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Cheap Flights from Boston to Chicago, IL, United States - BOS to CHI Last modified: May 28, 2016 6:51 AM

Popular flights from Boston to Chicago Last modified: May 28, 2016 6:51 AM

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
Jun 7, 2016 Jun 8, 2016 $107
JetBlue Airways
Departure Date Return Date Lowest Price
Jul 6, 2016 Jul 13, 2016 $147
Jul 13, 2016 Jul 26, 2016 $147
Jul 19, 2016 Jul 20, 2016 $147
Jul 19, 2016 Jul 26, 2016 $147
Jul 20, 2016 Jul 26, 2016 $147
Spirit Airlines
Departure Date Return Date Lowest Price
Aug 23, 2016 Aug 24, 2016 $81
United Airlines
Departure Date Return Date Lowest Price
Jun 7, 2016 Jun 8, 2016 $138

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 $128.

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 $120 $262
7-14 days $107 $247
14-21 days $125 $260
21-30 days $147 $251
30-60 days $147 $171
60-90 days $81 $212
90+ days $115 $212

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
$166 $81 $99 $117 $117 $154 $157

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 5/31/16 6/4/16 0 $157
June Boston Chicago American 6/7/16 6/8/16 0 $107
July Boston Chicago JetBlue 7/6/16 7/13/16 0 $147
August Boston Chicago Spirit 8/23/16 8/24/16 0 $81
September Boston Chicago Spirit 9/19/16 9/21/16 0 $115
October Boston Chicago Spirit 10/31/16 11/3/16 0 $115
November Boston Chicago Spirit 11/3/16 11/7/16 0 $117
December Boston Chicago American 12/2/16 12/4/16 0 $147

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
29 30 31 1 2 3 4
$207
5 6 7 8 9 10 11
$207 $197
12 13 14 15 16 17 18
$197 $157
19 20 21 22 23 24 25
$157 $205
26 27 28 29 30 1 2
$205 $225
3 4 5 6 7 8 9
$225

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 $222.

The average price for non-stop flights from Boston to Chicago is $130.

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 11 11 11 11 11 8 10 05:30 21:10
JetBlue 4 4 4 4 4 3 4 08:00 19:35
Spirit 1 1 1 1 1 1 1 13:22 13:22
United 9 9 9 9 8 6 9 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 $64.

The average price for round trip flights from Boston to Chicago is $130.

More Cheap Flights

FlightsAirlineLowest Price
New York to Chicago American, Alaska, JetBlue, Spirit, United $81
Newark to Chicago American, Alaska, JetBlue, United $159
Hartford to Chicago American, United $339
Providence to Chicago American, United $201
Westchester County to Chicago American, United $328
Albany to Chicago American, United $339
Burlington to Chicago American, United $358
Manchester to Chicago American, United $201
Portland to Chicago American, JetBlue, United $306
Long Island MacArthur to Chicago American $432
Newburgh to ChicagoCheck Dates
Bangor to Chicago American, United $496
New Haven to Chicago American $245
Nantucket to Chicago American, JetBlue, United $371
New York to Atlanta American, Alaska, Frontier, Spirit, United $147
New York to Los Angeles American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $292
New York to Toronto American, Air Canada, Alaska, JetBlue, Porter, United, WestJet $173
New York to Detroit American, JetBlue, Spirit, United $167
New York to London American, Air Berlin, Air France, 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 $632
New York to Milwaukee American, Alaska, United $159
New York to Dallas - Ft Worth American, Alaska, JetBlue, Spirit, United, Virgin America $81
New York to Orlando American, JetBlue, Frontier, Spirit, United $153
New York to Minneapolis - St Paul American, Sun Country, United $247
New York to Miami American, Frontier, United $135
New York to Indianapolis American, Alaska, United $143
New York to Las Vegas American, Alaska, JetBlue, Spirit, United, Virgin America $238
Boston to Atlanta American, Spirit, United $191
New York to Charlotte American, JetBlue, United $153
New York to San Francisco American, Alaska, JetBlue, Sun Country, United, Virgin America $337
Boston to New York American, JetBlue $97

Airlines Flying from Boston to Chicago (BOS to CHI) Number of flights searched: 261Last modified: May 28, 2016 6:51 AM

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 IAD X X X X X X X
Southwest - X X X X X X X
Southwest IND 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 49 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 165 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 44% 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.