Cheap Flights from Chicago (ORD) to Sheboygan (SBM)

Featured airlines

American Airlines
United
Southwest Airlines
Delta
Spirit Airlines
JetBlue Airways
Frontier Airlines
Air India
Hawaiian Airlines

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.
Flights from Chicago (ORD) to Sheboygan (SBM)
Origin airport
O'Hare Intl.
Destination airport
Sheboygan County Memorial
Distance
123 mi

Chicago to Sheboygan Flights

The cheapest times to fly from Chicago to Sheboygan

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Sheboygan are during the month of . You can find some of the cheapest flights from Chicago to Sheboygan with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Sheboygan

Sunday is one of the best days to book for cheap flights from Chicago to Sheboygan: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Sheboygan

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Sheboygan in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Sheboygan flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Sheboygan airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

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

Is it cheaper to buy a plane ticket from ORD to SBM last minute?
When it comes to booking your flights, it pays to be prepared. While it’s possible to find a deal on an O’Hare Airport to SBM flight at the last minute, fares usually don’t get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days ahead. For international travel it’s between three and four months.
What airports do you fly into for Sheboygan Falls from Chicago?
Sheboygan, WI (SBM-Sheboygan County Memorial), Appleton Intl. Airport (ATW) and Austin Straubel Intl. Airport (GRB) are your options when taking off from Chicago to Sheboygan Falls. Roughly 3 mi northwest of the center of Sheboygan Falls, Sheboygan, WI (SBM-Sheboygan County Memorial) is the city’s major hub. Think about factors like flight arrival and departure times and the distance to your hotel before deciding on an airport. Blue Harbor Resort & Conference Center Water Park and Blackwolf Run are two leading attractions to put on your to-do list when you get to your destination.
Can I change the date of my flight from O'Hare Intl. Airport (ORD) to SBM?
Expedia makes it easy to make amendments to your O’Hare Airport to SBM journey yourself. Simply log in to the Expedia Trips portal and choose “change flight.” Look for new flights and secure the one that better fits your plans. You’ll see an estimate of applicable flight change costs. You can also head to our Customer Service portal to chat to our Virtual Agent and quickly get answers to your questions.

Explore a world of travel with Expedia

*Available to One Key members.