Cheap Flights to Winthrop Harbor, IL

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Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

June is typically the cheapest month to fly

From $77 - $248 per traveler.

Graph displaying average flight prices per month

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

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 2025 starts from , while one-way tickets start from . 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

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.

Frequently asked questions

What month is the cheapest to fly to Winthrop Harbor?
Flights to Winthrop Harbor are typically the cheapest in October *. You could land a good deal for fares during this time if you keep your eyes peeled. *Cheapest month to fly is based on the month with the cheapest flight found on Expedia.com in the next 330 days.
Which US cities have the cheapest flights to Winthrop Harbor?
Get cheap flights to Winthrop Harbor from New York, Washington and Dallas. These cities generally offer the lowest fares to this much-loved destination. But bear in mind that holiday periods, stopovers and demand also influence rates, so remain flexible and book when you spot a bargain.
Which US cities fly direct to Winthrop Harbor?
There are 150 US cities that you can fly to Winthrop Harbor directly from. Compare your options by using the "Direct flights only" box on Expedia and find the best starting point for your trip. Here are some of the leading cities to leave from:

  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix

How to find a cheap flight to Winthrop Harbor?
Book well in advance or look for a cheap flight to Winthrop Harbor during the low season, such as January and February. Flying off on a Thursday can also save you 16% on average compared to a Sunday flight.* The Expedia app makes it even easier to know exactly when to book. Just turn on the toggle for "Watch prices" and you'll receive an alert when there's a better deal.*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 Winthrop Harbor?
Being flexible about your plans can help you to secure last-minute offers on cheap flights to Winthrop Harbor. To view all the available options, try looking at different ticket types, changing your Winthrop Harbor vacation dates, leaving from an alternative airport or going with another airline.
How far in advance should I book a flight to Winthrop Harbor?
Find the travel dates you want and a fare your budget will love by booking your domestic flight to Winthrop Harbor up to 28 days in advance. Lock in tickets between two and four months ahead if you're headed to Winthrop Harbor 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 Winthrop Harbor?
Sundays are generally the best day to book a cheap flight to Winthrop Harbor, where you can save 8% on average compared to Fridays. If you choose to purchase on a Friday, expect to pay more as this is typically 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 Winthrop Harbor?
A total of 44 carriers connect 216 airports across the world to Winthrop Harbor. Here are some of the major airlines to Winthrop Harbor, where O'Hare Intl. Airport (ORD) is the major gateway:

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

Where do you fly into Winthrop Harbor?
The main airport when you fly to Winthrop Harbor is General Mitchell Intl. Airport (MKE), but there are other nearby choices like O'Hare Intl. Airport (ORD) and Midway Intl. Airport (MDW). You can also land at Lewis University Airport (LOT) and Waukegan Regional Airport (UGN) when flying to Winthrop Harbor.
How far is the airport from central Winthrop Harbor?
You'll be approximately 35 mi north of the center of Winthrop Harbor after jetting into General Mitchell Intl. Airport (MKE).
Can I save money by booking a Winthrop Harbor trip package?
Book a Winthrop Harbor flight and hotel package deal on Expedia, and you could make significant savings. It's easy to bundle your flights and accommodations, and you can also add car rentals and tours to create your own customized Winthrop Harbor trip. Plus, nothing beats the convenience of booking everything in the same place.
Can I change or cancel my flight to Winthrop Harbor?
If you booked your flight to Winthrop Harbor within the last 24 hours, you can often change or cancel it for free. After that, extra charges may apply depending on the airline's terms and conditions. For more information, visit our Customer Service Portal. Keep in mind that some flights are non-refundable, so you may receive a credit for future flights rather than a direct refund. When browsing on Expedia, check the "Changes included" or "No cancel fee" filters to compare tickets with flexible change policies.
Flights to Winthrop Harbor information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$100

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*Available to One Key members.