Airfare Deals Chicago to Boston

On HolidayPrice.com you will find 6 direct and 3 connecting flights from Chicago to Boston 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 CHI - BOS flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Chicago to Boston (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 Boston.

One way flight from Chicago to Boston

Below are the prices of tickets for direct one-way flights from Chicago to Boston. The cheapest flight from Chicago to Boston starts from $ 38 – the departure date for this flight is 21 January 2022.

Sort by: Departure dateCheap flightsFast flightsDirect flights
03.02.2022 Thursday
from $ 43 Trip.com
Economy Found 2022-01-04
Nonstop 2 hours 22 min
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03.02.2022 Thursday
from $ 62 Kiwi.com
Economy Found 2022-01-04
1 Stopover 4 hours 43 min
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03.02.2022 Thursday
from $ 97 Aviakassa
Economy Found 2022-01-04
3 Stopovers 45 hours 41 min
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03.02.2022 Thursday
from $ 107 KupiBilet.ru
Economy Found 2022-01-04
2 Stopovers 11 hours 40 min
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*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Chicago to Boston

You can buy a round-trip ticket from Chicago to Boston (United States) and back using the table below. The best offer starts from $ 83, the flight dates are: there on 21 January 2022 year and back on 24 January 2022 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
United Airlines UA 2129 Day flight
Departure 21.01.22 13:45, Fr
Direct Trip 3 days
Return 24.01.22 23:30, Mo
American Airlines AA 4307 Day flight
Departure 18.01.22 16:45, Tu
Direct Trip 14 days
Return 01.02.22 10:56, Tu
American Airlines AA 2264 Day flight
Departure 04.02.22 16:45, Fr
Direct Trip 2 days
Return 06.02.22 12:25, Su
JetBlue Airways B6 9475 Evening flight
Departure 24.01.22 20:25, Mo
Direct Trip 4 days
Return 28.01.22 16:40, Fr
American Airlines AA 2264 Day flight
Departure 14.01.22 16:45, Fr
Direct Trip 2 days
Return 16.01.22 12:25, Su
American Airlines AA 629 Day flight
Departure 17.03.22 13:05, Th
Direct Trip 5 days
Return 22.03.22 09:00, Tu
American Airlines AA 629 Day flight
Departure 15.03.22 13:05, Tu
Direct Trip 3 days
Return 18.03.22 09:00, Fr
American Airlines AA 2264 Day flight
Departure 17.02.22 16:45, Th
Direct Trip 6 days
Return 23.02.22 10:56, We
JetBlue Airways B6 906 Evening flight
Departure 20.05.22 22:31, Fr
1 Stopover Trip 1 day
Return 22.05.22 10:05, Su
Delta Air Lines DL 512 Evening flight
Departure 22.04.22 21:50, Fr
1 Stopover Trip 4 days
Return 26.04.22 21:15, Tu
United Airlines UA 2458 Night flight
Departure 19.03.22 01:40, Sa
Direct Trip 1 day
Return 20.03.22 09:00, Su
Southwest Airlines WN 2130 Day flight
Departure 10.06.22 13:40, Fr
1 Stopover Trip 3 days
Return 13.06.22 09:15, Mo
Volaris Y4 935 Morning flight
Departure 18.12.22 06:19, Su
2 Stopovers Trip 6 days
Return 24.12.22 03:35, Sa
*Prices include: baggage, hand luggage, airline fees and charges.

Flight Schedule Chicago to Boston 2022

The current flight schedule for the route from Chicago to Boston 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 25 flights every day, from 2hours 10min. Local departure and arrival times are indicated.
06:3009:45
Southwest Airlines WN2737 Southwest Airlines WN2737
MDW → BOS
- - - - - Sa -
Check price
07:0010:18
Delta Air Lines DL5715 Delta Air Lines DL5715
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
07:3010:56
American Airlines AA3535 American Airlines AA3535
ORD → BOS
Mo Tu We Th Fr Sa -
Check price
07:3010:52
United Airlines UA1844 United Airlines UA1844
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
08:1011:34
American Airlines AA4146 American Airlines AA4146
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
08:3011:45
Southwest Airlines WN4533 Southwest Airlines WN4533
MDW → BOS
- - - - - - Su
Check price
09:0012:30
United Airlines UA3706 United Airlines UA3706
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
09:4012:59
Delta Air Lines DL5708 Delta Air Lines DL5708
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
09:4012:55
Southwest Airlines WN5037 Southwest Airlines WN5037
MDW → BOS
Mo Tu We Th Fr - -
Check price
09:4513:04
American Airlines AA2264 American Airlines AA2264
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
10:1913:42
American Airlines AA9475 American Airlines AA9475
ORD → BOS
Mo Tu We Th Fr - Su
Check price
10:1913:42
JetBlue Airways B6312 JetBlue Airways B6312
ORD → BOS
Mo Tu We Th Fr - Su
Check price
Show all

