Airfare Deals

On HolidayPrice.com you will find 6 direct and 4 connecting flights from Boston to Chicago at a price of from $38. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out BOS - CHI flight schedule to find best flight time, convenient departure and arrival airports.

The cost of airline tickets from Boston to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

One way flight from Boston to Chicago

Below are the prices of tickets for direct one-way flights from Boston to Chicago. The cheapest flight from Boston to Chicago starts from $ 38 – the departure date for this flight is 12 May 2020.

Departure date Distance Stops Business class / economy Find Ticket

25.02.20

849.41 m

Direct

Economy

Find from 45USD

25.02.20

849.41 m

1 stop

Economy

Find from 72USD

25.02.20

849.41 m

2 stops

Economy

Find from 226USD

28.02.20

849.41 m

Direct

Economy

Find from 51USD

28.02.20

849.41 m

1 stop

Economy

Find from 118USD

28.02.20

849.41 m

2 stops

Economy

Find from 282USD

06.03.20

849.41 m

Direct

Economy

Find from 70USD

06.03.20

849.41 m

1 stop

Economy

Find from 145USD

06.03.20

849.41 m

2 stops

Economy

Find from 307USD

07.03.20

849.41 m

Direct

Economy

Find from 49USD

07.03.20

849.41 m

1 stop

Economy

Find from 149USD

07.03.20

849.41 m

2 stops

Economy

Find from 264USD

09.03.20

849.41 m

Direct

Economy

Find from 45USD

09.03.20

849.41 m

1 stop

Economy

Find from 71USD

09.03.20

849.41 m

2 stops

Economy

Find from 218USD

25.03.20

849.41 m

Direct

Economy

Find from 50USD

25.03.20

849.41 m

1 stop

Economy

Find from 71USD

25.03.20

849.41 m

2 stops

Economy

Find from 213USD

26.03.20

849.41 m

Direct

Economy

Find from 60USD

26.03.20

849.41 m

1 stop

Economy

Find from 100USD

26.03.20

849.41 m

2 stops

Economy

Find from 485USD

*Prices include: baggage, hand luggage, airline fees and charges.

Flights from Boston to Chicago are most popular in June, July, August. During this period, the average price of fly tickets is from $ 103. In the low season in January, February, May, air tickets become cheaper and the average price will be from $ 76 one way.

Round trip from Boston to Chicago

You can buy a round-trip ticket from Boston to Chicago (United States) and back using the table below. The best offer starts from $ 94, the flight dates are: there on 29 April 2020 year and back on 02 May 2020 year.

Departure date Return date Airlines Flight number Stops Find Ticket

27.02.20

01.03.20

JetBlue Airways

B6 111

1 stop

Tickets from 147USD

*Prices include: baggage, hand luggage, airline fees and charges.

Cheap tickets to Chicago from Boston

The optimal cost of a flight from Boston to Chicago in both directions for each month of 2020 is shown below. The cheapest option starts from $ 94 with departure on 29 April 2020 year.

Departure date Return date Airlines Flight number Stops Find Ticket

05.03.20

06.03.20

United Airlines

UA 775

Direct

Flights from 99USD

29.04.20

02.05.20

Spirit Airlines

NK 2855

Direct

Flights from 96USD

05.05.20

14.05.20

Spirit Airlines

NK 2855

Direct

Flights from 104USD

28.07.20

01.08.20

American Airlines

AA 2387

Direct

Flights from 143USD

01.08.20

05.09.20

American Airlines

AA 544

1 stop

Flights from 201USD

11.09.20

13.09.20

American Airlines

AA 2265

Direct

Flights from 157USD

10.10.20

11.10.20

American Airlines

AA 1509

Direct

Flights from 281USD

Flight Schedule Boston to Chicago 2020

The current flight schedule for the route from Boston to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 10 flights every day, from 2hours 55min. Local departure and arrival times are indicated.
06:0008:08
American Airlines AA408 American Airlines AA408
BOS—ORD
Mo Tu - Th Fr - -
Check price
06:1008:23
Delta Air Lines DL5904 Delta Air Lines DL5904
BOS—ORD
Mo Tu We Th Fr - -
Check price
06:3508:34
United Airlines UA449 United Airlines UA449
BOS—ORD
- - - - - - Su
Check price
06:4508:46
JetBlue Airways B6111 JetBlue Airways B6111
BOS—ORD
Mo - - Th Fr Sa Su
Check price
07:0009:00
United Airlines UA449 United Airlines UA449
BOS—ORD
Mo Tu We Th Fr Sa -
Check price
08:0510:12
Delta Air Lines DL6092 Delta Air Lines DL6092
BOS—ORD
- - - - - Sa -
Check price
08:2410:24
United Airlines UA775 United Airlines UA775
BOS—ORD
Mo Tu We Th Fr Sa -
Check price
08:4010:43
JetBlue Airways B6311 JetBlue Airways B6311
BOS—ORD
Mo Tu We Th Fr - -
Check price
08:5510:50
Southwest Airlines WN4848 Southwest Airlines WN4848
BOS—MDW
- - - - - - Su
Check price
09:0011:10
American Airlines AA1239 American Airlines AA1239
BOS—ORD
Mo Tu We Th Fr Sa Su
Check price
10:0012:00
United Airlines UA1251 United Airlines UA1251
BOS—ORD
Mo Tu We Th Fr - Su
Check price
11:4213:44
Delta Air Lines DL6124 Delta Air Lines DL6124
BOS—ORD
- - - - - Sa -
Check price
Show all

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Frequently asked question

The cost of the cheapest one-way flight from Boston to Chicago starts from $ 38. The departure date of that flight is 12 May 2020.

