$70 Cheap Flights from Boston (BOS) to Chicago (CHI)

View $70 flight on Tue, May 12, 2026Opens in a new window

Popular airlines from Logan International Airport (BOS) to Chicago

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Cheap Flights from Boston to Chicago (BOS-CHI)

Prices were available within the past 7 days and start at $70 for one-way flights and $139 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Apr 29 - Tue, May 5
BOS
Boston
RFD
Rockford
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Apr 29 from Boston to Rockford, returning Tue, May 5, priced at $139 found 2 days ago
Frontier Airlines
Sat, May 9 - Tue, May 12
BOS
Boston
MDW
Chicago
$140 Roundtrip, found 1 hour ago
$140
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 9 from Boston to Chicago, returning Tue, May 12, priced at $140 found 1 hour ago
Frontier Airlines
Tue, May 5 - Thu, May 7
BOS
Boston
ORD
Chicago
$140 Roundtrip, found 2 hours ago
$140
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Boston to Chicago, returning Thu, May 7, priced at $140 found 2 hours ago
Frontier Airlines
Tue, May 5 - Tue, May 12
BOS
Boston
ORD
Chicago
$146 Roundtrip, found 15 hours ago
$146
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Boston to Chicago, returning Tue, May 12, priced at $146 found 15 hours ago
Southwest Airlines
Wed, Apr 22 - Wed, Apr 29
BOS
Boston
MDW
Chicago
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Apr 22 from Boston to Chicago, returning Wed, Apr 29, priced at $147 found 2 days ago
Frontier Airlines
Tue, May 5 - Thu, May 7
BOS
Boston
ORD
Chicago
$150 Roundtrip, found 2 hours ago
$150
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Boston to Chicago, returning Thu, May 7, priced at $150 found 2 hours ago
American Airlines
Wed, Apr 29 - Sat, May 2
BOS
Boston
RFD
Rockford
$153 Roundtrip, found 2 days ago
$153
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Apr 29 from Boston to Rockford, returning Sat, May 2, priced at $153 found 2 days ago
Southwest Airlines
Wed, May 6 - Sat, May 9
BOS
Boston
MDW
Chicago
$153 Roundtrip, found 2 days ago
$153
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, May 6 from Boston to Chicago, returning Sat, May 9, priced at $153 found 2 days ago
JetBlue Airways
Fri, May 8 - Tue, May 12
BOS
Boston
ORD
Chicago
$164 Roundtrip, just found
$164
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, May 8 from Boston to Chicago, returning Tue, May 12, priced at $164 just found
Delta
Wed, Aug 5 - Tue, Aug 11
BOS
Boston
ORD
Chicago
$167 Roundtrip, just found
$167
Roundtrip
just found
Select Delta flight, departing Wed, Aug 5 from Boston to Chicago, returning Tue, Aug 11, priced at $167 just found

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $177
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $177
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $170
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $170
Select flight to Greater Rockford RFD. Cheapest option available. Average driving time to city center is 1 hour 30 minutes. Flights from $167
RFD
Greater Rockford
Cheapest
Average driving time to city center1 h 30 min
Flights from $167

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 $139. 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 901 mi. 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.

Travel information

Origin airport
Logan Intl.
Destination airport
Greater Rockford
Roundtrip price
$138
Distance
922 mi

*Flight schedules are subject to change.

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