Flights
Hotels
From
To
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.
Flights
Hotels
Round-trip
One-way
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.

Cheap Flights from Chicago to Boston, MA, United States - CHI to BOS Last modified: May 30, 2016 6:54 PM

Popular flights from Chicago to Boston Last modified: May 30, 2016 6:54 PM

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

American Airlines
Departure Date Return Date Lowest Price
Jun 8, 2016 Jun 14, 2016 $105
Jun 8, 2016 Jun 15, 2016 $105
JetBlue Airways
Departure Date Return Date Lowest Price
Jun 3, 2016 Jun 6, 2016 $137
Spirit Airlines
Departure Date Return Date Lowest Price
Sep 10, 2016 Sep 24, 2016 $115
United Airlines
Departure Date Return Date Lowest Price
Jun 8, 2016 Jun 15, 2016 $108

How Much Does it Cost to Fly from Chicago to Boston (CHI to BOS)?

We have collected flight cost data from across the web for travel from Chicago to Boston, and have found the average flight price for this trip to be $130.

When Can I Buy the Cheapest Flight from Chicago to Boston (CHI to BOS)?

Airlines can adjust prices for plane tickets from Chicago to Boston based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Chicago to Boston

The chart below shows up-to-date information regarding how far in advance a flight from Chicago to Boston should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $115 $193
7-14 days $105 $163
14-21 days $125 $191
21-30 days $147 $210
30-60 days $147 $204
60-90 days $117 $212
90+ days $115 $212

Cheapest Day To Fly from Chicago to Boston

The chart below shows up-to-date information regarding the cheapest days to fly from Chicago to Boston.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$157 $117 $105 $117 $117 $115 $182

Lowest Fares Chart By Month from Chicago to Boston

The chart below shows the lowest fare by month when flying from Chicago to Boston.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Chicago Boston United 5/31/16 6/7/16 0 $157
June Chicago Boston American 6/8/16 6/14/16 0 $105
July Chicago Boston JetBlue 7/12/16 7/19/16 0 $147
August Chicago Boston Spirit 8/23/16 8/24/16 0 $117
September Chicago Boston Spirit 9/10/16 9/24/16 0 $115
October Chicago Boston Spirit 10/1/16 10/3/16 0 $117
November Chicago Boston Spirit 11/1/16 11/2/16 0 $115
December Chicago Boston American 12/1/16 12/8/16 0 $147

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to Boston

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Chicago to Boston.

Next 30 Days

SunMonTueWedThuFriSat
29 30 31 1 2 3 4
$117
5 6 7 8 9 10 11
$117 $164
12 13 14 15 16 17 18
$164 $176
19 20 21 22 23 24 25
$176 $182
26 27 28 29 30 1 2
$182 $192
3 4 5 6 7 8 9
$192

Non-Stop vs Connecting Flights from Chicago to Boston (CHI to BOS)

Your Chicago to Boston flight can be significantly cheaper by choosing a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Chicago to Boston is $221.

The average price for non-stop flights from Chicago to Boston is $139.

The chart below shows up to date information regarding non-stop flights from Chicago to Boston.

Nonstop Flight Details from Chicago to Boston
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 11 11 11 11 11 9 11 06:00 21:44
JetBlue 4 4 4 4 4 3 4 07:00 19:15
Spirit 1 1 1 1 1 1 1 14:08 14:08
United 9 9 9 9 9 5 8 06:00 21:15

Round Trip vs One Way Flights from Chicago to Boston (CHI to BOS)

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Boston. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Boston is $69.

The average price for round trip flights from Chicago to Boston is $139.

Chicago to Boston Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is a direct flight from Chicago to Boston?
Answer: The average Chicago to Boston flight time is 2 hours and 20 minutes.
Question: How many miles are there between Chicago and Boston?
Answer: The distance from Chicago to Boston is 864 miles.
Question: How common are direct flights from Chicago to Boston?
Answer: There are 164 direct flights from Chicago to Boston.
Question: What is the most popular airline for non-stop flights from Chicago to Boston?
Answer: American Airlines provides 44% of the non-stop flights between Chicago and Boston.
Question: What are the most popular connecting cities when flying from Chicago to Boston?
Answer: Atlanta, GA

Airlines Flying from Chicago to Boston (CHI to BOS) Number of flights searched: 222Last modified: May 30, 2016 6:54 PM

Below are the different airlines that fly from Chicago to Boston with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Chicago to Boston.

Chicago to Boston
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
American PHL X
JetBlue - X X X X X X X
JetBlue JFK X X X X X X X
Delta MSP X X X X X X X
Spirit - X X X X X X X
United - X X X X X X X
United EWR X X X X X X X
Southwest - X X X X X X X
Southwest BWI X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and Boston, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to New York American, Alaska, JetBlue, Spirit, United $81
Chicago to Providence American, United $209
Chicago to Manchester American, United $201
Chicago to Newark American, JetBlue, United $172
Chicago to Washington American, Alaska, Frontier, United $98
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $147
Chicago to Hartford American, United $339
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $118
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $183
Chicago to Philadelphia American, Frontier, Spirit, United $108
Chicago to Atlanta American, Spirit, United $81
Chicago to Portland American, JetBlue, United $298

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Toronto Air Choice One, American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet $198

Cheap Domestic Flights to Boston - BOS

FlightsAirlineLowest Price
Indianapolis to Boston American, Alaska, JetBlue, Frontier, United $201
Milwaukee to Boston American, Alaska, United $204
Madison to Boston American, Alaska, United $326
Green Bay to Boston American, United $372
Moline to Boston American, United $244
Lansing to Boston American, Alaska, United $256
Appleton to Boston United $372
Grand Rapids to Boston American, Alaska, United $208
Kalamazoo to Boston American, United $372
Peoria to Boston American, United $244
Bloomington - Normal to Boston American $244
South Bend to Boston United $410
Champaign to Boston American $372
Ft Wayne to Boston American, United $337
Dubuque to Boston American $502
Springfield to Boston American, United $244
Toledo to Boston American $431
Cheap Flights from Chicago to Boston, MA, United States, from $105 Round trip from CHI to BOS