Flights from Chicago to Boston, United States

From
To
City
Depart
Return
Select sites to compare prices |
  • Select all
  • Deselect all

Find Flights

Search

Enter your destination to continue
Enter depart date to continue
Enter return date to continue
Select at least 3 sites to continue
Select your depart date
Select your return date
Location services timed out
Enable Location Services Required!
Location services not available at this time
Use current location
@{prefix}@{match}@{suffix}
CityAirportCity
Did you mean flights from Boston to Chicago?

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 $202 $173
7-14 days $141 $149
14-21 days $54 $173
21-30 days $54 $115
30-60 days $118 $106
60-90 days $116 $106
90+ days $157 $150

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
April Chicago Boston Spirit 4/19/21 4/24/21 0 $202
May Chicago Boston Spirit 5/13/21 5/17/21 0 $118
June Chicago Boston Spirit 6/14/21 6/17/21 0 $116
June Chicago Boston Spirit 6/19/21 6/26/21 0 $108
August Chicago Boston !! 8/17/21 8/23/21 0 $157
August Chicago Boston Spirit 8/18/21 8/25/21 0 $115
September Chicago Boston Major Airlines 9/10/21 9/13/21 0 $141
October Chicago Boston Major Airlines 10/28/21 11/2/21 0 $141

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

SunMonTueWedThuFriSat
14 15 16 17 18 19 20
$173
21 22 23 24 25 26 27
$173 $162
28 29 30 31 1 2 3
$162
4 5 6 7 8 9 10
$79
11 12 13 14 15 16 17
$79 $79
18 19 20 21 22 23 24
$79 $79
25 26 27 28 29 30 1
$79

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 $140.

The average price for direct flights from Chicago to Boston is $202.

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 10 10 10 10 10 5 10 01:00 17:19
Major Airlines 5 5 5 5 5 3 4 01:00 14:59
United 9 9 9 9 9 5 7 01:00 16:05

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 $96.

The average price for round trip flights from Chicago to Boston is $202.

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 20 minutes.
Question: How far is Boston from Chicago?
Answer: The distance from Chicago to Boston is 863 miles (1,388 kilometers).
Question: How common are direct flights from Chicago to Boston?
Answer: There are 154 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 42% of the non-stop flights between Chicago and Boston.

Airlines in Chicago flying to Boston Last modified: Apr 19, 2021 17:52 -04:00Number of routes searched: 0Number of itineraries searched: 0

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.

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: Apr 19, 2021 17:52 -04:00

FlightsLowest Price
Chicago to Toronto$26,857
Cheap Flights from Chicago to Boston