$21 Cheap Flights from Chicago (ORD) to Boston (BOS)

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Cheap Flights from Chicago to Boston (ORD-BOS)

Prices were available within the past 7 days and start at $21 for one-way flights and $47 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Jun 5 - Wed, Jun 12
ORD
Chicago
BOS
Boston
$47 Roundtrip, found 7 hours ago
$47
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, Jun 5 from Chicago to Boston, returning Wed, Jun 12, priced at $47 found 7 hours ago
Spirit Airlines
Wed, Jun 5 - Sat, Jun 8
ORD
Chicago
BOS
Boston
$52 Roundtrip, just found
$52
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jun 5 from Chicago to Boston, returning Sat, Jun 8, priced at $52 just found
Spirit Airlines
Sat, Jun 8 - Wed, Jun 12
ORD
Chicago
BOS
Boston
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jun 8 from Chicago to Boston, returning Wed, Jun 12, priced at $58 just found
Spirit Airlines
Sat, Jun 8 - Tue, Jun 11
ORD
Chicago
BOS
Boston
$63 Roundtrip, found 2 hours ago
$63
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Jun 8 from Chicago to Boston, returning Tue, Jun 11, priced at $63 found 2 hours ago
Spirit Airlines
Wed, Jun 5 - Wed, Jun 12
ORD
Chicago
BOS
Boston
$67 Roundtrip, found 7 hours ago
$67
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, Jun 5 from Chicago to Boston, returning Wed, Jun 12, priced at $67 found 7 hours ago
Spirit Airlines
Fri, Jun 7 - Wed, Jun 12
ORD
Chicago
BOS
Boston
$70 Roundtrip, found 5 hours ago
$70
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Fri, Jun 7 from Chicago to Boston, returning Wed, Jun 12, priced at $70 found 5 hours ago
Spirit Airlines
Wed, Jun 5 - Sat, Jun 8
ORD
Chicago
BOS
Boston
$72 Roundtrip, just found
$72
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jun 5 from Chicago to Boston, returning Sat, Jun 8, priced at $72 just found
Spirit Airlines
Tue, Jun 11 - Wed, Jun 12
ORD
Chicago
BOS
Boston
$73 Roundtrip, found 6 hours ago
$73
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Jun 11 from Chicago to Boston, returning Wed, Jun 12, priced at $73 found 6 hours ago
Spirit Airlines
Fri, Jun 7 - Tue, Jun 11
ORD
Chicago
BOS
Boston
$75 Roundtrip, just found
$75
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jun 7 from Chicago to Boston, returning Tue, Jun 11, priced at $75 just found
Spirit Airlines
Sat, Jun 8 - Wed, Jun 12
ORD
Chicago
BOS
Boston
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jun 8 from Chicago to Boston, returning Wed, Jun 12, priced at $78 just found
Flights from Chicago (ORD) to Boston (BOS)
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$46
Distance
863 mi

Chicago to Boston Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Boston offer the perfect respite. Not only does exploring Boston provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Boston may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from ORD to BOS today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Boston are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Boston more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Boston is $21 now!

