Flights
Hotels
From
To
1 traveler
Unsupported Browser!
Find Flights
Flights
Hotels
1 traveler
Unsupported Browser!
Find Flights

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

Popular flights from Boston to Chicago

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

American Airlines
Departure Date Return Date Lowest Price
May 17, 2016 May 18, 2016 $87
JetBlue Airways
Departure Date Return Date Lowest Price
May 11, 2016 May 16, 2016 $105
May 14, 2016 May 16, 2016 $105
May 14, 2016 May 21, 2016 $105
Spirit Airlines
Departure Date Return Date Lowest Price
May 17, 2016 May 18, 2016 $97
United Airlines
Departure Date Return Date Lowest Price
May 10, 2016 May 17, 2016 $97

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 $106.

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 $117 $188
7-14 days $97 $168
14-21 days $87 $158
21-30 days $122 $169
30-60 days $117 $187
60-90 days $117 $210
90+ days $116 $195

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
$127 $87 $105 $107 $122 $97 $102

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
May Boston Chicago American 5/17/16 5/18/16 0 $87
June Boston Chicago Spirit 6/1/16 6/8/16 0 $117
July Boston Chicago Spirit 7/19/16 7/20/16 0 $117
August Boston Chicago Spirit 8/23/16 8/25/16 0 $117
September Boston Chicago Spirit 9/7/16 9/10/16 0 $117
October Boston Chicago Spirit 10/6/16 10/8/16 0 $117
November Boston Chicago Spirit 11/1/16 11/8/16 0 $116
December Boston Chicago United 12/1/16 12/4/16 0 $173

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
1 2 3 4 5 6 7
$117
8 9 10 11 12 13 14
$117 $97
15 16 17 18 19 20 21
$97 $107
22 23 24 25 26 27 28
$107 $137
29 30 31 1 2 3 4
$137 $167
5 6 7 8 9 10 11
$167

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 $223.

The average price for non-stop flights from Boston to Chicago is $150.

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 12 11 12 12 12 9 11 05:30 21:10
JetBlue 3 3 3 3 3 2 2 08:09 16:45
Spirit 1 1 1 1 1 1 1 13:28 13:28
United 6 8 8 8 8 5 5 06:00 19:59

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 $54.

The average price for round trip flights from Boston to Chicago is $146.

More Cheap Flights

FlightsAirlineLowest Price
New York to Chicago American, Alaska, JetBlue, Spirit, United $106
Newark to Chicago American, Alaska, JetBlue, United $185
Hartford to Chicago American, United $339
Providence to Chicago American, United $218
Westchester County to Chicago American, United $326
Albany to Chicago American, United $339
Burlington to Chicago American, United $312
Manchester to Chicago American, United $213
Portland to Chicago American, JetBlue, United $318
Long Island MacArthur to Chicago American, United $310
Newburgh to ChicagoCheck Dates
Bangor to Chicago American, United $400
New Haven to Chicago American $314
Nantucket to Chicago American, JetBlue, United $263
New York to Atlanta American, Alaska, Frontier, Spirit, United $161
New York to Los Angeles American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $210
New York to Toronto American, Air Canada, Alaska, JetBlue, Spirit, Porter, United, Virgin America, WestJet $156
New York to Detroit American, Alaska, JetBlue, Spirit, United $97
New York to London Aegean, American, Air Berlin, Air France, Alaska, Finnair, Alitalia, JetBlue, British Airways, airBaltic, Condor, OpenSkies, Aer Lingus, Iberia, Meridiana, KLM, Kuwait, Luxair, Lufthansa, LOT, Thomas Cook, Czech, Austrian, TAROM, SATA, XL Airways, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic, City Jet, Great Lakes $697
New York to Milwaukee American, United $147
New York to Dallas - Ft Worth American, Alaska, JetBlue, Spirit, United, Virgin America $128
New York to Orlando American, Alaska, JetBlue, Spirit, United $124
New York to Minneapolis - St Paul American, Sun Country, United $294
New York to Miami American, Frontier, United $126
New York to Indianapolis American, United $143
New York to Las Vegas American, Alaska, JetBlue, Spirit, United, Virgin America $236
Boston to Atlanta American, Alaska, Spirit, United $151
New York to Charlotte American, JetBlue $147
New York to San Francisco American, Alaska, JetBlue, Sun Country, United, Virgin America $272
Boston to New York American, JetBlue $129

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
Spirit - 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 CMH 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 52 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 142 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 48% 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.