$47 Cheap Flights from Chicago (ORD) to Boston (BOS)

View $47 flight on Tue, Apr 15, 2025Opens in a new window

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Cheap Flights from Chicago to Boston (ORD-BOS)

Prices were available within the past 7 days and start at $47 for one-way flights and $96 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Apr 8 - Wed, Apr 16
ORD
Chicago
BOS
Boston
$96 Roundtrip, found 4 hours ago
$96
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Apr 8 from Chicago to Boston, returning Wed, Apr 16, priced at $96 found 4 hours ago
Spirit Airlines
Tue, Apr 8 - Thu, Apr 10
ORD
Chicago
BOS
Boston
$96 Roundtrip, found 2 hours ago
$96
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Apr 8 from Chicago to Boston, returning Thu, Apr 10, priced at $96 found 2 hours ago
JetBlue Airways
Wed, Apr 16 - Wed, Apr 30
ORD
Chicago
BOS
Boston
$97 Roundtrip, just found
$97
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Apr 16 from Chicago to Boston, returning Wed, Apr 30, priced at $97 just found
Spirit Airlines
Tue, Apr 8 - Tue, Apr 15
ORD
Chicago
BOS
Boston
$107 Roundtrip, found 3 hours ago
$107
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Apr 8 from Chicago to Boston, returning Tue, Apr 15, priced at $107 found 3 hours ago
JetBlue Airways
Wed, May 14 - Tue, May 20
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 3 hours ago
$109
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Wed, May 14 from Chicago to Boston, returning Tue, May 20, priced at $109 found 3 hours ago
Spirit Airlines
Wed, May 7 - Mon, May 12
ORD
Chicago
BOS
Boston
$110 Roundtrip, found 2 hours ago
$110
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, May 7 from Chicago to Boston, returning Mon, May 12, priced at $110 found 2 hours ago
Spirit Airlines
Tue, Apr 8 - Wed, Apr 9
ORD
Chicago
BOS
Boston
$119 Roundtrip, just found
$119
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Apr 8 from Chicago to Boston, returning Wed, Apr 9, priced at $119 just found
United
Fri, May 9 - Mon, May 12
ORD
Chicago
BOS
Boston
$134 Roundtrip, just found
$134
Roundtrip
just found
Select United flight, departing Fri, May 9 from Chicago to Boston, returning Mon, May 12, priced at $134 just found
American Airlines
Wed, May 14 - Tue, May 20
ORD
Chicago
BOS
Boston
$142 Roundtrip, found 3 hours ago
$142
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, May 14 from Chicago to Boston, returning Tue, May 20, priced at $142 found 3 hours ago
Frontier Airlines
Tue, Apr 8 - Wed, Apr 9
ORD
Chicago
BOS
Boston
$174 Roundtrip, just found
$174
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Apr 8 from Chicago to Boston, returning Wed, Apr 9, priced at $174 just found
Flights from Chicago (ORD) to Boston (BOS)
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$91
Distance
863 mi
Average flight time
3 hours 17 mins

Chicago to Boston Flights

The cheapest times to fly from Chicago to Boston

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 Boston are during the month of April. You can find some of the cheapest flights from Chicago to Boston with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Boston

Sunday is one of the best days to book for cheap flights from Chicago to Boston: 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 Boston

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 Boston in 2025. You can also book with separate airlines for your outbound and return journeys, from $47 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 Boston 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 Boston 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

How long does it take to fly from O'Hare Intl. Airport (ORD) to BOS?
A direct flight with United Airlines takes approximately 2 hours and 21 minutes. Take the 9:45PM flight from ORD and arrive at Logan Intl. Airport at 1:06AM. Pick up a superb deal on this and many other routes when you use Expedia to book your trip.
Is it cheaper to buy a plane ticket from O'Hare Airport to Logan Intl. Airport last minute?
Booking your flight from ORD to BOS at the last minute could save you money if you’re lucky enough to find a real steal. However, tickets don’t usually get cheaper closer to the departure date. If you wait, flights could also be sold out or the best seats taken. If you’d rather not hedge your bets, book well ahead of the date you want to leave. In fact, Expedia has some of the biggest deals up to 12 months in advance. If your preferred airline hasn’t released its airfares yet, check back regularly as deals are updated on Expedia all the time.
What airline has the least delays from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
If you don’t want to be stuck in the departure lounge — or worse, have your trip upended because of a flight delay — take off with United Airlines. Around 85% of its O’Hare Intl. Airport (ORD) to Logan Intl. Airport services touch down on time. You can check your flight status before heading to the airport through the free Expedia App. It’ll also provide you with real-time alerts about things like gate changes, luggage carousel numbers and directions to your hotel. Everything you need to know is in your pocket with this handy travel companion.
What airports do you fly into for Boston from Chicago?
With Logan Intl. Airport (BOS), Manchester-Boston Regional Airport (MHT) and Provincetown Municipal Airport (PVC) to choose from, traveling from Chicago to Boston is simple. The city’s busiest terminal, Logan Intl. Airport (BOS), is about 2 mi east of the center. Along with the price of fares, consider factors like train or bus options from the airport and the distance to your hotel when deciding where to land. Get your Boston trip off to an awesome start by exploring Fenway Park and Boston Common.
What are the most popular departure times for flights from ORD to Logan Intl. Airport (BOS)?
For United Airlines flights jetting from O’Hare Airport to Logan Intl. Airport (BOS), the peak period is between 10:00 AM - 11:00 AM. If you want to avoid any delays, fly in the morning. This way you’re likely to avoid air traffic that builds up in the afternoon and evening.
Can I change the date of my flight from O'Hare Airport to Logan Intl. Airport (BOS)?
It’s so easy to make changes to your O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) trip yourself. Simply log in to the Expedia Trips portal and click on “change flight.” Look around for new flights and choose the one that works best. You’ll see an estimate of your flight change fee, if applicable. You can also visit our Customer Service portal to chat to our Virtual Agent and quickly get answers to all your questions.
*Available to One Key members.