S$78 Cheap Flights from Boston to Chicago

View S$78 flight on Tue, 20 Jan, 2026Opens in a new window

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

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Boston to Chicago (BOS-ORD)

Prices were available within the past 7 days and start at S$78 for one-way flights and S$206 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, 7 Dec - Tue, 16 Dec
BOS
Boston
ORD
Chicago
S$206 Return, found 1 day ago
S$206
Return
found 1 day ago
Select Delta flight, departing Sun, 7 Dec from Boston to Chicago, returning Tue, 16 Dec, priced at S$206 found 1 day ago
United
Sun, 7 Dec - Tue, 16 Dec
BOS
Boston
ORD
Chicago
S$220 Return, found 1 day ago
S$220
Return
found 1 day ago
Select United flight, departing Sun, 7 Dec from Boston to Chicago, returning Tue, 16 Dec, priced at S$220 found 1 day ago
Delta
Mon, 8 Dec - Sun, 14 Dec
BOS
Boston
ORD
Chicago
S$232 Return, found 2 days ago
S$232
Return
found 2 days ago
Select Delta flight, departing Mon, 8 Dec from Boston to Chicago, returning Sun, 14 Dec, priced at S$232 found 2 days ago
Delta
Sun, 7 Dec - Tue, 16 Dec
BOS
Boston
ORD
Chicago
S$241 Return, found 1 day ago
S$241
Return
found 1 day ago
Select Delta flight, departing Sun, 7 Dec from Boston to Chicago, returning Tue, 16 Dec, priced at S$241 found 1 day ago
United
Mon, 8 Dec - Sun, 14 Dec
BOS
Boston
ORD
Chicago
S$246 Return, found 2 days ago
S$246
Return
found 2 days ago
Select United flight, departing Mon, 8 Dec from Boston to Chicago, returning Sun, 14 Dec, priced at S$246 found 2 days ago
American Airlines
Sun, 7 Dec - Tue, 16 Dec
BOS
Boston
ORD
Chicago
S$252 Return, found 1 day ago
S$252
Return
found 1 day ago
Select American Airlines flight, departing Sun, 7 Dec from Boston to Chicago, returning Tue, 16 Dec, priced at S$252 found 1 day ago
United
Sun, 7 Dec - Tue, 16 Dec
BOS
Boston
ORD
Chicago
S$252 Return, found 1 day ago
S$252
Return
found 1 day ago
Select United flight, departing Sun, 7 Dec from Boston to Chicago, returning Tue, 16 Dec, priced at S$252 found 1 day ago
United
Sun, 7 Dec - Tue, 16 Dec
BOS
Boston
ORD
Chicago
S$254 Return, found 1 day ago
S$254
Return
found 1 day ago
Select United flight, departing Sun, 7 Dec from Boston to Chicago, returning Tue, 16 Dec, priced at S$254 found 1 day ago
Delta
Tue, 30 Dec - Fri, 2 Jan
BOS
Boston
ORD
Chicago
S$258 Return, found 21 hours ago
S$258
Return
found 21 hours ago
Select Delta flight, departing Tue, 30 Dec from Boston to Chicago, returning Fri, 2 Jan, priced at S$258 found 21 hours ago
United
Sun, 7 Dec - Tue, 16 Dec
BOS
Boston
ORD
Chicago
S$259 Return, found 1 day ago
S$259
Return
found 1 day ago
Select United flight, departing Sun, 7 Dec from Boston to Chicago, returning Tue, 16 Dec, priced at S$259 found 1 day ago

Black Friday Sale

Save up to 50% on select hotels
Book now

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

January is typically the cheapest month to fly

From S$93 - S$207 per traveller.
Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$206
Distance
1381 km
Average flight time
1 hour 59 mins

Flights from Boston to Chicago

There are several airlines that operate frequent flights from Boston (BOS) to Chicago (ORD) including

The earliest flight leaves Logan Intl. Airport at 05:00 and arrives at O'Hare Intl. Airport at 06:40. The last flight of the day departs Boston at 21:30 and arrives at Chicago at 23:21.

The flight distance from Boston to Chicago is about 1398 km, the shortest flight is 02 hours 40 minutes with Air Europa.

Expedia lets you search across the largest number of airlines and Chicago flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Boston Chicago flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Boston to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Boston to Chicago with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

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 S$206. 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.

Explore a world of travel with Expedia

Chicago Airports

Chicago

Boston Airports

Manchester

Manchester-Boston Regional to Chicago
S$605.30

Worcester

*Available to Expedia members.