S$79 Cheap Flights from Boston to Chicago

View S$79 flight on Wed, 26 Mar,2025Opens in a new window

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Cheap Flights from Boston to Chicago (BOS-CHI)

Prices were available within the past 7 days and start at S$79 for one-way flights and S$210 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 10 Apr - Mon, 14 Apr
BOS
Boston
ORD
Chicago
S$210 Return, found 2 days ago
S$210
Return
found 2 days ago
Select Delta flight, departing Thu, 10 Apr from Boston to Chicago, returning Mon, 14 Apr, priced at S$210 found 2 days ago
Delta
Sat, 31 May - Wed, 4 Jun
BOS
Boston
ORD
Chicago
S$231 Return, found 1 day ago
S$231
Return
found 1 day ago
Select Delta flight, departing Sat, 31 May from Boston to Chicago, returning Wed, 4 Jun, priced at S$231 found 1 day ago
Delta
Sat, 31 May - Wed, 4 Jun
BOS
Boston
ORD
Chicago
S$237 Return, found 1 day ago
S$237
Return
found 1 day ago
Select Delta flight, departing Sat, 31 May from Boston to Chicago, returning Wed, 4 Jun, priced at S$237 found 1 day ago
Delta
Thu, 10 Apr - Mon, 14 Apr
BOS
Boston
ORD
Chicago
S$252 Return, found 2 days ago
S$252
Return
found 2 days ago
Select Delta flight, departing Thu, 10 Apr from Boston to Chicago, returning Mon, 14 Apr, priced at S$252 found 2 days ago
United
Thu, 10 Apr - Mon, 14 Apr
BOS
Boston
ORD
Chicago
S$258 Return, found 2 days ago
S$258
Return
found 2 days ago
Select United flight, departing Thu, 10 Apr from Boston to Chicago, returning Mon, 14 Apr, priced at S$258 found 2 days ago
American Airlines
Sat, 31 May - Wed, 4 Jun
BOS
Boston
ORD
Chicago
S$264 Return, found 1 day ago
S$264
Return
found 1 day ago
Select American Airlines flight, departing Sat, 31 May from Boston to Chicago, returning Wed, 4 Jun, priced at S$264 found 1 day ago
Delta
Thu, 3 Apr - Mon, 7 Apr
BOS
Boston
ORD
Chicago
S$265 Return, found 2 days ago
S$265
Return
found 2 days ago
Select Delta flight, departing Thu, 3 Apr from Boston to Chicago, returning Mon, 7 Apr, priced at S$265 found 2 days ago
United
Fri, 4 Apr - Mon, 7 Apr
BOS
Boston
ORD
Chicago
S$271 Return, found 5 days ago
S$271
Return
found 5 days ago
Select United flight, departing Fri, 4 Apr from Boston to Chicago, returning Mon, 7 Apr, priced at S$271 found 5 days ago
Delta
Thu, 10 Apr - Mon, 14 Apr
BOS
Boston
ORD
Chicago
S$272 Return, found 2 days ago
S$272
Return
found 2 days ago
Select Delta flight, departing Thu, 10 Apr from Boston to Chicago, returning Mon, 14 Apr, priced at S$272 found 2 days ago
United
Sat, 31 May - Wed, 4 Jun
BOS
Boston
ORD
Chicago
S$278 Return, found 1 day ago
S$278
Return
found 1 day ago
Select United flight, departing Sat, 31 May from Boston to Chicago, returning Wed, 4 Jun, priced at S$278 found 1 day ago
Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
S$210
Distance
1381 km

Flights from Boston to Illinois

When looking for plane tickets from Boston to Illinois, the ease and convenience of using Expedia simply can’t be beat. With tons of departure points and flights options from the top airline carriers, Expedia gives you the widest array of cheap flights to Illinois. Look for BOS to CHI airfare with the assurance that you have the largest online travel agency working for you.

Expedia lets you search across the largest number of airlines and Illinois 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 Illinois 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 Illinois trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Illinois 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 Illinois 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 (BOS) to Chicago, IL (CHI-All Airports)?
Pack your bags, because round-trip journeys from Logan Intl. Airport to Chicago, IL (CHI-All Airports) start from S$210. That’s based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can increase quickly, so book now to get the best deal. 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 to Chicago, IL (CHI-All Airports)?
Each air carrier has its own terms and conditions. If you decide to cancel your trip, visit our Customer Service Portal.
How do I find cheap flights from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports) 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 Chicago, IL (CHI-All Airports) flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports)?
The distance from Logan Intl. Airport (BOS) (BOS) to Chicago, IL (CHI-All Airports) (CHI) is 1,450 kilometres. You’ll be stepping off the plane and collecting your baggage from the carousel in next to no time.
Which airlines fly direct from BOS to Chicago, IL (CHI-All Airports)?
With so many airlines to choose from, you’ll be able to find your perfect flight from Logan Intl. Airport to Chicago, IL (CHI-All Airports) in a few clicks. These are some of the most popular carriers that fly directly between these airports:

  • American Airlines - (AA) with 230 monthly flights
  • United Airlines - (UA) with 178 monthly flights
  • Delta Air Lines - (DL) with 139 monthly flights
  • Southwest Airlines - (WN) with 121 monthly flights

Are BOS to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
It is possible to find a great last-minute deal from BOS to Chicago, IL (CHI-All Airports), but there’s no guarantee. As many airlines release prices up to 12 months in advance, it’s worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals often, so you can rest easy knowing you’re always seeing the latest offers.
*Available to Expedia members.