Flights from Boston to Chicago, United States

Did you mean flights from Chicago to Boston?

Boston to Chicago Last modified: Jan 22, 2024 9:27 -05:00

We've scanned 115,678,683 round trip itineraries and found the cheapest flights to Chicago. Multiple Airlines & Frontier frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Multiple Airlines
BOSCHI
Wed 1/17
nonstop
CHIBOS
Wed 1/24
nonstop
$105
Frontier
BOSCHI
Sat 2/10
1 stop
CHIBOS
Tue 2/13
1 stop
$108
Major Airlines
BOSCHI
Mon 2/19
nonstop
CHIBOS
Thu 2/22
nonstop
$108
American
BOSCHI
Wed 2/21
nonstop
CHIBOS
Wed 2/28
nonstop
$109
JetBlue
BOSCHI
Mon 2/19
nonstop
CHIBOS
Sat 2/24
nonstop
$109
Spirit
BOSCHI
Mon 2/26
1 stop
CHIBOS
Mon 3/4
1 stop
$149

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 $126.

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 $147 $155
7-14 days $105 $116
14-21 days $107 $108
21-30 days $107 $108
30-60 days $106 $108
60-90 days $107 $116
90+ days $117 $157

Cheapest Day To Fly from Boston to Chicago

We've examined 231,357,366 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 Wednesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$107$106$105$127$107$219$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
7 8 9 10 11 12 13
$147
14 15 16 17 18 19 20
$147 $107
21 22 23 24 25 26 27
$107 $107
28 29 30 31 1 2 3
$107 $107
4 5 6 7 8 9 10
$107 $107
11 12 13 14 15 16 17
$107

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 $172.

The average price for direct flights from Boston to Chicago is $159.

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 10 10 10 10 4 10 00:00 15:25
Major Airlines 5 5 5 5 5 3 4 01:00 15:18
United 9 9 9 9 9 5 8 00:00 15:15

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 $77.

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 48 minutes.
Question: How far is Chicago from Boston?
Answer: The distance from Boston to Chicago is 863 miles (1,388 kilometers).
Question: How common are direct flights from Boston to Chicago?
Answer: There are 154 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 41% of the non-stop flights between Boston and Chicago.

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.

Cheap Flights from Boston to Chicago