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Cheap Flights from Boston to Chicago, IL, United States - BOS to CHI

Popular flights from Boston to Chicago

If your flight days are flexible and you looking for a good deal, our charts on cheap flights provide some insight regarding affordable flight options for your next big adventure.

American Airlines
Departure Date Return Date Lowest Price
Feb 25, 2016 Mar 1, 2016 $100
Feb 25, 2016 Mar 2, 2016 $100
Feb 27, 2016 Mar 1, 2016 $100
Mar 2, 2016 Mar 6, 2016 $100
Mar 3, 2016 Mar 5, 2016 $100
JetBlue Airways
Departure Date Return Date Lowest Price
Feb 29, 2016 Mar 4, 2016 $103
Spirit Airlines
Departure Date Return Date Lowest Price
May 5, 2016 May 6, 2016 $113
United Airlines
Departure Date Return Date Lowest Price
Feb 25, 2016 Mar 2, 2016 $100
Feb 25, 2016 Mar 1, 2016 $100
Mar 22, 2016 Mar 30, 2016 $100
Apr 5, 2016 Apr 12, 2016 $100
Apr 5, 2016 Apr 6, 2016 $100

How Much Does it Cost to Fly from Boston to Chicago (BOS to CHI)?

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 $101.

When Can I Buy the Cheapest Flight from Boston to Chicago (BOS to CHI)?

Airlines can adjust prices for plane 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 discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Boston to Chicago

The chart below shows up-to-date information regarding how far in advance a flight from Boston to Chicago should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $248 $255
7-14 days $100 $140
14-21 days $100 $140
21-30 days $100 $142
30-60 days $100 $139
60-90 days $100 $143
90+ days $103 $145

Cheapest Day To Fly from Boston to Chicago

The chart below shows up-to-date information regarding the cheapest days to fly from Boston to Chicago.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$103 $100 $100 $100 $103 $100 $103

Lowest Fares Chart By Month from Boston to Chicago

The chart below shows the lowest fare by month when flying from Boston to Chicago.

Month Origin Destination Carrier Depart Date Return Date Stops Price
February Boston Chicago American 2/25/16 3/1/16 0 $100
March Boston Chicago American 3/2/16 3/6/16 0 $100
April Boston Chicago American 4/6/16 4/10/16 0 $100
May Boston Chicago American 5/4/16 5/8/16 0 $100
June Boston Chicago United 6/1/16 6/4/16 0 $133
July Boston Chicago American 7/5/16 7/12/16 0 $158
August Boston Chicago American 8/12/16 8/15/16 0 $163
September Boston Chicago United 9/10/16 9/24/16 0 $160

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Boston to Chicago

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Boston to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
14 15 16 17 18 19 20
$158
21 22 23 24 25 26 27
$158 $100
28 29 1 2 3 4 5
$100 $103
6 7 8 9 10 11 12
$103 $158
13 14 15 16 17 18 19
$158 $101
20 21 22 23 24 25 26
$101

Non-Stop vs Connecting Flights from Boston to Chicago (BOS to CHI)

Your Boston to Chicago flight can be significantly cheaper by choosing 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 $141.

The average price for non-stop flights from Boston to Chicago is $113.

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

Nonstop Flight Details from Boston to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 8 8 8 8 8 6 8 05:30 18:56
JetBlue 3 3 3 3 3 2 2 06:59 16:16
United 7 7 7 7 7 5 7 06:05 20:00

Round Trip vs One Way Flights from Boston to Chicago (BOS to CHI)

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 $60.

The average price for round trip flights from Boston to Chicago is $113.

More Cheap Flights

FlightsAirlineLowest Price
New York to Chicago American, Alaska, JetBlue, Spirit, United $74
Newark to Chicago American, Alaska, JetBlue, Spirit, United $137
Hartford to Chicago American, United $264
Providence to Chicago American, United $170
Westchester County to Chicago American, United $315
Albany to Chicago American, United $326
Burlington to Chicago American, JetBlue, United $282
Manchester to Chicago American, United $173
Portland to Chicago American, JetBlue, United $294
Long Island MacArthur to Chicago American, United $275
Newburgh to Chicago Silver, American, United Check Dates
Bangor to Chicago American, United $214
New Haven to Chicago American $285
Nantucket to Chicago American, JetBlue, United Check Dates
New York to Atlanta American, Alaska, Frontier, Spirit, United $124
New York to Los Angeles American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $239
New York to Toronto American, Air Canada, Alaska, JetBlue, Porter, United, WestJet $183
New York to Detroit American, JetBlue, Spirit, United $87
New York to London American, Air Berlin, Air France, Finnair, Alitalia, JetBlue, British Airways, airBaltic, Condor, OpenSkies, Aer Lingus, Iberia, Meridiana, KLM, Kuwait, Lufthansa, LOT, Thomas Cook, Czech, Austrian, TAROM, SATA, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic $647
New York to Milwaukee American, United $145
New York to Dallas - Ft Worth American, JetBlue, Spirit, Sun Country, United, Virgin America $86
New York to Orlando American, JetBlue, Spirit, United $127
New York to Minneapolis - St Paul American, Sun Country, United $255
New York to Miami American, Frontier, United $95
New York to Indianapolis American, Alaska, United $138
New York to Las Vegas American, Alaska, JetBlue, Spirit, United, Virgin America $223
Boston to Atlanta American, Spirit, United $151
New York to Charlotte American, JetBlue, United $127
New York to San Francisco American, Alaska, JetBlue, Sun Country, United, Virgin America $236
Boston to New York American, JetBlue $97

Airlines Flying from Boston to Chicago (BOS to CHI)

Below are the different airlines that fly from Boston to Chicago with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Boston to Chicago.

Boston to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
American LGA X X X X X X X
JetBlue - X X X X X X X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
United - X X X X X X X
United EWR X X X X X X X
Southwest - X X X X X X X
Southwest BWI X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Boston and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Boston to Chicago Flight Questions

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

Question: How long is a direct flight from Boston to Chicago?
Answer: The average Boston to Chicago flight time is 2 hours and 56 minutes.
Question: How many miles are there between Boston and Chicago?
Answer: The distance from Boston to Chicago is 864 miles.
Question: How common are direct flights from Boston to Chicago?
Answer: There are 120 direct flights from Boston to Chicago.
Question: What is the most popular airline for non-stop flights from Boston to Chicago?
Answer: American Airlines provides 45% 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
Boston (BOS) To Chicago, IL (CHI) Flights: Cheap Flights From Boston To Chicago | FareCompare.