Round trip costs start from $ 94, with the departure date there being on 29 April 2020 year, and back on 02 May 2020 year.

There are 6 airlines flying directly from Boston to Chicago: United Airlines, American Airlines, Southwest Airlines, JetBlue Airways, Delta Air Lines, Spirit Airlines

And 4 airlines fly with transfers: Southwest Airlines, JetBlue Airways, Delta Air Lines, Air Canada

The flight time from Boston to Chicago averages 02:20 mins.

13 aircraft models fly from Boston to Chicago, overcoming 847 miles in an average of 02:20 mins. The fastest aircraft on this route is Boeing 737-900 from United Airlines, it flies for 02:16 min.

  • Airbus A319
  • Airbus A320
  • Airbus A321
  • Boeing 737
  • Boeing 737-700

  • Boeing 737-800
  • Boeing 737-900
  • Boeing 757-200
  • Boeing 757-300
  • Embraer 170

  • Embraer 175
  • Embraer 190
  • Embraer EMB 175

Flight Information

Flying to Chicago from Boston takes 02:20 minutes (excluding transfers). The distance between Boston and Chicago is 847 miles (1364 kilometers). Planes depart from Boston between 00:00 and 23:55. The fastest flight from the company United Airlines with flight number UA 789. Flies for just 02:16 minutes with departure from Boston RT128 Railway and arrival in O'Hare.

time

Average flight time

02:20 min

distance

Distance

847 mi

The earliest flight

The earliest flight

00:00

The latest flight

The latest flight

23:55

Airplane

The fastest flight

02:16

Airlines

Direct flight

There are 6 airlines that fly directly from Boston to Chicago. The most popular company carrying out non-stop flights is United Airlines.

*Flight number

Flights with Transfers

Flights with transfers from Boston to Chicago can be bought from 4 airlines:

  • Southwest Airlines: Baltimore
  • JetBlue Airways: Cleveland, Baltimore, Pittsburgh
  • Delta Air Lines: New York
  • Air Canada: Hamilton

*Transit cities

Airports

Airports serving the air communication between Boston and Chicago. You can fly to Chicago from 1 Boston airports. Planes arrive at 2 airport in Chicago.

Boston airports:

Boston RT128 Railway  ~ 4 km*

Chicago airports:

O'Hare  ~ 25 km* from $ 76Chicago Midway  ~ 14 km* from $ 85

*Distance from the airport to the city center

Aircraft

You can fly from Boston to Chicago on board of 6 airlines that utilize 13 aircraft models.

  • Airbus A319
  • Airbus A320
  • Airbus A321
  • Boeing 737
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900
  • Boeing 757-200
  • Boeing 757-300
  • Embraer 170
  • Embraer 175
  • Embraer 190
  • Embraer EMB 175

Connecting cities

The list of cities on transfer flights to Chicago from Boston. The best options are to fly through: Baltimore, Cleveland, New York, Hamilton, Pittsburgh, Detroit.

Cheap airline tickets from Boston to United States

Here is a list of flights from Boston to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Origin-DestinationDepartureArrivalFlightAircraftDatePrice
Boston - New York12:1013:00B6 917Embraer 19010 May 2020
from $ 68
Boston - Los Angeles16:4522:45UA 2145Boeing 757-20003 March 2020
from $ 58
Boston - Miami03:5006:58B6 221Airbus A32001 April 2020
from $ 51
Boston - Chicago02:4405:00UA 789Boeing 737-90012 May 2020
from $ 38
Boston - San Francisco13:5220:00B6 133Airbus A318/319/320/32113 May 2020
from $ 110

All flights from Boston

Flights from United States to Chicago

Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

Origin-DestinationDepartureArrivalFlightAircraftDatePrice
New York - Chicago13:0015:00UA 761Boeing 737-80011 March 2020
from $ 37
Los Angeles - Chicago10:2314:00UA 910Boeing 737-80021 April 2020
from $ 50
Miami - Chicago17:0520:00AA 2796Boeing 767-30005 March 2020
from $ 30
San Francisco - Chicago04:1508:00UA 1800Airbus A319
Find
Boston - Chicago02:4405:00UA 789Boeing 737-90012 May 2020
from $ 38

All flights to Chicago

Tips for buying a ticket

Boston – Chicago – Boston round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Boston to Chicago Chicago

Last minute and special deals from airlines

If there are no promotions and discounts on tickets to Chicago from Boston right now, subscribe and we will notify you of price drops via e-mail (without spam, you can unsubscribe from the newsletter at any time).

To start searching for tickets, Specify dates.

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