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Did you mean flights from Chicago to Boston?

Flights from Boston to Chicago, United States Last modified: Sep 25, 2016 12:50 AM

Boston to Chicago Last modified: Sep 25, 2016 12:50 AM

We've scanned 23,629,223,180 round trip itineraries and found the cheapest flights from Boston to Chicago. American & JetBlue frequently offer the best deals on Boston to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

American
BOSCHI
Sat 10/29
nonstop
CHIBOS
Tue 11/1
nonstop
$87
Select
American
BOSCHI
Sat 10/29
nonstop
CHIBOS
Wed 11/2
nonstop
$87
Select
American
BOSCHI
Sat 10/29
nonstop
CHIBOS
Sat 11/5
nonstop
$87
Select
American
BOSCHI
Wed 11/2
nonstop
CHIBOS
Sat 11/5
nonstop
$87
Select
American
BOSCHI
Wed 11/2
nonstop
CHIBOS
Thu 11/3
nonstop
$87
Select
JetBlue
BOSCHI
Sat 10/29
nonstop
CHIBOS
Wed 11/2
nonstop
$87
Select
JetBlue
BOSCHI
Sat 10/29
nonstop
CHIBOS
Tue 11/1
nonstop
$87
Select
JetBlue
BOSCHI
Wed 11/30
nonstop
CHIBOS
Sat 12/3
nonstop
$87
Select
United
BOSCHI
Wed 10/12
nonstop
CHIBOS
Mon 10/17
nonstop
$87
Select
United
BOSCHI
Wed 10/12
nonstop
CHIBOS
Wed 10/19
nonstop
$87
Select
United
BOSCHI
Wed 10/19
nonstop
CHIBOS
Sat 10/22
nonstop
$87
Select
United
BOSCHI
Wed 10/19
nonstop
CHIBOS
Mon 10/24
nonstop
$87
Select
United
BOSCHI
Thu 10/20
nonstop
CHIBOS
Sat 10/22
nonstop
$87
Select
Spirit
BOSCHI
Thu 10/20
nonstop
CHIBOS
Tue 10/25
nonstop
$96
Select

How Much is a Flight from Boston to Chicago?

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 $99.

Where To Buy Cheap Flights from Boston to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we thinking FareCompare is the best place to find cheap tickets. Airlines can adjust prices for 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 found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Boston to Chicago?

The chart below shows up-to-date information regarding how far in advance to book your flight from Boston to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $117 $255
7-14 days $97 $246
14-21 days $87 $159
21-30 days $87 $179
30-60 days $87 $159
60-90 days $87 $192
90+ days $107 $159

Cheapest Day To Fly from Boston to Chicago

We've examined 23,636,053,052 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Boston to Chicago is Monday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$87 $87 $87 $87 $122 $87 $132

Compare Flight Prices from Boston to Chicago by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Boston to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
September Boston Chicago American 9/29/16 10/4/16 0 $117
October Boston Chicago American 10/29/16 11/1/16 0 $87
November Boston Chicago American 11/2/16 11/3/16 0 $87
December Boston Chicago United 12/14/16 12/14/16 0 $101
January Boston Chicago American 1/14/17 1/17/17 0 $107
February Boston Chicago American 2/1/17 2/4/17 0 $107
March Boston Chicago JetBlue 3/4/17 3/8/17 0 $107
April Boston Chicago JetBlue 4/22/17 4/29/17 0 $107

Cheap Last Minute Flights from Boston to Chicago

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Boston to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
25 26 27 28 29 30 1
$117
2 3 4 5 6 7 8
$117 $207
9 10 11 12 13 14 15
$207 $117
16 17 18 19 20 21 22
$117 $87
23 24 25 26 27 28 29
$87 $87
30 31 1 2 3 4 5
$87

Connecting Flights vs Direct Flights from Boston to Chicago

Flights between some cities may be significantly cheaper if you choose 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 $194.

The average price for direct flights from Boston to Chicago is $89.

