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Did you mean flights from Chicago to Boston?

Cheap Flights from Boston to Chicago, IL, United States - BOS to CHI Last modified: Jun 27, 2016 6:51 PM

Popular flights from Boston to Chicago Last modified: Jun 27, 2016 6:51 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
BOSCHI
Tue 10/25
nonstop
CHIBOS
Wed 11/2
nonstop
$81
Select
American
BOSCHI
Tue 10/25
nonstop
CHIBOS
Tue 11/1
nonstop
$81
Select
United
BOSCHI
Wed 8/31
nonstop
CHIBOS
Wed 9/7
nonstop
$81
Select
United
BOSCHI
Wed 9/7
nonstop
CHIBOS
Tue 9/13
nonstop
$81
Select
United
BOSCHI
Tue 9/13
nonstop
CHIBOS
Tue 9/20
nonstop
$81
Select
United
BOSCHI
Tue 9/13
nonstop
CHIBOS
Wed 9/21
nonstop
$81
Select
United
BOSCHI
Wed 9/14
nonstop
CHIBOS
Wed 9/21
nonstop
$81
Select
Spirit
BOSCHI
Tue 8/23
nonstop
CHIBOS
Thu 8/25
nonstop
$88
Select
JetBlue
BOSCHI
Wed 7/13
nonstop
CHIBOS
Wed 7/20
nonstop
$204
Select
JetBlue
BOSCHI
Thu 7/14
nonstop
CHIBOS
Thu 7/21
nonstop
$204
Select
JetBlue
BOSCHI
Thu 7/14
nonstop
CHIBOS
Wed 7/20
nonstop
$204
Select
Alaska
BOSCHI
Wed 10/19
1 stop
CHIBOS
Fri 10/21
1 stop
$716
Select

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

We have collected flight cost data from across the web for travel from Boston to Chicago, and have found the average flight price for this trip to be $105.

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

Airlines can adjust prices for plane tickets from Boston to Chicago 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 Boston to Chicago

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

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $218 $251
7-14 days $197 $212
14-21 days $172 $195
21-30 days $157 $175
30-60 days $88 $175
60-90 days $81 $187
90+ days $81 $149

Cheapest Day To Fly from Boston to Chicago

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

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$99 $81 $81 $99 $149 $127 $99

Lowest Fares Chart By Month from Boston to Chicago

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

Month Origin Destination Carrier Depart Date Return Date Stops Price
June Boston Chicago United 6/29/16 7/5/16 0 $251
July Boston Chicago American 7/20/16 7/26/16 0 $157
August Boston Chicago United 8/31/16 9/7/16 0 $81
September Boston Chicago United 9/7/16 9/13/16 0 $81
October Boston Chicago American 10/25/16 11/1/16 0 $81
November Boston Chicago American 11/1/16 11/5/16 0 $81
December Boston Chicago American 12/5/16 12/8/16 0 $231
January Boston Chicago American 1/5/17 1/8/17 0 $261

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

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 Boston to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
26 27 28 29 30 1 2
$264
3 4 5 6 7 8 9
$264 $202
10 11 12 13 14 15 16
$202 $212
17 18 19 20 21 22 23
$212 $192
24 25 26 27 28 29 30
$192 $192
31 1 2 3 4 5 6
$192

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

Your Boston to Chicago 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 Boston to Chicago is $209.

The average price for non-stop flights from Boston to Chicago is $138.

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

Nonstop Flight Details from Boston to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 11 11 11 11 11 8 10 06:00 21:10
JetBlue 4 4 4 4 4 3 4 08:00 19:35
Spirit 1 1 1 1 1 1 1 13:15 13:15
United 9 9 9 9 9 6 7 06:30 20:00

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

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 Boston to Chicago. 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 Boston to Chicago is $57.

The average price for round trip flights from Boston to Chicago is $137.

More Cheap Flights

FlightsAirlineLowest Price
New York to Chicago American, Alaska, JetBlue, Spirit, United $81
Newark to Chicago American, Alaska, JetBlue, United $124
Hartford to Chicago American, United $320
Providence to Chicago American, Alaska, United $257
Westchester County to Chicago American, United $323
Albany to Chicago American, United $382
Burlington to Chicago American, United $359
Manchester to Chicago American, United $218
Portland to Chicago American, JetBlue, United $294
Long Island MacArthur to Chicago American, United $251
Newburgh to ChicagoCheck Dates
Bangor to Chicago American, United $489
New Haven to Chicago American $288
Nantucket to Chicago American, JetBlue, United $567
New York to Atlanta American, Alaska, Frontier, Spirit, United $147
New York to Los Angeles American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $270
New York to Toronto American, Air Canada, Alaska, JetBlue, Porter, United, WestJet $174
New York to Detroit American, JetBlue, Spirit, United $151
New York to London Aegean, American, Air Berlin, Air France, Alaska, Finnair, Alitalia, JetBlue, British Airways, airBaltic, Condor, Aer Lingus, Iberia, Meridiana, KLM, Kuwait, Lufthansa, LOT, Thomas Cook, Czech, Austrian, TAROM, SATA, XL Airways, SAS, Brussels, Jetairfly, Tap Portugal, United, Air Europa, Virgin Atlantic, Euro Atlantic $468
New York to Milwaukee American, Alaska, United $178
New York to Dallas - Ft Worth American, Alaska, JetBlue, Spirit, United, Virgin America $91
New York to Orlando American, JetBlue, Frontier, Spirit, United $200
New York to Minneapolis - St Paul American, Sun Country, United $270
New York to Miami American, Frontier, United $171
New York to Indianapolis American, United $143
New York to Las Vegas American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $253
Boston to Atlanta American, Spirit, United $143
New York to Charlotte American, JetBlue, United $154
New York to San Francisco American, Alaska, JetBlue, Sun Country, United, Virgin America $284
Boston to New York American, JetBlue $103

Airlines Flying from Boston to Chicago (BOS to CHI) Number of flights searched: 255Last modified: Jun 27, 2016 6:51 PM

Below are the different airlines that fly from Boston to Chicago 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 Boston to Chicago.

Boston to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
American JFK X X X X X X 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 CLE 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 Boston and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Boston to Chicago Flight Questions

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

Question: How long is a direct flight from Boston to Chicago?
Answer: The average Boston to Chicago flight time is 2 hours and 48 minutes.
Question: How many miles are there between Boston and Chicago?
Answer: The distance from Boston to Chicago is 864 miles.
Question: How common are direct flights from Boston to Chicago?
Answer: There are 165 direct flights from Boston to Chicago.
Question: What is the most popular airline for non-stop flights from Boston to Chicago?
Answer: American Airlines provides 44% of the non-stop flights between Boston and Chicago.
Question: What are the most popular connecting cities when flying from Boston to Chicago?
Answer: New York, NY
Boston (BOS) To Chicago, IL (CHI) Flights: Cheap Flights From Boston To Chicago | FareCompare.