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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: Jul 26, 2016 12:51 AM

Popular flights from Boston to Chicago Last modified: Jul 26, 2016 12:51 AM

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.

United
BOSCHI
Wed 8/31
nonstop
CHIBOS
Tue 9/13
nonstop
$77
Select
United
BOSCHI
Wed 9/7
nonstop
CHIBOS
Tue 9/13
nonstop
$77
Select
United
BOSCHI
Wed 9/7
nonstop
CHIBOS
Wed 9/14
nonstop
$77
Select
United
BOSCHI
Tue 9/13
nonstop
CHIBOS
Tue 9/20
nonstop
$77
Select
United
BOSCHI
Tue 9/20
nonstop
CHIBOS
Tue 10/4
nonstop
$77
Select
Spirit
BOSCHI
Tue 8/30
nonstop
CHIBOS
Sat 9/10
nonstop
$87
Select
Spirit
BOSCHI
Tue 8/30
nonstop
CHIBOS
Wed 9/7
nonstop
$87
Select
Spirit
BOSCHI
Tue 8/30
nonstop
CHIBOS
Wed 9/7
nonstop
$87
Select
Spirit
BOSCHI
Wed 8/31
nonstop
CHIBOS
Tue 9/13
nonstop
$87
Select
Spirit
BOSCHI
Wed 8/31
nonstop
CHIBOS
Wed 9/7
nonstop
$87
Select
American
BOSCHI
Thu 11/3
nonstop
CHIBOS
Sat 11/5
nonstop
$97
Select
JetBlue
BOSCHI
Tue 9/6
nonstop
CHIBOS
Sat 9/10
nonstop
$187
Select
JetBlue
BOSCHI
Tue 9/6
nonstop
CHIBOS
Thu 9/8
nonstop
$187
Select
JetBlue
BOSCHI
Wed 9/7
nonstop
CHIBOS
Fri 9/9
nonstop
$187
Select
JetBlue
BOSCHI
Wed 9/7
nonstop
CHIBOS
Sat 9/10
nonstop
$187
Select
JetBlue
BOSCHI
Thu 9/8
nonstop
CHIBOS
Mon 9/12
nonstop
$187
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 $93.

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 $212 $310
7-14 days $157 $280
14-21 days $177 $257
21-30 days $147 $257
30-60 days $77 $219
60-90 days $87 $237
90+ days $77 $236

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
$107 $77 $77 $87 $107 $87 $107

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
July Boston Chicago United 7/31/16 8/15/16 0 $237
August Boston Chicago United 8/31/16 9/13/16 0 $77
September Boston Chicago United 9/7/16 9/13/16 0 $77
October Boston Chicago United 10/25/16 10/26/16 0 $77
November Boston Chicago American 11/3/16 11/5/16 0 $97
December Boston Chicago JetBlue 12/5/16 12/12/16 0 $197
January Boston Chicago United 1/4/17 1/7/17 0 $197
February Boston Chicago United 2/4/17 2/11/17 0 $197

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
24 25 26 27 28 29 30
$246
31 1 2 3 4 5 6
$246 $217
7 8 9 10 11 12 13
$217 $216
14 15 16 17 18 19 20
$216 $167
21 22 23 24 25 26 27
$167 $177
28 29 30 31 1 2 3
$177

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 $237.

The average price for non-stop flights from Boston to Chicago is $117.

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 10 10 8 10 06:00 21:10
JetBlue 4 4 4 4 4 2 4 08:00 19:35
Spirit 1 1 1 1 1 1 1 13:11 13:11
United 9 9 9 9 9 6 8 06:00 20:15

More Cheap Flights

FlightsAirlineLowest Price
New York to Chicago American, Alaska, JetBlue, Spirit, United $77
Newark to Chicago American, Alaska, JetBlue, United $117
Hartford to Chicago American, United $333
Providence to Chicago American, United $187
Westchester County to Chicago American, United $332
Albany to Chicago American, United $339
Burlington to Chicago American, United $296
Manchester to Chicago American, United $187
Portland to Chicago American, JetBlue, United $260
Long Island MacArthur to Chicago American $215
Newburgh to ChicagoCheck Dates
Bangor to Chicago American, United $344
New Haven to Chicago American $239
Nantucket to Chicago American, JetBlue, United Check Dates
New York to Atlanta American, Alaska, Frontier, Spirit, United $107
New York to Los Angeles American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $246
New York to Toronto American, Air Canada, Alaska, JetBlue, Porter, United, WestJet $173
New York to Detroit American, JetBlue, Spirit, United $139
New York to London Aegean, American, Air Berlin, Air France, Alaska, Finnair, Alitalia, JetBlue, British Airways, airBaltic, Condor, Aer Lingus, Eurowings, Bulgaria Air, Iberia, Meridiana, KLM, Kuwait, Lufthansa, LOT, Thomas Cook, Czech, Austrian, TAROM, SATA, XL Airways, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic, FlexFlight $409
New York to Milwaukee American, Alaska, United $147
New York to Dallas - Ft Worth American, Alaska, JetBlue, Spirit, United, Virgin America $94
New York to Orlando American, JetBlue, Spirit, United $197
New York to Minneapolis - St Paul American, JetBlue, Sun Country, United $197
New York to Miami American, Frontier, United $137
New York to Indianapolis American, United $142
New York to Las Vegas American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $244
Boston to Atlanta American, Spirit, United $119
New York to Charlotte American, JetBlue, United $154
New York to San Francisco American, Alaska, JetBlue, Sun Country, United, Virgin America $286
Boston to New York American, JetBlue $97

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 47 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 153 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 43% 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.