Cheap Flights from Boston (BOS) to Chicago (ORD) from AU$103

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

Prices were available within the past 7 days and start at AU$103 for one-way flights and AU$207 for round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue., 13 Aug. - Tue., 20 Aug.
BOS
Boston
ORD
Chicago
AU$207 Return, found 1 day ago
AU$207
Return
found 1 day ago
Select American Airlines flight, departing Tue., 13 Aug. from Boston to Chicago, returning Tue., 20 Aug., priced at AU$207 found 1 day ago
American Airlines
Tue., 20 Aug. - Sat., 31 Aug.
BOS
Boston
ORD
Chicago
AU$238 Return, found 6 days ago
AU$238
Return
found 6 days ago
Select American Airlines flight, departing Tue., 20 Aug. from Boston to Chicago, returning Sat., 31 Aug., priced at AU$238 found 6 days ago
American Airlines
Tue., 13 Aug. - Tue., 20 Aug.
BOS
Boston
ORD
Chicago
AU$240 Return, found 1 day ago
AU$240
Return
found 1 day ago
Select American Airlines flight, departing Tue., 13 Aug. from Boston to Chicago, returning Tue., 20 Aug., priced at AU$240 found 1 day ago
American Airlines
Tue., 11 Jun. - Tue., 18 Jun.
BOS
Boston
ORD
Chicago
AU$240 Return, found 1 day ago
AU$240
Return
found 1 day ago
Select American Airlines flight, departing Tue., 11 Jun. from Boston to Chicago, returning Tue., 18 Jun., priced at AU$240 found 1 day ago
American Airlines
Thu., 6 Jun. - Tue., 11 Jun.
BOS
Boston
ORD
Chicago
AU$247 Return, found 3 days ago
AU$247
Return
found 3 days ago
Select American Airlines flight, departing Thu., 6 Jun. from Boston to Chicago, returning Tue., 11 Jun., priced at AU$247 found 3 days ago
American Airlines
Sat., 17 Aug. - Sat., 24 Aug.
BOS
Boston
ORD
Chicago
AU$255 Return, found 5 days ago
AU$255
Return
found 5 days ago
Select American Airlines flight, departing Sat., 17 Aug. from Boston to Chicago, returning Sat., 24 Aug., priced at AU$255 found 5 days ago
United
Tue., 11 Jun. - Tue., 18 Jun.
BOS
Boston
ORD
Chicago
AU$260 Return, found 1 day ago
AU$260
Return
found 1 day ago
Select United flight, departing Tue., 11 Jun. from Boston to Chicago, returning Tue., 18 Jun., priced at AU$260 found 1 day ago
American Airlines
Tue., 20 Aug. - Sat., 31 Aug.
BOS
Boston
ORD
Chicago
AU$269 Return, found 6 days ago
AU$269
Return
found 6 days ago
Select American Airlines flight, departing Tue., 20 Aug. from Boston to Chicago, returning Sat., 31 Aug., priced at AU$269 found 6 days ago
Delta
Tue., 24 Sep. - Wed., 25 Sep.
BOS
Boston
ORD
Chicago
AU$271 Return, found 13 hours ago
AU$271
Return
found 13 hours ago
Select Delta flight, departing Tue., 24 Sep. from Boston to Chicago, returning Wed., 25 Sep., priced at AU$271 found 13 hours ago
American Airlines
Tue., 24 Sep. - Wed., 25 Sep.
BOS
Boston
ORD
Chicago
AU$272 Return, found 13 hours ago
AU$272
Return
found 13 hours ago
Select American Airlines flight, departing Tue., 24 Sep. from Boston to Chicago, returning Wed., 25 Sep., priced at AU$272 found 13 hours ago
Flight from Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
AU$207
Distance
1381 km
Average flight time
1 hour 48 mins

Your quick guide to flights from Boston to Chicago

Pick up great flights from Boston to Chicago

With Expedia, you have your pick of 68 flights a day with 20 airlines covering flights from Boston to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Boston to Chicago that take around 0 hours.

Find cheap flights from Boston to Chicago

From the great flight deals with prices currently ranging from AU$207 to AU$272, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Boston to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in August.

Reasons to book your flight from Boston to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Boston to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Frequently asked questions

How much is a flight from Logan Intl. Airport to ORD?
If you’re planning on travelling from BOS to O’Hare Airport, round-trip flights start from AU$207. This price is based on airfares advertised within the last 7 days on Expedia for flights departing within the next year, so don’t hang about. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport (BOS) to ORD?
The majority of flights can be conveniently cancelled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from BOS to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Logan Intl. Airport to O’Hare Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from BOS to O'Hare Intl. Airport (ORD)?
Forget about a movie marathon on this flight — it’s only 1 400 kilometres from Boston to Chicago. Sit down, buckle up and you’ll be touching down before long.
Which airlines fly direct from Logan Intl. Airport to ORD?
It’s a breeze to fly directly from Logan Intl. Airport to ORD. Below are some of the top carriers that operate nonstop services on this route:

  • American Airlines - (AA) with 230 monthly flights
  • United Airlines - (UA) with 178 monthly flights
  • Delta Air Lines - (DL) with 139 monthly flights
  • JetBlue Airways - (B6) with 30 monthly flights

Are Logan Intl. Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
It is possible to get great last-minute deals from BOS to O’Hare Airport, but it’s also possible to miss out entirely! As many airlines publish prices up to a year in advance, it’s worth keeping an eye on fares early and being ready to pounce when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can rest easy knowing you’re always getting the latest offers.
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