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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: Aug 28, 2016 1:03 AM

Popular flights from Boston to Chicago Last modified: Aug 28, 2016 1:03 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.

Spirit
BOSCHI
Sat 10/15
nonstop
CHIBOS
Wed 10/19
nonstop
$86
Select
Spirit
BOSCHI
Thu 10/20
nonstop
CHIBOS
Thu 10/27
nonstop
$86
Select
Spirit
BOSCHI
Tue 10/25
nonstop
CHIBOS
Tue 11/1
nonstop
$86
Select
American
BOSCHI
Sun 9/4
nonstop
CHIBOS
Fri 9/9
nonstop
$135
Select
American
BOSCHI
Thu 9/8
nonstop
CHIBOS
Wed 9/14
nonstop
$135
Select
American
BOSCHI
Tue 9/20
nonstop
CHIBOS
Wed 9/21
nonstop
$135
Select
American
BOSCHI
Sat 10/15
nonstop
CHIBOS
Wed 10/19
nonstop
$135
Select
American
BOSCHI
Sat 10/22
nonstop
CHIBOS
Sun 10/23
nonstop
$135
Select
United
BOSCHI
Sun 9/4
nonstop
CHIBOS
Sun 9/11
nonstop
$135
Select
United
BOSCHI
Sun 9/4
nonstop
CHIBOS
Fri 9/9
nonstop
$135
Select
United
BOSCHI
Thu 9/8
nonstop
CHIBOS
Wed 9/14
nonstop
$135
Select
United
BOSCHI
Tue 9/20
nonstop
CHIBOS
Wed 9/21
nonstop
$135
Select
JetBlue
BOSCHI
Sat 9/10
nonstop
CHIBOS
Tue 9/13
nonstop
$177
Select
JetBlue
BOSCHI
Sat 9/10
nonstop
CHIBOS
Mon 9/12
nonstop
$177
Select
JetBlue
BOSCHI
Thu 9/22
nonstop
CHIBOS
Tue 9/27
nonstop
$177
Select
JetBlue
BOSCHI
Sat 9/24
nonstop
CHIBOS
Mon 9/26
nonstop
$177
Select
JetBlue
BOSCHI
Tue 9/27
nonstop
CHIBOS
Tue 10/4
nonstop
$177
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 $101.

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 $157 $282
7-14 days $109 $237
14-21 days $87 $237
21-30 days $87 $239
30-60 days $86 $231
60-90 days $87 $241
90+ days $175 $241

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
$87 $86 $87 $86 $135 $86 $135

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
August Boston Chicago American 8/30/16 8/31/16 0 $167
September Boston Chicago Spirit 9/17/16 9/20/16 0 $87
October Boston Chicago Spirit 10/15/16 10/19/16 0 $86
November Boston Chicago Spirit 11/1/16 11/3/16 0 $87
December Boston Chicago American 12/1/16 12/5/16 0 $177
January Boston Chicago American 1/23/17 1/30/17 0 $175
February Boston Chicago American 2/6/17 2/15/17 0 $175
March Boston Chicago American 3/1/17 3/8/17 0 $175

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
28 29 30 31 1 2 3
$187
4 5 6 7 8 9 10
$187 $109
11 12 13 14 15 16 17
$109 $87
18 19 20 21 22 23 24
$87 $87
25 26 27 28 29 30 1
$87 $87
2 3 4 5 6 7 8
$87

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 $133.

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 10 9 9 10 10 7 9 06:00 19:11
JetBlue 3 3 3 3 3 2 3 07:58 16:42
Spirit 1 1 1 1 1 1 1 13:16 13:16
United 9 9 9 9 9 5 8 06:05 19:45

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 $67.

The average price for round trip flights from Boston to Chicago is $133.

More Cheap Flights

FlightsAirlineLowest Price
New York to Chicago American, Alaska, JetBlue, Delta, Spirit, United $126
Newark to Chicago American, JetBlue, Delta, United $147
Hartford to Chicago American, Delta, United $304
Providence to Chicago American, Delta, United $177
Westchester County to Chicago American, Delta, United $340
Albany to Chicago American, Delta, United $305
Burlington to Chicago American, Delta, United $380
Manchester to Chicago American, Delta, United $177
Portland to Chicago American, JetBlue, Delta, United $296
Long Island MacArthur to Chicago American $264
Newburgh to ChicagoCheck Dates
Bangor to Chicago American, Delta, United $331
New Haven to Chicago American $250
Nantucket to Chicago American, JetBlue, Delta, United $500
New York to Atlanta American, Delta, Frontier, Spirit, United $173
New York to Los Angeles American, Alaska, JetBlue, Delta, Spirit, Sun Country, United, Virgin America $262
New York to Toronto American, Air Canada, Alaska, Delta, United, WestJet $174
New York to Detroit American, JetBlue, Delta, Spirit, United $140
New York to London American, Air Berlin, Air Canada, Air France, Air India, AeroMexico, Royal Air Maroc, Avianca, Finnair, Alitalia, British Airways, airBaltic, Cathay, China Southern, Delta, Norwegian Shuttle, Aer Lingus, Emirates, Etihad, Icelandair, Iberia, Meridiana, Latam Airlines Brasil, Korean, KLM, Kuwait, Lufthansa, LOT, Swiss, El Al, Egyptair, China Eastern, Austrian, UIA, Qatar, TAROM, South African, Brussels, Aeroflot, Saudi Arabian, Turkish, Tap Portugal, United, Air Europa, Virgin Atlantic, WestJet $416
New York to Milwaukee American, Delta, United $184
New York to Dallas - Ft Worth American, Alaska, JetBlue, Delta, Spirit, United, Virgin America $77
New York to Orlando American, JetBlue, Delta, Spirit, United $109
New York to Minneapolis - St Paul American, Delta, Sun Country, United $258
New York to Miami American, Delta, Frontier, United $156
New York to Indianapolis American, Delta, United $141
New York to Las Vegas American, Alaska, JetBlue, Delta, Frontier, Spirit, Sun Country, United, Virgin America $254
Boston to Atlanta American, Delta, Spirit, United $101
New York to Charlotte American, JetBlue, Delta $127
New York to San Francisco American, Alaska, JetBlue, Delta, Sun Country, United, Virgin America $311
Boston to New York American, JetBlue, Delta $96

Airlines Flying from Boston to Chicago (BOS to CHI) Number of flights searched: 260Last modified: Aug 28, 2016 1:03 AM

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 LGA 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 DTW 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 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 149 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 42% 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.