lively Bristol Renaissance Faire, and the modern University of Wisconsin-Parkside. With its beautiful lakes and beaches, Kenosha is a delightful spot for a romantic getaway or a family outing.
• Beach Park: Beach Park is located 3 miles drive away from Winthrop Harbor and is a charming village known for its outdoor activities and family-friendly atmosphere. Here, travelers can enjoy campgrounds and scenic spots while exploring shopping options. Noteworthy attractions include the popular Six Flags Great America theme park, the serene Illinois Beach State Park, and the Waukegan SportsPark for various events and activities. Beach Park is perfect for those looking to unwind and enjoy nature.

Tips for short-haul flights to Winthrop Harbor

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 your space by using travel-sized toiletries, wearing your heaviest clothing, and strategically planning your outfits. This approach also allows you to bypass the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. To keep yourself engaged, download TV shows, movies, music, or podcasts beforehand, and consider bringing a book. Remember to fully charge your devices prior to boarding.
• 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 departure to accommodate for traffic and security lines.
• Bring your own snacks and water—pack your favorite snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Winthrop Harbor

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 crucial for comfort. Full-service airlines typically allow free seat selection once online check-in opens, usually 24–48 hours before your flight. Some airlines may offer this option even earlier.
• Arrive at the airport in plenty of time—make sure to arrive at the airport at least 3 hours before your 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 browse the shops, enjoy a coffee, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and readily available.
• Adjust to the new time zone mid-flight—begin acclimating your body clock by changing your watch and sleep schedule to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time of your arrival to help minimize jet lag.

Tips to find the cheapest flights to Winthrop Harbor

The cheapest day to fly

Get started finding a cheap flight to Winthrop Harbor 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 Winthrop Harbor. 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 Winthrop Harbor. 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 Winthrop Harbor, 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 Winthrop Harbor

The lowest price for round-trip flights to Winthrop Harbor in 2026 starts from $105, while one-way tickets start from from $44. 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 Winthrop Harbor. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Winthrop Harbor

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

The most affordable airports to fly into

To view the cheapest airports to fly into for Winthrop Harbor, 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 Winthrop Harbor. 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 Winthrop Harbor 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 Winthrop Harbor

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 Winthrop Harbor.

Stopover savings

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