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

Flight Information

Flying to Boston from Chicago takes 02:20 minutes (excluding transfers). The distance between Chicago and Boston is 847 miles (1364 kilometers). Planes depart from Chicago between 00:00 and 23:55. The fastest flight from the company United Airlines with flight number UA 1420. Flies for just 01:55 minutes with departure from O'Hare and arrival in Boston RT128 Railway.

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

01:55

Airlines

Direct flight

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

*Flight number

Flights with Transfers

Flights with transfers from Chicago to Boston can be bought from 3 airlines:

  • Southwest Airlines: Detroit, Cleveland, Nashville
  • American Airlines: Detroit, Saint Paul Island, Nashville
  • United Airlines: Detroit, Hamilton, Saint Paul Island

*Transit cities

Airports

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

Chicago airports:

Chicago Midway  ~ 14 km* from $ 71O'Hare  ~ 25 km* from $ 63

Boston airports:

Boston RT128 Railway  ~ 4 km*

*Distance from the airport to the city center

Aircraft

You can fly from Chicago to Boston on board of 6 airlines that utilize 12 aircraft models.

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

Connecting cities

The list of cities on transfer flights to Boston from Chicago. The best options are to fly through: Detroit, Saint Paul Island, Cleveland, Nashville.

Cheap airline tickets from Chicago to United States

Here is a list of flights from Chicago 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.

Chicago - New York AA 2382 American Airlines Boeing 737-800
01:13 O'Hare
in a way 1 hours 47 min Direct
03:00 Newark Liberty
Flights
from $ 39
01 March 2022
Chicago - Los Angeles AA 2744 American Airlines Airbus A321
20:03 O'Hare
in a way 3 hours 57 min Direct
00:00 Los Angeles
Flights
from $ 27
16 February 2022
Chicago - Miami WN 1909 Southwest Airlines Boeing 737-700
13:40 Chicago Midway
in a way 2 hours 55 min Direct
16:35 Fort Lauderdale Executive Airport
Flights
from $ 26
19 January 2022
Chicago - San Francisco AA 1312 American Airlines Boeing 737-800
17:55 O'Hare
in a way 4 hours 5 min Direct
22:00 Norman Y. Mineta San Jose
Flights
from $ 63
28 January 2022
Chicago - Boston UA 1420 United Airlines Airbus A320
17:05 O'Hare
in a way 1 hours 55 min Direct
19:00 Boston RT128 Railway
Flights
from $ 38
21 January 2022

All flights from Chicago

Flights from United States to Boston

Here are the cheapest flight bookings from United States to Boston 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 - Boston AA 2121 American Airlines Embraer 190
16:00 LaGuardia
in a way 1 hours 0 min Direct
17:00 Boston RT128 Railway
Flights
from $ 24
01 February 2022
Los Angeles - Boston B6 504 JetBlue Airways Airbus A320
08:00 Long Beach Airport
in a way 5 hours 14 min Direct
13:14 Boston RT128 Railway
Flights
from $ 53
22 February 2022
Miami - Boston B6 22 JetBlue Airways Airbus A320
03:12 Palm Beach
in a way 2 hours 56 min Direct
06:08 Boston RT128 Railway
Flights
from $ 22
28 January 2022
Chicago - Boston UA 1420 United Airlines Airbus A320
17:05 O'Hare
in a way 1 hours 55 min Direct
19:00 Boston RT128 Railway
Flights
from $ 38
21 January 2022
San Francisco - Boston B6 834 JetBlue Airways Airbus A318/319/320/321
06:35 San Francisco
in a way 5 hours 26 min Direct
12:01 Boston RT128 Railway
Flights
from $ 74
30 January 2022

All flights to Boston

Tips for buying a ticket

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

Cheap flights from Chicago to Boston
Boston city

To start searching for tickets, Specify dates.

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