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 $33. 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 $ 33 – the departure date for this flight is 19 October 2021.

Sort by: Departure dateCheap flightsFast flightsDirect flights
01.11.2021 Monday
from $ 36 Mytrip.com
Economy Found 2021-09-30
1 Stopover 7 hours 59 min
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17.11.2021 Wednesday
from $ 43 Thefaremasters.com
Economy Found today
Nonstop 2 hours 11 min
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16.11.2021 Tuesday
from $ 43 Thefaremasters.com
Economy Found today
Nonstop 2 hours 11 min
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18.11.2021 Thursday
from $ 51 Kiwi.com
Economy Found 2 days
1 Stopover 16 hours 53 min
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17.11.2021 Wednesday
from $ 51 Kiwi.com
Economy Found today
1 Stopover 16 hours 3 min
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16.11.2021 Tuesday
from $ 51 Kiwi.com
Economy Found today
1 Stopover 21 hours 48 min
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01.11.2021 Monday
from $ 63 Mytrip.com
Economy Found 2021-09-30
Nonstop 2 hours 17 min
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18.11.2021 Thursday
from $ 65 Trip.com
Economy Found 2 days
Nonstop 2 hours 20 min
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17.11.2021 Wednesday
from $ 67 Gotogate
Economy Found today
2 Stopovers 12 hours 17 min
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18.11.2021 Thursday
from $ 68 SuperSaver
Economy Found 2 days
2 Stopovers 12 hours 17 min
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23.11.2021 Tuesday
from $ 69 FlightNetwork
Economy Found 2 days
1 Stopover 9 hours 16 min
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01.11.2021 Monday
from $ 70 Aviakassa
Economy Found 2021-09-30
2 Stopovers 38 hours 4 min
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16.11.2021 Tuesday
from $ 74 Kiwi.com
Economy Found today
2 Stopovers 18 hours 0 min
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17.11.2021 Wednesday
from $ 80 Gotogate
Economy Found today
3 Stopovers 27 hours 51 min
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18.11.2021 Thursday
from $ 81 SuperSaver
Economy Found 2 days
3 Stopovers 17 hours 48 min
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16.11.2021 Tuesday
from $ 88 FlyFar
Economy Found today
3 Stopovers 33 hours 58 min
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29.11.2021 Monday
from $ 91 Aviakassa
Economy Found 2 days
1 Stopover 29 hours 38 min
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23.11.2021 Tuesday
from $ 108 Thefaremasters.com
Economy Found 2 days
Nonstop 2 hours 17 min
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29.11.2021 Monday
from $ 110 Aviakassa
Economy Found 2 days
2 Stopovers 30 hours 0 min
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01.11.2021 Monday
from $ 111 Aviakassa
Economy Found 2021-09-30
3 Stopovers 35 hours 53 min
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29.11.2021 Monday
from $ 116 Trip.com
Economy Found 2 days
Nonstop 2 hours 17 min
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23.11.2021 Tuesday
from $ 121 Kissandfly
Economy Found 2 days
2 Stopovers 24 hours 9 min
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23.11.2021 Tuesday
from $ 123 FlightNetwork
Economy Found 2 days
3 Stopovers 25 hours 27 min
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29.11.2021 Monday
from $ 124 SuperSaver
Economy Found 2 days
3 Stopovers 25 hours 27 min
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16.11.2021 Tuesday
from $ 138 FlyFar
Economy Found today
4 Stopovers 26 hours 51 min
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28.11.2021 Sunday
from $ 150 KupiBilet.ru
Economy Found 2 days
1 Stopover 62 hours 37 min
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28.11.2021 Sunday
from $ 177 Aviakassa
Economy Found 2 days
2 Stopovers 31 hours 33 min
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28.11.2021 Sunday
from $ 230 Aviakassa
Economy Found 2 days
3 Stopovers 48 hours 33 min
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28.11.2021 Sunday
from $ 390 Trip.com
Economy Found 2 days
Nonstop 2 hours 27 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 $ 88, the flight dates are: there on 16 October 2021 year and back on 23 October 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 923 Day flight
Departure 16.10.21 12:00, Sa
1 Stopover Trip 7 days
Return 23.10.21 21:32, Sa
Spirit Airlines NK 425 Night flight
Departure 10.10.21 00:10, Su
1 Stopover Trip 2 days
Return 12.10.21 10:00, Tu
Spirit Airlines NK 923 Day flight
Departure 15.10.21 12:00, Fr
1 Stopover Trip 4 days
Return 19.10.21 10:11, Tu
JetBlue Airways B6 9521 Evening flight
Departure 29.10.21 22:32, Fr
Direct Trip 2 days
Return 31.10.21 11:00, Su
Spirit Airlines NK 923 Day flight
Departure 19.10.21 12:00, Tu
1 Stopover Trip 3 days
Return 22.10.21 10:11, Fr
Spirit Airlines NK 425 Night flight
Departure 23.10.21 00:10, Sa
1 Stopover Trip 5 days
Return 28.10.21 09:35, Th
United Airlines UA 1885 Night flight
Departure 04.01.22 03:22, Tu
1 Stopover Trip 1 day
Return 04.01.22 22:29, Tu
United Airlines UA 3513 Day flight
Departure 05.01.22 13:45, We
Direct Trip 1 day
Return 06.01.22 17:30, Th
JetBlue Airways B6 563 Morning flight
Departure 07.10.21 10:40, Th
1 Stopover Trip 7 days
Return 14.10.21 13:59, Th
United Airlines UA 656 Night flight
Departure 19.12.21 00:02, Su
1 Stopover Trip 28 days
Return 15.01.22 19:00, Sa
Spirit Airlines NK 3165 Day flight
Departure 23.11.21 12:15, Tu
1 Stopover Trip 7 days
Return 30.11.21 00:53, Tu
United Airlines UA 2654 Evening flight
Departure 23.10.21 19:00, Sa
Direct Trip 1 day
Return 24.10.21 10:00, Su
Spirit Airlines NK 923 Day flight
Departure 08.10.21 12:00, Fr
1 Stopover Trip 9 days
Return 17.10.21 10:00, Su
Spirit Airlines NK 2 Day flight
Departure 22.12.21 11:52, We
1 Stopover Trip 6 days
Return 28.12.21 03:26, Tu
American Airlines AA 1854 Day flight
Departure 19.11.21 12:00, Fr
1 Stopover Trip 8 days
Return 27.11.21 11:15, Sa
American Airlines AA 629 Day flight
Departure 02.01.22 13:15, Su
Direct Trip 1 day
Return 03.01.22 11:05, Mo
*Prices include: baggage, hand luggage, airline fees and charges.

