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 $20. 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 $ 20 – the departure date for this flight is 05 May 2021.

Sort by: Departure dateCheap flightsFast flightsDirect flights
05.05.2021 Wednesday
from $ 20 Gotogate
Economy Found 2021-03-31
Nonstop 2 hours 23 min
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05.05.2021 Wednesday
from $ 62 FlightNetwork
Economy Found 2021-03-31
2 Stopovers 9 hours 18 min
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05.05.2021 Wednesday
from $ 65 Kiwi.com
Economy Found 2021-03-31
1 Stopover 6 hours 9 min
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03.05.2021 Monday
from $ 74 Vayama
Economy Found yesterday
1 Stopover 4 hours 2 min
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03.05.2021 Monday
from $ 96 MyHolidays
Economy Found yesterday
Nonstop 2 hours 46 min
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03.05.2021 Monday
from $ 131 Kissandfly.com
Economy Found yesterday
2 Stopovers 45 hours 19 min
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03.05.2021 Monday
from $ 138 Kissandfly.com
Economy Found yesterday
3 Stopovers 25 hours 35 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 $ 39, the flight dates are: there on 08 May 2021 year and back on 15 May 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 1052 Evening flight
Departure 10.05.21 20:22, Mo
Direct Trip 5 days
Return 15.05.21 19:37, Sa
Spirit Airlines NK 1011 Day flight
Departure 07.05.21 14:09, Fr
1 Stopover Trip 3 days
Return 10.05.21 17:22, Mo
Spirit Airlines NK 1052 Evening flight
Departure 28.05.21 20:22, Fr
Direct Trip 5 days
Return 02.06.21 19:37, We
Spirit Airlines NK 1052 Evening flight
Departure 04.06.21 20:22, Fr
1 Stopover Trip 4 days
Return 09.06.21 04:10, We
American Airlines AA 637 Day flight
Departure 20.04.21 14:30, Tu
1 Stopover Trip 3 days
Return 23.04.21 03:53, Fr
Spirit Airlines NK 1932 Day flight
Departure 17.08.21 14:00, Tu
1 Stopover Trip 6 days
Return 23.08.21 17:24, Mo
Allegiant Air G4 929 Night flight
Departure 10.04.21 00:53, Sa
1 Stopover Trip 1 day
Return 11.04.21 12:40, Su
Sun Country Airlines SY 262 Night flight
Departure 29.05.21 01:05, Sa
2 Stopovers Trip 5 days
Return 02.06.21 19:37, We
American Airlines AA 1194 Day flight
Departure 11.04.21 13:15, Su
Direct Trip 2 days
Return 13.04.21 17:49, Tu
Spirit Airlines NK 1932 Day flight
Departure 08.07.21 14:00, Th
1 Stopover Trip 3 days
Return 11.07.21 14:05, Su
American Airlines AA 2784 Evening flight
Departure 09.04.21 18:07, Fr
2 Stopovers Trip 2 days
Return 11.04.21 12:22, Su
*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 6 flights every day, from 2hours 11min. Local departure and arrival times are indicated.
08:4012:14
American Airlines AA4888 American Airlines AA4888
ORD → BOS
Mo - - Th Fr - Su
Check price
09:0512:32
United Airlines UA3528 United Airlines UA3528
ORD → BOS
- - - - - Sa -
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09:2012:47
United Airlines UA5345 United Airlines UA5345
ORD → BOS
- Tu We - - - -
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09:5013:05
Southwest Airlines WN2558 Southwest Airlines WN2558
MDW → BOS
Mo Tu We Th Fr - Su
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10:5514:22
United Airlines UA3528 United Airlines UA3528
ORD → BOS
Mo - - Th Fr - Su
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11:3114:42
JetBlue Airways B6312 JetBlue Airways B6312
ORD → BOS
Mo Tu We Th Fr Sa Su
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13:3517:05
American Airlines AA4756 American Airlines AA4756
ORD → BOS
- - - Th Fr - Su
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13:3516:50
Southwest Airlines WN2255 Southwest Airlines WN2255
MDW → BOS
Mo Tu We Th Fr - Su
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14:3017:42
United Airlines UA1752 United Airlines UA1752
ORD → BOS
Mo Tu We Th Fr - Su
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14:4018:07
United Airlines UA3583 United Airlines UA3583
ORD → BOS
- - - - - Sa -
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14:5518:10
Southwest Airlines WN4477 Southwest Airlines WN4477
MDW → BOS
- - - - - Sa -
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16:3619:56
American Airlines AA1304 American Airlines AA1304
ORD → BOS
- Tu We - - - -
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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 $ 28
11 May 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 $ 34
11 May 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 $ 21
20 April 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 $ 49
12 May 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 $ 20
05 May 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 $ 28
12 May 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 $ 88
08 June 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 $ 18
08 April 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 $ 20
05 May 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 $ 82
27 April 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

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