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Cheap Flights from Chicago to Boston, MA, United States - CHI to BOS

Popular flights from Chicago to Boston

If your flight days are flexible and you looking for a good deal, our charts on cheap flights provide some insight regarding affordable flight options for your next big adventure.

American Airlines
Departure Date Return Date Lowest Price
Mar 8, 2016 Mar 15, 2016 $100
Mar 10, 2016 Mar 16, 2016 $100
Mar 15, 2016 Mar 22, 2016 $100
Mar 22, 2016 Mar 24, 2016 $100
JetBlue Airways
Departure Date Return Date Lowest Price
Feb 27, 2016 Mar 2, 2016 $109
Mar 1, 2016 Mar 5, 2016 $109
Apr 6, 2016 Apr 13, 2016 $109
Apr 13, 2016 Apr 26, 2016 $109
Spirit Airlines
Departure Date Return Date Lowest Price
Apr 19, 2016 Apr 23, 2016 $112
May 6, 2016 May 8, 2016 $112
May 6, 2016 May 9, 2016 $112
United Airlines
Departure Date Return Date Lowest Price
Mar 5, 2016 Mar 8, 2016 $103
Mar 8, 2016 Mar 16, 2016 $103
Mar 8, 2016 Mar 15, 2016 $103
Mar 9, 2016 Mar 17, 2016 $103
Mar 10, 2016 Mar 16, 2016 $103

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 $102.

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 $248 $261
7-14 days $103 $145
14-21 days $103 $145
21-30 days $100 $143
30-60 days $100 $143
60-90 days $103 $143
90+ days $103 $146

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
$103 $100 $103 $100 $103 $103 $103

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
February Chicago Boston American 2/25/16 2/28/16 0 $103
March Chicago Boston American 3/8/16 3/15/16 0 $100
April Chicago Boston United 4/2/16 4/5/16 0 $103
May Chicago Boston United 5/7/16 5/10/16 0 $103
June Chicago Boston United 6/4/16 6/11/16 0 $139
July Chicago Boston American 7/12/16 7/17/16 0 $163
August Chicago Boston American 8/17/16 8/24/16 0 $223
September Chicago Boston United 9/9/16 9/11/16 0 $139

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
14 15 16 17 18 19 20
$203
21 22 23 24 25 26 27
$203 $103
28 29 1 2 3 4 5
$103 $103
6 7 8 9 10 11 12
$103 $103
13 14 15 16 17 18 19
$103 $139
20 21 22 23 24 25 26
$139

TIPSave $62 by flying into New York instead of Boston from Chicago

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 $163.

The average price for non-stop flights from Chicago to Boston is $119.

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 8 8 8 8 8 7 8 06:00 21:55
JetBlue 3 3 3 3 3 2 2 09:36 18:46
United 7 7 7 7 7 5 7 06:05 20:55

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 $52.

The average price for round trip flights from Chicago to Boston is $119.

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 15 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 121 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 45% of the non-stop flights between Chicago and Boston.
Question: What are the most popular connecting cities when flying from Chicago to Boston?
Answer: New York, NY

Airlines Flying from Chicago to Boston (CHI to BOS)

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 JFK 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
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, JetBlue, Spirit, United $78
Chicago to Providence American, United $173
Chicago to Manchester American, United $188
Chicago to Newark American, JetBlue, United $188
Chicago to Washington American, JetBlue, Frontier, United $79
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $76
Chicago to Hartford American, United $270
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $127
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $94
Chicago to Philadelphia American, Frontier, Spirit, United $78
Chicago to Atlanta American, Alaska, Spirit, United $78
Chicago to Portland American, JetBlue, United $255

Cheap International Flights from Chicago - CHI

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

Cheap Domestic Flights to Boston - BOS

FlightsAirlineLowest Price
Indianapolis to Boston American, JetBlue, United $198
Milwaukee to Boston American, Alaska, United $199
Madison to Boston American, Alaska, United $290
Green Bay to Boston American, United $406
Moline to Boston American, United $312
Lansing to Boston Alaska, United $166
Appleton to Boston United $442
Grand Rapids to Boston American, United $172
Kalamazoo to Boston American, United $191
Peoria to Boston American, United $309
Bloomington - Normal to Boston American $312
South Bend to Boston United $312
Champaign to Boston American, United $311
Ft Wayne to Boston American, United $268
Dubuque to Boston American $440
Springfield to Boston American, United $322
Toledo to Boston American $321
Cheap Flights from Chicago to Boston, MA, United States, from $100 Round trip from CHI to BOS