Flight Schedule Chicago to Boston 2021

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 14 flights every day, from 2hours 14min. Local departure and arrival times are indicated.
07:4511:06
United Airlines UA3513 United Airlines UA3513
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
08:0011:37
American Airlines AA4163 American Airlines AA4163
ORD → BOS
Mo Tu We Th Fr - -
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08:1011:25
Southwest Airlines WN9 Southwest Airlines WN9
MDW → BOS
- - - - - Sa -
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08:3511:50
Southwest Airlines WN3723 Southwest Airlines WN3723
MDW → BOS
- - - - - - Su
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08:4512:00
Southwest Airlines WN2822 Southwest Airlines WN2822
MDW → BOS
- Tu We - - - -
Check price
09:3012:56
JetBlue Airways B64307 JetBlue Airways B64307
ORD → BOS
Mo Tu We Th Fr - Su
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09:5013:17
JetBlue Airways B64307 JetBlue Airways B64307
ORD → BOS
- - - - - Sa -
Check price
10:1513:45
American Airlines AA9443 American Airlines AA9443
ORD → BOS
Mo Tu We Th Fr - Su
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10:1513:45
JetBlue Airways B6312 JetBlue Airways B6312
ORD → BOS
Mo Tu We Th Fr - Su
Check price
10:5114:11
United Airlines UA677 United Airlines UA677
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
11:0014:29
Delta Air Lines DL5721 Delta Air Lines DL5721
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
12:1515:35
Southwest Airlines WN237 Southwest Airlines WN237
MDW → BOS
- - - - - Sa -
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 $ 33
13 October 2021
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
13 October 2021
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 $ 20
16 October 2021
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 $ 53
11 December 2021
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 $ 33
19 October 2021

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 $ 25
19 October 2021
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 $ 74
27 October 2021
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 $ 23
09 December 2021
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 $ 33
19 October 2021
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 $ 70
03 November 2021

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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