Flights from Boston to Chicago, United States

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Did you mean flights from Chicago to Boston?

Boston to Chicago Last modified: Aug 20, 2019 3:26 -04:00

We've scanned 48,195,047,545 round trip itineraries and found the cheapest flights to Chicago. JetBlue & American frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Thu 9/26
Sat 9/28
Tue 8/27
Tue 8/27
Major Airlines
Tue 10/1
Mon 10/7
Tue 9/10
Wed 9/11
Tue 9/17
Tue 9/24

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 $147.

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 think 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 $153 $160
7-14 days $147 $160
14-21 days $147 $156
21-30 days $147 $155
30-60 days $142 $160
60-90 days $147 $155
90+ days $147 $156

Cheapest Day To Fly from Boston to Chicago

We've examined 57,595,778,181 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 Sunday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday

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
August Boston Chicago American 8/26/19 8/28/19 0 $153
September Boston Chicago American 9/21/19 9/22/19 0 $147
October Boston Chicago American 10/26/19 10/28/19 0 $147
November Boston Chicago American 11/1/19 11/4/19 0 $147
December Boston Chicago American 12/5/19 12/7/19 0 $147
January Boston Chicago American 1/4/20 1/12/20 0 $153
February Boston Chicago American 2/11/20 2/14/20 0 $147
March Boston Chicago Major Airlines 3/17/20 3/24/20 0 $153

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

18 19 20 21 22 23 24
25 26 27 28 29 30 31
$216 $165
1 2 3 4 5 6 7
$165 $153
8 9 10 11 12 13 14
$153 $153
15 16 17 18 19 20 21
$153 $147
22 23 24 25 26 27 28

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 $169.

The average price for direct flights from Boston to Chicago is $153.

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 8 9 9 10 8 9 00:00 14:21
JetBlue 6 4 4 6 6 2 6 01:45 15:52
Spirit 1 1 1 1 1 1 1 07:57 07:57
United 9 9 9 9 9 6 8 00:13 15:10
Major Airlines 5 5 5 5 5 5 5 00:50 17:00

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 $75.

The average price for round trip flights from Boston to Chicago is $153.

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 50 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 198 direct flights from Boston to Chicago.
Question: What are the most popular Boston airlines for direct flights from Boston to Chicago?
Answer: American Airlines provides 31% 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

Airlines in Boston flying to Chicago Last modified: Aug 20, 2019 3:26 -04:00Number of routes searched: 478Number of itineraries searched: 3,684,760

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 -
JetBlue -
Major Airlines -
Spirit -
United -
American CLT
American DCA
American DFW
American JFK
Alaska LAX
Alaska PDX
Alaska SAN
Alaska SEA
Alaska SFO
JetBlue FLL
JetBlue JFK
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
Major Airlines CVG
Frontier DEN
Frontier MCO
Spirit ATL
Spirit BWI
Spirit DFW
Spirit FLL
Sun Country MSP
United DEN
United EWR
United IAD
United IAH

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.

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Cheap Flights from Boston to Chicago