$38 Cheap Flights to Winnetka, IL

Flights to Winnetka at a glance

Traveling to Winnetka is easy—simply choose between full-service and budget airlines. Evaluate flight durations and select the option that best aligns with your budget, schedule, and plans for exploring the city's renowned attractions and neighborhoods.

• Major airports near Winnetka: O'Hare International Airport (ORD), Midway International Airport (MDW)
• Closest (typical) airport to Winnetka: O'Hare International Airport, ORD (around 13 miles)
• Flights per week: 9,800+ flights arriving across Winnetka airports
• Number of airlines that fly to Winnetka: around 75+ carriers

Popular airports near Winnetka

Winnetka is a charming city ideal for outdoor adventures, family getaways, and scenic vacations. Visitors are drawn to this destination for its family-friendly atmosphere, vibrant city life, outdoor activities, business opportunities, and rich culture. It is conveniently served by two major airports.

• O'Hare International Airport (ORD): Situated in Cook County, Illinois, approximately 13 miles from Winnetka, this airport facilitates both domestic and international travel. It connects to over 285 domestic cities and more than 315 international destinations. Travelers have the option to enhance their flight experience by opting for first class, premium economy, or business class seating, depending on their chosen airline and route. Major airlines operating here include American Airlines, United, and Frontier Airlines.
• Midway International Airport (MDW): Found in Cook County, Illinois, around 22 miles from Winnetka, this airport caters to both domestic and international flights, linking to over 130 domestic cities and around 30 international destinations. Passengers can choose to upgrade to premium economy or first class seating for a more comfortable journey, based on the airline and route. Well-known carriers at this airport include Southwest Airlines, Frontier Airlines, and Delta.

Top routes to Winnetka

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

Cheapest routes to Winnetka

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

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

Top airlines with flights to Winnetka

• American Airlines: Operating flights to O'Hare International Airport (ORD), American Airlines represents about 31% of arrivals to Winnetka. The average fare for a one-way ticket is around $390. Depending on the route, travelers can choose from premium economy, business class, and first class.
• United: Also servicing O'Hare International Airport (ORD), United accounts for nearly 31% of arrivals in Winnetka. The typical one-way fare is approximately $380. Premium cabin options, including premium economy, business, and first class, vary by route.
• Southwest Airlines: Flying to both O'Hare International Airport (ORD) and Midway International Airport (MDW), Southwest Airlines makes up around 12% of arrivals to Winnetka. Average one-way fares are approximately $220, offering a budget-friendly option for travelers.
• Delta: Providing service to O'Hare International Airport (ORD) and Midway International Airport (MDW), Delta represents about 8% of arrivals to Winnetka. One-way fares average around $290, with premium economy, business class, and first class available depending on the route.
• Frontier Airlines: Serving O'Hare International Airport (ORD) and Midway International Airport (MDW), Frontier Airlines accounts for about 4% of arrivals to Winnetka. The average fare for a one-way ticket is roughly $160, making it a low-cost travel choice.

Best time to fly to Winnetka

The most popular months for travelers to fly to Winnetka are January, March, and April, when peak temperatures in Winnetka can reach up to 46°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 66.7°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.

*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 Winnetka

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

*For members. Select hotels.

Arriving in Winnetka

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

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

• Chicago: As a bustling metropolis, Chicago serves as a gateway for travelers looking to experience urban life. Winnetka is situated in Chicago, providing easy access to a variety of attractions. Visitors can indulge in shopping, enjoy arena entertainment, or catch a show in one of the city’s theaters. Notable points of interest include the Griffin Museum of Science and Industry, where families can explore engaging exhibits, and 875 North Michigan Avenue, an iconic skyscraper that offers stunning city views. Don't miss a stroll down Michigan Avenue for a quintessential Chicago experience.
• Glenview: Glenview is located 4 miles away from Winnetka and is an excellent destination for families and outdoor enthusiasts. The city features a mix of educational attractions, shopping centers, and parks that cater to all ages. Visitors can explore the beautiful Chicago Botanic Garden, perfect for a romantic outing or a family day out. Additionally, Northwestern University provides a vibrant campus atmosphere, while the Donald E. Stephens Convention Center hosts a variety of events and conferences throughout the year, making it a hub for business travelers.
• Golf: Golf is located 4 miles away from Winnetka and is renowned for its outdoor and sporting activities. Ideal for families, this quaint city features scenic parks and picturesque lakes that encourage outdoor fun. Golf enthusiasts can take advantage of the local golf courses, while others might enjoy a leisurely walk in the urban parks. Highlights include Northwestern University, which adds a lively academic vibe, and Adagio Teas, a charming spot for tea lovers looking to unwind after a day of exploration.

Tips for short-haul flights to Winnetka

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 travel-sized toiletries, wearing your bulkiest clothing, and planning your outfits thoughtfully. This approach also helps you avoid the hassle of waiting at baggage claim upon arrival.
• 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. Make sure to fully charge your devices before you board.
• Arrive at the airport in plenty of time—it's advisable to arrive at least 1.5 to 2 hours prior to departure, even for short or domestic flights, taking into account potential traffic and security lines.
• Bring your own snacks and water—pack your favorite snacks and a reusable water bottle to stay hydrated while saving money at the airport.

Tips for long-haul flights to Winnetka

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

• Select your seat in advance—for long-haul flights, choosing your seat ahead of time is essential for comfort. Full-service airlines typically allow free seat selection once online check-in opens, which is generally 24–48 hours prior to your flight. Some airlines may even permit seat selection earlier than this.
• Arrive at the airport in plenty of time—make sure to arrive at the airport at least 3 hours before departure for international flights to accommodate check-in, security screening, 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. Airport Wi-Fi is usually free and readily available.
• Adjust to the new time zone mid-flight—begin synchronizing your body clock by changing your watch and sleep pattern to align with your destination's time zone. Try to either sleep or stay awake during the flight according to the local time at your arrival destination to help minimize jet lag.

Tips to find the cheapest flights to Winnetka

The cheapest day to fly

Get started finding a cheap flight to Winnetka 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 Winnetka. 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 Winnetka. 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 Winnetka, 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 Winnetka

The lowest price for round-trip flights to Winnetka in 2026 starts from $76, while one-way tickets start from from $38. 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 Winnetka. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Winnetka

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

The most affordable airports to fly into

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

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 Winnetka.

Stopover savings

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