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

Weekly Direct Flights from Boston to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 10 9 9 10 10 7 9 06:00 19:11
JetBlue 3 3 3 3 3 3 3 07:58 16:42
Spirit 1 1 1 1 1 1 1 13:16 13:16
United 10 10 9 10 10 5 10 06:15 20:17
Southwest 5 5 5 5 5 5 5 05:35 20:35

One Way Flights vs Round Trip Flights from Boston to Chicago

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 $139.

The average price for round trip flights from Boston to Chicago is $89.

Boston to Chicago Flight Questions

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

Question: How long is the flight from Boston to Chicago?
Answer: The average Boston to Chicago flight time is 2 hours and 47 minutes.
Question: How far is Chicago from Boston?
Answer: The distance from Boston to Chicago is 858 miles (1,380 kilometers).
Question: How common are direct flights from Boston to Chicago?
Answer: There are 191 direct flights from Boston to Chicago.
Question: What are the most popular Boston airlines for direct flights from Boston to Chicago?
Answer: United Airlines provides 33% of the non-stop flights between Boston and Chicago.
Question: What are the most popular connecting cities when flying from Boston to Chicago?
Answer: Newark, NJ

Airlines in Boston flying to Chicago Last modified: Sep 25, 2016 12:50 AMNumber of routes searched: 304Number of itineraries searched: 1,397,175

Wondering which airlines fly out of Boston to Chicago? We've gathered the average price of Boston airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Boston to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Delta CVG
Delta DTW
American LGA
American PHL
United IAD
Delta MSP
United EWR
American DFW
American DCA
Virgin America SFO
Virgin America LAX
United CLE
Alaska SEA
United IAH
United TPA
Alaska SAN
JetBlue FLL

Boston to Chicago Airports

These are the major commercial airports we're currently monitoring in Boston and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

More Cheap Flights

FlightsAirlineLowest Price
Flights from New York to Chicago American, Alaska, JetBlue, Delta, Spirit, United $107
Flights from Newark to Chicago American, JetBlue, Delta, United $117
Flights from Hartford to Chicago American, Delta, United $177
Flights from Providence to Chicago American $187
Flights from Westchester County to Chicago American, Delta, United $177
Flights from Albany to Chicago American, Delta, United $277
Flights from Burlington to Chicago JetBlue, Delta, United $241
Flights from Manchester to Chicago Delta, United $187
Flights from Portland to Chicago JetBlue, Delta, United $202
Flights from Long Island MacArthur to Chicago American $220
Flights from Newburgh to ChicagoCheck Dates
Flights from Bangor to Chicago Delta, United $498
Flights from New Haven to Chicago American $189
Flights from Nantucket to Chicago JetBlue Check Dates
Flights from New York to Atlanta American, JetBlue, Delta, Frontier, Spirit, United $109
Flights from New York to Los Angeles American, Alaska, JetBlue, Delta, Spirit, Sun Country, United, Virgin America $248
Flights from New York to Toronto American, Air Canada, Delta, United, WestJet $174
Flights from New York to Detroit American, JetBlue, Delta, Spirit $141
Flights from New York to London American, Air Berlin, Air Canada, Air France, Royal Air Maroc, Finnair, Alitalia, British Airways, Delta, Norwegian Shuttle, Aer Lingus, Icelandair, Iberia, KLM, Kuwait, Lufthansa, Swiss, El Al, China Eastern, Austrian, Qatar, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic, WestJet $384
Flights from New York to Milwaukee Delta $226
Flights from New York to Dallas - Ft Worth American, Alaska, JetBlue, Delta, Spirit, United, Virgin America $93
Flights from New York to Orlando American, JetBlue, Delta, Spirit, United $137
Flights from New York to Minneapolis - St Paul American, Delta, Spirit, Sun Country $232
Flights from New York to Miami American, Delta, Frontier $137
Flights from New York to Indianapolis American, Delta $143
Flights from New York to Las Vegas American, JetBlue, Delta, Spirit, Sun Country, United, Virgin America $192
Flights from Boston to Atlanta American, JetBlue, Delta, Spirit, United $157
Flights from New York to Charlotte American, JetBlue, Delta $127
Flights from New York to San Francisco American, Alaska, JetBlue, Delta, Sun Country, United, Virgin America $267
Flights from Boston to New York JetBlue, Delta $97
Cheap Flights from Boston to Chicago