$57 Cheap Spirit Airlines flights Boston (BOS) to Chicago (ORD)

View $57 flight on Wed, Aug 6, 2025Opens in a new window

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$57 Cheap Spirit Airlines flights Boston (BOS) to Chicago (ORD)

Prices were available within the past 7 days and start at $57 for one-way flights and $114 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Jul 30 - Tue, Aug 5
BOS
Boston
ORD
Chicago
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jul 30 from Boston to Chicago, returning Tue, Aug 5, priced at $114 just found
Flights from Boston (BOS) to Chicago (ORD)
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Popular airline
JetBlue Airways
Distance
863 mi
Average flight time
1 hour 52 mins

Frequently asked questions

How much is a Spirit Airlines flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
You can find affordable round-trip Spirit Airlines flights from $114 from BOS to ORD by organizing your results from "Price (lowest to highest)" on Expedia. Or search for deals from $57 for a one-way trip.**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.
What is the cheapest month to fly from BOS to ORD with Spirit Airlines?
Search for round-trip or one-way flights to Chicago in January or February. You could find a cheap fare with Spirit Airlines during these quieter months.
What is the cheapest time to book flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD) with Spirit Airlines?
For cheap Spirit Airlines fares from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Securing domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also affect the price you pay. Sunday is typically the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your journey on a Sunday.**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.
Does Spirit Airlines fly nonstop from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Enter your dates, click search and select the "Nonstop" filter on Expedia to browse any direct flights from BOS to ORD with Spirit Airlines or another airline.
What is the earliest Spirit Airlines flight from BOS to ORD?
Find Spirit Airlines's earliest flights from BOS to ORD by selecting our "Morning" and "Early Morning" filters. Not only will you get to your destination sooner, early departures also experience 20% fewer cancellations.**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.
What airports does Spirit Airlines fly into in Chicago?
Spirit Airlines flights from Logan Intl. Airport (BOS) to Chicago come in to O'Hare Intl. Airport (ORD). This is the main gateway to this city.
Why fly with Spirit Airlines from BOS to ORD?
A rewarding loyalty program and the chance to rack up points through Free Spirit are the start of the reasons to jet off from BOS to ORD with Spirit Airlines. Plus, when you join our One Key™ program, you can receive OneKeyCash™* alongside Spirit Airlines's loyalty program earnings. It's yours to spend on future bookings.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Spirit Airlines flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Depending on your ticket type, a fee typically applies if you cancel or change your booking more than 24 hours after it's been confirmed. To secure flexible fares, select our "No cancel fee" or "Changes included" filter when looking for flights. For additional information on changing or canceling your reservation, go to "Trips," select your flight and click on "Manage Booking."

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*Available to One Key members.