Flights from Chicago to Boston, United States

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Did you mean flights from Boston to Chicago?

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

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

Sat 9/7
Wed 9/11
Major Airlines
Sat 10/5
Tue 10/15
Fri 9/6
Wed 9/11
Wed 10/30
Sun 11/3
Sat 9/21
Tue 9/24

How Much is a Flight from Chicago to Boston?

We have collected flight cost data from across the web for travel from Chicago to Boston, and have found the average flight price for this trip to be $151.

Where To Buy Cheap Flights from Chicago to Boston?

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 Chicago to Boston 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 Chicago to Boston?

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

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $153 $160
7-14 days $153 $160
14-21 days $147 $155
21-30 days $147 $156
30-60 days $147 $156
60-90 days $147 $160
90+ days $147 $156

Cheapest Day To Fly from Chicago to Boston

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 Chicago to Boston is Thursday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday

Compare Flight Prices from Chicago to Boston 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 Chicago to Boston flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
August Chicago Boston American 8/27/19 8/29/19 0 $153
September Chicago Boston American 9/12/19 9/15/19 0 $147
October Chicago Boston American 10/19/19 11/1/19 0 $147
November Chicago Boston American 11/1/19 11/3/19 0 $153
December Chicago Boston American 12/3/19 12/6/19 0 $153
January Chicago Boston American 1/12/20 1/21/20 0 $147
February Chicago Boston American 2/1/20 2/8/20 0 $153
March Chicago Boston Major Airlines 3/17/20 3/24/20 0 $153

Cheap Last Minute Flights from Chicago to Boston

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Boston. 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 $200
1 2 3 4 5 6 7
$200 $153
8 9 10 11 12 13 14
$153 $147
15 16 17 18 19 20 21
$147 $153
22 23 24 25 26 27 28

Connecting Flights vs Direct Flights from Chicago to Boston

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 Chicago to Boston is $169.

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

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

Weekly Direct Flights from Chicago to Boston - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 9 8 9 10 9 8 10 01:00 16:55
JetBlue 6 4 4 6 6 2 6 00:40 15:40
Spirit 1 1 1 1 1 1 1 08:46 08:46
United 9 9 9 9 9 6 8 00:58 16:19
Major Airlines 5 5 5 5 5 5 5 01:05 17:10

One Way Flights vs Round Trip Flights from Chicago to Boston

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 Chicago to Boston. 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 Chicago to Boston is $75.

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

Chicago to Boston Flight Questions

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

Question: How long is the flight from Chicago to Boston?
Answer: The average Chicago to Boston flight time is 2 hours and 24 minutes.
Question: How far is Boston from Chicago?
Answer: The distance from Chicago to Boston is 858 miles (1,380 kilometers).
Question: How common are direct flights from Chicago to Boston?
Answer: There are 197 direct flights from Chicago to Boston.
Question: What are the most popular Chicago airlines for direct flights from Chicago to Boston?
Answer: American Airlines provides 31% of the non-stop flights between Chicago and Boston.
Question: What are the most popular connecting cities when flying from Chicago to Boston?
Answer: Detroit, MI

Airlines in Chicago flying to Boston Last modified: Aug 20, 2019 3:20 -04:00Number of routes searched: 467Number of itineraries searched: 4,100,814

Wondering which airlines fly out of Chicago to Boston? We've gathered the average price of Chicago airlines with flights to Boston. 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.

Chicago to Boston
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
Spirit ATL
Spirit BWI
Spirit DFW
Spirit FLL
Sun Country MSP
United DEN
United EWR
United IAD
United IAH

Chicago to Boston Airports

These are the major commercial airports we're currently monitoring in Chicago and Boston. 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.

Cheap International Flights from Chicago - CHI Last modified: Aug 20, 2019 3:20 -04:00

FlightsLowest Price
Chicago to Toronto$215

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Cheap Flights from Chicago to Boston