Frequently asked questions

How much is a one-way flight from O'Hare Airport to Logan Intl. Airport (BOS)?
You can get one-way Chicago flights to Boston starting from $32. This information is based on the lowest price located on Expedia for this journey leaving during the next three months and was last updated on May 3 2024 and has not changed since. This fare is for an Spirit Airlines service, jetting off from O’Hare Intl. Airport (ORD) on June 18 2024 and landing at Logan Intl. Airport.
How long does it take to fly from O'Hare Airport to BOS?
A direct flight with American Airlines takes around 2 hours and 17 minutes. Step on board the 1:25PM flight from O’Hare Airport and come in to land at Logan Intl. Airport at 4:42PM. Snap up a superb deal on this and other routes when you book your fare with Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Logan Intl. Airport last minute?
When it’s time to book your flights, it pays to be prepared. While you may be able to score a deal on an O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) flight at the last minute, prices usually don’t get cheaper as the date of departure 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 in advance. For international trips it’s three to four months.
What is the cheapest airline flying from O'Hare Intl. Airport (ORD) to BOS in the next 90 days?
The cheapest airline flying from Chicago to Boston found on Expedia is Spirit Airlines, with fares starting at $32. This price is based on fares found on Expedia with a departure date within the next 90 days. The flight departs ORD on June 18 2024 and arrives at Logan Intl. Airport (BOS). Pricing information was updated on May 3 2024 and has not changed since.
What's the cheapest price for a flight from O'Hare Intl. Airport (ORD) to BOS next month?
The cheapest ticket for a one-way flight from Chicago to Boston over the next month is $52. If you’re looking to travel soon, now’s the time to lock in this fare. This price was found after searching all available flights on Expedia departing within the next 30 days. This airfare is for a one-way Spirit Airlines flight taking off from O’Hare Airport on May 30 2024 and getting into Logan Intl. Airport (BOS). Pricing info was updated on May 3 2024 and has not changed since.
What airline has the least delays from ORD to BOS?
With an on-time arrival rate of 85%, United Airlines is the airline that’s most likely to get you from O’Hare Intl. Airport (ORD) to Logan Intl. Airport without any holdups. Flight delays can be a nice excuse to relax in the airport lounge. However, they can also lead to a missed connection or even ruin your entire trip. Stay updated about delays by looking up your flight status through the free Expedia App before you set off for the airport. If you’re already at your gate and the delay will significantly impact your plans, head to your airline’s customer service desk to find out what your options are.
Can I find cheap nonstop flights from O'Hare Airport to BOS in the next three months?
The next trip you take doesn’t need to break the bank. We’ve located a roundtrip nonstop flight from Chicago to Boston within the next 90 days for $63. This price is based on fares found on Expedia with a departure date within the next three months and was last updated on May 3 2024. The flight via Spirit Airlines heads out of O’Hare Intl. Airport (ORD) on May 29 2024 and lands at Logan Intl. Airport (BOS). It has a return date of June 6 2024.Make use of our filters to search for nonstop cheap flights from O’Hare Airport to BOS. Simply click on “Nonstop” under “Filter by” once your search results appear. Travel plans not etched in stone? You can also make use of the “Flexible dates” dropdown menu to compare prices for nearby days. Booking a fare that best fits your budget and timetable couldn’t be simpler.
What airports do you fly into for Boston from Chicago?
Logan Intl. Airport (BOS), Manchester-Boston Regional Airport (MHT) and Provincetown Municipal Airport (PVC) are your options when heading off from Chicago to Boston. Approximately 2 mi east of the center of Boston, Logan Intl. Airport (BOS) is the city’s major gateway. Consider factors like flight schedules and the distance to your hotel before deciding where you fly into. Fenway Park and Boston Common are two amazing attractions to put on your must-see list when you arrive at your destination.
What are the most popular departure times for flights from ORD to BOS?
For American Airlines flights jetting from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS), the most popular period is between 6:00 AM - 7:00 AM. If you want to avoid those frustrating delays, book the earliest flight. This way you can dodge the heavy air traffic that accumulates in the afternoon and evening.
Can I change the date of my flight from O'Hare Intl. Airport (ORD) to BOS?
It’s a breeze to make amendments to your O’Hare Airport to Logan Intl. Airport (BOS) journey yourself. Just log in to the Expedia Trips portal and hit “change flight.” Look for new flights and secure the one that works best. You’ll see an estimate of your flight change cost, if applicable. You can also find your way to our Customer Service portal to chat to our Virtual Agent and get answers to all your questions.
Boston nearby Airports

Manchester

Chicago to Manchester-Boston Regional
$168.21

Worcester

Chicago to Worcester Regional
$192.71

Providence

Chicago to T.F. Green
$236.19

Provincetown

Chicago to Provincetown Municipal
$513.91

New Bedford

Chicago to New Bedford Regional
$839.70
Chicago nearby Airports

Chicago

Midway Intl. to Boston
$107.94
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