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?

Chicago to Boston Last modified: Oct 18, 2021 10:15 -04:00

We've scanned 1,972,836 round trip itineraries and found the cheapest flights to Boston. 00 & !! frequently offer the best deals to Boston flights, or select your preferred carrier below to see the cheapest days to fly.

00
CHIBOS
Sat 10/23
nonstop
BOSCHI
Tue 10/26
nonstop
!!
CHIBOS
Sat 10/30
nonstop
BOSCHI
Tue 11/2
nonstop
$104
United
CHIBOS
Tue 10/19
2 stops
BOSCHI
Thu 10/21
2 stops
$375

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 $90.

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 $75 $375
7-14 days $77 $163
14-21 days $86 $163
21-30 days $134 $63
30-60 days $89 $283
60-90 days $138 $683
90+ days $128 $639

Cheapest Day To Fly from Chicago to Boston

We've examined 3,945,672 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 Saturday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$84$77$89$84$120$75$95

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
October Chicago Boston 00 10/23/21 10/26/21 0 $75
November Chicago Boston 00 11/1/21 11/8/21 0 $84
December Chicago Boston 00 12/9/21 12/15/21 0 $89
January Chicago Boston 00 1/29/22 2/5/22 0 $128
February Chicago Boston !! 2/8/22 2/15/22 0 $137
March Chicago Boston 00 3/5/22 3/9/22 0 $139
April Chicago Boston 00 4/1/22 4/12/22 0 $148
May Chicago Boston 00 5/28/22 6/4/22 0 $168

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
27 28 29 30 1 2 3
$207
4 5 6 7 8 9 10
$207
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
1 2 3 4 5 6 7
8 9 10 11 12 13 14
$506
15 16 17 18 19 20 21
$506
22 23 24 25 26 27 28
29 30 31 1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
$131
24 25 26 27 28 29 30
$131 $111
31 1 2 3 4 5 6
$111
7 8 9 10 11 12 13
$134

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 $375.

The average price for direct flights from Chicago to Boston is $132.

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 $73.

The average price for round trip flights from Chicago to Boston is $140.

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.

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: Oct 18, 2021 10:15 -04:00

FlightsLowest Price
Chicago to Toronto$173
Cheap Flights from Chicago to Boston