Airfare Deals Boston to Chicago

On HolidayPrice.com you will find 6 direct and 4 connecting flights from Boston to Chicago at a price of from $14. 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 $ 14 – the departure date for this flight is 08 August 2020.

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

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 $ 32, the flight dates are: there on 14 August 2020 year and back on 17 August 2020 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 2855 Morning flight
Departure 14.08.20 07:00, Fr
Direct Trip 4 days
Return 17.08.20 22:05, Mo
Spirit Airlines NK 2855 Morning flight
Departure 07.08.20 07:00, Fr
1 transfer Trip 2 days
Return 09.08.20 12:53, Su
American Airlines AA 2024 Morning flight
Departure 13.08.20 06:00, Th
Direct Trip 1 day
Return 13.08.20 18:46, Th
Spirit Airlines NK 2855 Morning flight
Departure 28.08.20 07:00, Fr
Direct Trip 4 days
Return 31.08.20 22:05, Mo
*Prices include: baggage, hand luggage, airline fees and charges.

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 30 flights every day, from 2hours 35min. Local departure and arrival times are indicated.
05:3007:05
Southwest Airlines WN4993 Southwest Airlines WN4993
BOS → MDW
- - - - - - Su
Check price
13:0014:35
Southwest Airlines WN4811 Southwest Airlines WN4811
BOS → MDW
- - - - - - Su
Check price
05:3007:10
Southwest Airlines WN5617 Southwest Airlines WN5617
BOS → MDW
Mo Tu We Th Fr - -
Check price
06:0007:40
Southwest Airlines WN4292 Southwest Airlines WN4292
BOS → MDW
- - - - - Sa -
Check price
09:4011:20
Southwest Airlines WN205 Southwest Airlines WN205
BOS → MDW
Mo Tu We Th Fr - -
Check price
13:2515:05
Southwest Airlines WN2586 Southwest Airlines WN2586
BOS → MDW
- - - - - Sa -
Check price
20:2522:05
Southwest Airlines WN4203 Southwest Airlines WN4203
BOS → MDW
- - - - - Sa -
Check price
21:5523:35
Southwest Airlines WN5073 Southwest Airlines WN5073
BOS → MDW
- - - - - - Su
Check price
05:2507:05
United Airlines UA774 United Airlines UA774
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
09:0010:45
Southwest Airlines WN4452 Southwest Airlines WN4452
BOS → MDW
- - - - - Sa -
Check price
10:4512:30
Southwest Airlines WN6235 Southwest Airlines WN6235
BOS → MDW
- - - - - - Su
Check price
19:1020:55
Southwest Airlines WN5189 Southwest Airlines WN5189
BOS → MDW
- - - - - - Su
Check price
Show all

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

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 $ 63Chicago Midway  ~ 14 km* from $ 71

*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.

Boston - New York B6 917 JetBlue Airways Embraer 190
12:10 Boston RT128 Railway
in a way 0 hours 50 min Direct
13:00 John F. Kennedy
from $ 31 14 August 2020
Boston - Los Angeles UA 2145 United Airlines Boeing 757-200
16:45 Boston RT128 Railway
in a way 6 hours 0 min Direct
22:45 Los Angeles
from $ 46 21 September 2020
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44 Boston RT128 Railway
in a way 2 hours 16 min Direct
05:00 O'Hare
from $ 14 08 August 2020
Boston - San Francisco B6 133 JetBlue Airways Airbus A318/319/320/321
13:52 Boston RT128 Railway
in a way 6 hours 8 min Direct
20:00 San Francisco
from $ 73 06 September 2020
Boston - Orlando B6 451 JetBlue Airways Airbus A320
16:09 Boston RT128 Railway
in a way 2 hours 51 min Direct
19:00 Orlando
from $ 18 19 August 2020

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.

New York - Chicago UA 761 United Airlines Boeing 737-800
13:00 LaGuardia
in a way 2 hours 0 min Direct
15:00 O'Hare
from $ 21 21 August 2020
Los Angeles - Chicago UA 910 United Airlines Boeing 737-800
10:23 Los Angeles
in a way 3 hours 37 min Direct
14:00 O'Hare
from $ 27 02 September 2020
Miami - Chicago AA 2796 American Airlines Boeing 767-300
17:05 Miami
in a way 2 hours 55 min Direct
20:00 O'Hare
from $ 30 04 September 2020
San Francisco - Chicago UA 1800 United Airlines Airbus A319
04:15 San Francisco
in a way 3 hours 45 min Direct
08:00 O'Hare
from $ 40 23 September 2020
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44 Boston RT128 Railway
in a way 2 hours 16 min Direct
05:00 O'Hare
from $ 14 08 August 2020

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 city

To start searching for tickets, Specify dates.

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