$55 Cheap Spirit Airlines flights Chicago (ORD) to Boston (BOS)

You can discover cheap return Spirit Airlines flights from $109 from ORD to BOS by organizing your results from “Price (lowest to highest)” on Expedia. Or look for deals from $55 for a one-way journey.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines flights to Boston are usually more affordable in the low-season months of January and February. Whether you’re searching for a one-way or round-trip ticket, you could score a better deal then.

Look for affordable Spirit Airlines flights from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) one to three months prior to your departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare type and itinerary, the best day to book a domestic flight is usually Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

To see if there’s a direct route from ORD to BOS with Spirit Airlines or any other airlines, select the “Nonstop” filter when searching for flights.

Find Spirit Airlines’s earliest flights from ORD to BOS by checking our “Morning” and “Early Morning” filters. Not only will you arrive sooner, early departures also have a 20% less chance of being canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Spirit Airlines flights from O’Hare Intl. Airport (ORD) to Boston land at Logan Intl. Airport (BOS). This is the main gateway to this destination.

Offering a rewarding loyalty program, Spirit Airlines is a top choice for many passengers journeying from ORD to BOS. Plus, if you’re a Free Spirit and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

You can usually change or cancel your flight, although there may be a charge if you booked more than 24 hours ago. Need to keep your options open? Use our “No cancel fee” and “Changes included” filters to find flights that won’t penalize you if you have to alter your plans. To make changes, head to “Trips,” select your flight and click on “Manage Booking” for more details.