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Did you mean flights from Boston to Chicago?

Cheap Flights from Chicago to Boston, MA, United States - CHI to BOS Last modified: Jun 26, 2016 6:52 PM

Popular flights from Chicago to Boston Last modified: Jun 26, 2016 6:52 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
Oct 21, 2016 Oct 25, 2016 $119
Oct 22, 2016 Oct 25, 2016 $119
JetBlue Airways
Departure Date Return Date Lowest Price
Jul 19, 2016 Jul 26, 2016 $204
Jul 20, 2016 Jul 26, 2016 $204
Jul 26, 2016 Aug 3, 2016 $204
Spirit Airlines
Departure Date Return Date Lowest Price
Aug 23, 2016 Aug 24, 2016 $91
Aug 23, 2016 Aug 25, 2016 $91
Aug 24, 2016 Aug 25, 2016 $91
United Airlines
Departure Date Return Date Lowest Price
Sep 7, 2016 Sep 13, 2016 $81
Sep 7, 2016 Sep 14, 2016 $81
Sep 7, 2016 Sep 21, 2016 $81
Sep 13, 2016 Sep 20, 2016 $81
Sep 13, 2016 Sep 14, 2016 $81

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 $119.

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 $224 $280
7-14 days $197 $270
14-21 days $177 $195
21-30 days $167 $175
30-60 days $91 $212
60-90 days $81 $252
90+ days $81 $252

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
$127 $81 $81 $99 $144 $127 $174

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
June Chicago Boston American 6/27/16 7/3/16 0 $224
July Chicago Boston Spirit 7/20/16 7/26/16 0 $167
August Chicago Boston Spirit 8/23/16 8/24/16 0 $91
September Chicago Boston United 9/7/16 9/13/16 0 $81
October Chicago Boston American 10/25/16 11/1/16 0 $81
November Chicago Boston American 11/1/16 11/8/16 0 $81
December Chicago Boston American 12/2/16 12/4/16 0 $231
January Chicago Boston American 1/28/17 2/1/17 0 $261

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
26 27 28 29 30 1 2
$270
3 4 5 6 7 8 9
$270 $202
10 11 12 13 14 15 16
$202 $192
17 18 19 20 21 22 23
$192 $172
24 25 26 27 28 29 30
$172 $192
31 1 2 3 4 5 6
$192
TIPSave $71 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 $220.

The average price for non-stop flights from Chicago to Boston is $134.

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 21:20

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 $62.

The average price for round trip flights from Chicago to Boston is $134.

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 167 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: 210Last modified: Jun 26, 2016 6:52 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 DCA 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 BNA 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 $306
Chicago to Manchester American, United $301
Chicago to Newark American, JetBlue, United $124
Chicago to Washington American, Alaska, Frontier, United $137
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $123
Chicago to Hartford American, United $338
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $137
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $81
Chicago to Philadelphia American, Alaska, Frontier, Spirit, United $87
Chicago to Atlanta American, Frontier, Spirit, United $81
Chicago to Portland American, JetBlue, United $294

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Toronto Air Choice One, American, Air Canada, Alaska, JetBlue, Frontier, Public Charters, Porter, United, WestJet $237

Cheap Domestic Flights to Boston - BOS

FlightsAirlineLowest Price
Indianapolis to Boston American, Alaska, JetBlue, United $207
Milwaukee to Boston American, Alaska, United $242
Madison to Boston American, Alaska, United $326
Green Bay to Boston American, United $372
Moline to Boston American, Alaska, United $250
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 $250
Bloomington - Normal to Boston American $306
South Bend to Boston United $386
Champaign to Boston American $265
Ft Wayne to Boston American, United $369
Dubuque to Boston American $379
Springfield to Boston American, United $250
Toledo to Boston American $320
Cheap Flights from Chicago to Boston, MA, United States, from $81 Round trip from CHI to BOS