$57 Cheap Flights from Boston (BOS) to Chicago (ORD)

View $57 flight on Wed, Aug 20, 2025Opens in a new window

Popular airlines from Logan International Airport (BOS) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Boston to Chicago (BOS-ORD)

Prices were available within the past 7 days and start at $57 for one-way flights and $116 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Aug 20 - Wed, Sep 3
BOS
Boston
ORD
Chicago
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Aug 20 from Boston to Chicago, returning Wed, Sep 3, priced at $116 found 1 day ago
Spirit Airlines
Wed, Aug 20 - Wed, Sep 3
BOS
Boston
ORD
Chicago
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Aug 20 from Boston to Chicago, returning Wed, Sep 3, priced at $116 found 1 day ago
JetBlue Airways
Tue, Sep 2 - Thu, Sep 4
BOS
Boston
ORD
Chicago
$117 Roundtrip, found 18 hours ago
$117
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Tue, Sep 2 from Boston to Chicago, returning Thu, Sep 4, priced at $117 found 18 hours ago
JetBlue Airways
Tue, Aug 19 - Wed, Aug 20
BOS
Boston
ORD
Chicago
$126 Roundtrip, found 1 hour ago
$126
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Aug 19 from Boston to Chicago, returning Wed, Aug 20, priced at $126 found 1 hour ago
JetBlue Airways
Mon, Aug 18 - Wed, Aug 20
BOS
Boston
ORD
Chicago
$126 Roundtrip, found 10 hours ago
$126
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Mon, Aug 18 from Boston to Chicago, returning Wed, Aug 20, priced at $126 found 10 hours ago
JetBlue Airways
Thu, Sep 4 - Mon, Sep 8
BOS
Boston
ORD
Chicago
$127 Roundtrip, just found
$127
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Sep 4 from Boston to Chicago, returning Mon, Sep 8, priced at $127 just found
Spirit Airlines
Tue, Aug 26 - Thu, Sep 4
BOS
Boston
ORD
Chicago
$129 Roundtrip, found 3 hours ago
$129
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Aug 26 from Boston to Chicago, returning Thu, Sep 4, priced at $129 found 3 hours ago
Southwest Airlines
Tue, Aug 19 - Wed, Aug 20
BOS
Boston
ORD
Chicago
$135 Roundtrip, found 1 hour ago
$135
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Aug 19 from Boston to Chicago, returning Wed, Aug 20, priced at $135 found 1 hour ago
American Airlines
Sun, Sep 7 - Mon, Sep 15
BOS
Boston
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select American Airlines flight, departing Sun, Sep 7 from Boston to Chicago, returning Mon, Sep 15, priced at $137 just found
Delta
Wed, Nov 12 - Tue, Dec 2
BOS
Boston
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Delta flight, departing Wed, Nov 12 from Boston to Chicago, returning Tue, Dec 2, priced at $137 just found

Find the cheapest month to fly from Boston (BOS) to Chicago (ORD)

September is typically the cheapest month to fly

From $48 - $114 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $393
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $393
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
Roundtrip price
$111
Distance
863 mi
Average flight time
1 hour 52 mins

Boston to Chicago Flights

The cheapest times to fly from Boston to Chicago

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

 

The best time to book a flight from Boston to Chicago

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

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 Boston to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $57 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 Boston to Chicago 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 Boston to Chicago 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 much does a flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD) cost?
You can pick up cheap return flights starting from $117 from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a JetBlue Airways flight leaving BOS on July 29 2025 and touching down at ORD. The price was last updated on July 17 2025 and has not changed since.
What is the cheapest month to fly from BOS to ORD?
The cheapest flights from BOS to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Take the express route to O'Hare Intl. Airport (ORD). 4 carriers offer nonstop flights from Logan Intl. Airport (BOS), including:

  • American Airlines
  • United Airlines
  • Delta Air Lines

What is the cheapest airline that flies from BOS to ORD?
With fares starting at $58 for a one-way journey from BOS to ORD, JetBlue Airways is currently the cheapest airline flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from BOS on September 4 2025. Prices were last updated on July 17 2025 and have not changed since.
How many flights per day from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
When departing from Logan Intl. Airport (BOS), you'll have your pick from an average of 16 daily direct flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Flights between BOS and ORD tend to be busiest at 6 AM. If you want a quieter experience and possibly cheaper prices, look for a time when demand is lower.
What day of the week has the most flights from BOS to ORD?
Depart on a Friday if you're searching for the best choice of flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
The first flight of the day leaving from Logan Intl. Airport (BOS) is at around 6:00AM UTC-5. Board this flight and you'll touch down at O'Hare Intl. Airport (ORD) at approximately 8:08AM UTC-6. The overall travel time is 3h 8m.
How long does it take to fly from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
The average flight duration from BOS to ORD is 3 hours and 2 minutes, covering a total distance of 860 mi.
What airline has the least delays from BOS to ORD?
With 100% of flights usually arriving as scheduled, Alaska Airlines has the best on-time performance for nonstop flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD). To check your flight status and receive notifications if anything changes, use the Expedia App.
What is the best time to fly from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Select a flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the likelihood of delays. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Logan Intl. Airport (BOS)?
Catch a direct flight from Logan Intl. Airport (BOS) to Chicago and land at O'Hare Intl. Airport (ORD). Another convenient point of entry into the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from BOS to ORD shortly before your journey is usually more expensive. However, if there's some wiggle room with your travel dates and times, you could grab a cheap last-minute fare.
Is it cheaper to book a BOS to ORD flight and hotel package?
Booking a BOS to ORD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Choose from our wide range of hotels and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Generally, it's possible to reschedule or cancel your BOS to ORD flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

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